As filed with the Securities and Exchange Commission on August 24, 2022

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

_____________________

Amendment No. 4 to
FORM S-4
REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933

_____________________

Delwinds Insurance Acquisition Corp.
(Exact name of registrant as specified in its charter)

_____________________

One City Centre
1021 Main Street, Suite 1960
Houston, Texas 77002
(713) 337-4077
(Address, including zip code, and telephone number, including area code, of registrant’s principal executive offices)

_____________________

Andrew J. Poole
Chief Executive Officer
One City Centre
1021 Main Street, Suite 1960
Houston, Texas 77002
(713) 337-4077
(Name, address, including zip code, and telephone number, including area code, of agent for service)

_____________________

Copies to:

_____________________

Approximate date of commencement of proposed sale to the public: As soon as practicable after this Registration Statement becomes effective and after all conditions under the Merger Agreement to consummate the proposed merger are satisfied or waived.

If the securities being registered on this Form are being offered in connection with the formation of a holding company and there is compliance with General Instruction G, check the following box: ☐

If this Form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering: ☐

If this Form is a post-effective amendment filed pursuant to Rule 462(d) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering: ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 7(a)(2)(B) of the Securities Act. ☐

If applicable, place an X in the box to designate the appropriate rule provision relied upon in conducting this transaction:

Exchange Act Rule 13e-4(i) (Cross-Border Issuer Tender Offer) ☐

Exchange Act Rule 14d-1(d) (Cross-Border Third-Party Tender Offer) ☐

The information in this preliminary joint proxy statement/consent solicitation statement/prospectus is not complete and may be changed. These securities may not be issued until the registration statement filed with the Securities and Exchange Commission is effective. This preliminary joint proxy statement/consent solicitation statement/prospectus is not an offer to sell these securities and does not constitute the solicitation of offers to buy these securities in any jurisdiction where the offer or sale is not permitted.

You will not be charged for any of these documents that you request. Stockholders requesting documents should do so by [__________], 2022 in order to receive them before the Delwinds Special Meeting.

The Delwinds Board formed a special committee comprised entirely of independent and disinterested directors (the “Special Committee”) to consider and negotiate the terms and conditions of the Business Combination and to recommend to the Delwinds Board whether to pursue the Business Combination and, if so, on what terms and conditions.

After careful consideration, the Delwinds Board, based in part on the unanimous recommendation of the Special Committee, has unanimously approved the Merger Agreement and the Business Combination and determined that each of the Proposals described in the accompanying joint proxy statement/consent solicitation statement/prospectus is in the best interests of Delwinds and recommends that you vote “FOR” each of these Proposals.

The accompanying joint proxy statement/consent solicitation statement/prospectus provides Delwinds stockholders with detailed information about the Business Combination and other matters to be considered at the Delwinds Special Meeting. Delwinds urges you to read the accompanying joint proxy statement/consent solicitation statement/prospectus, including the financial statements and annexes and other documents referred to therein, carefully and in their entirety. In particular, when you consider the recommendation regarding these Proposals by the Special Committee and the Delwinds Board, you should keep in mind that Delwinds’ directors and officers have interests in the Business Combination that are different from or in addition to, or may conflict with, your interests as a Delwinds stockholder. For instance, rather than liquidating Delwinds, the Sponsor will benefit from the completion of the Business Combination and may be incentivized to complete the Business Combination, even if the transaction is unfavorable to stockholders of Delwinds. In addition, you should carefully consider the matters discussed under “Risk Factors” beginning on page 56 of the accompanying joint proxy statement/consent solicitation statement/prospectus. See also the section entitled “The Business Combination Proposal — Certain Interests of Delwinds’ Directors and Officers and Others in the Business Combination” for additional information.

Stockholders should be aware that, effective as of June 8, 2022, RBC Capital Markets, LLC (“RBCCM”) has resigned from its role as Delwinds’ financial advisor and capital markets advisor, and has informed Delwinds that RBCCM waives the deferred portion of the underwriting fees to which RBCCM would otherwise have been entitled under the Underwriting Agreement dated December 10, 2020, entered into at the time of Delwinds’ initial public offering by Delwinds and its IPO Underwriters, including RBCCM, in connection with the Business Combination. Stockholders should also be aware that, effective June 16, 2022, Deutsche Bank Securities Inc. (“DB”) has resigned from its roles as financial advisor to FOXO in connection with the Business Combination. Each of RBCCM and DB has delivered notice of its resignation to the U.S. Securities and Exchange Commission pursuant to Section 11(b)(1) of the Securities Act of 1933, as amended, and has disclaimed any responsibility for any portion of the accompanying joint proxy statement/consent solicitation/prospectus. Stockholders should not place any reliance on the participation of either RBCCM or DB prior to such resignations and waivers, in the transactions contemplated by this joint proxy statement/consent solicitation/prospectus.

Your vote is very important.    To ensure your representation at the Delwinds Special Meeting, please complete and return the enclosed proxy card or submit your proxy by following the instructions contained in the accompanying joint proxy statement/consent solicitation statement/prospectus and on your proxy card. Please submit your proxy promptly whether or not you expect to participate in the meeting. Submitting a proxy now will NOT prevent you from being able to vote online during the virtual Delwinds Special Meeting. If you hold your shares in “street name,” you should instruct your broker, bank or other nominee how to vote in accordance with the voting instruction form you receive from your broker, bank or other nominee.

If you return your proxy card signed and without an indication of how you wish to vote, your shares will be voted in favor of each of the Proposals and for the election of each of the directors proposed by Delwinds for election.

TO EXERCISE YOUR REDEMPTION RIGHTS, YOU MUST (1) IF YOU HOLD SHARES OF DELWINDS CLASS A COMMON STOCK THROUGH UNITS, SEPARATE YOUR UNITS INTO THE UNDERLYING SHARES OF DELWINDS CLASS A COMMON STOCK AND PUBLIC WARRANTS PRIOR TO EXERCISING YOUR REDEMPTION RIGHTS WITH RESPECT TO THE PUBLIC SHARES, (2) SUBMIT A WRITTEN REQUEST, INCLUDING THE LEGAL NAME, PHONE NUMBER AND ADDRESS OF THE BENEFICIAL OWNER OF THE SHARES FOR WHICH REDEMPTION IS REQUESTED, TO THE TRANSFER AGENT AT LEAST TWO BUSINESS DAYS PRIOR TO THE DATE OF THE DELWINDS SPECIAL MEETING, THAT YOUR PUBLIC SHARES BE REDEEMED FOR CASH AND (3) DELIVER YOUR STOCK CERTIFICATES (IF ANY) AND OTHER REDEMPTION FORMS TO THE TRANSFER AGENT, PHYSICALLY OR ELECTRONICALLY USING THE DEPOSITORY TRUST COMPANY’S DWAC (DEPOSIT/WITHDRAWAL AT CUSTODIAN) SYSTEM, IN EACH CASE, IN ACCORDANCE WITH THE PROCEDURES AND DEADLINES DESCRIBED IN THE JOINT PROXY STATEMENT/CONSENT SOLICITATION STATEMENT/PROSPECTUS. IF THE BUSINESS COMBINATION IS NOT CONSUMMATED, THEN THE PUBLIC SHARES WILL NOT BE REDEEMED FOR CASH. IF YOU HOLD THE SHARES IN STREET NAME, YOU WILL NEED TO INSTRUCT THE ACCOUNT EXECUTIVE AT YOUR BANK, BROKER OR OTHER NOMINEE TO WITHDRAW THE SHARES FROM YOUR ACCOUNT IN ORDER TO EXERCISE YOUR REDEMPTION RIGHTS. SEE “THE DELWINDS SPECIAL MEETING — REDEMPTION RIGHTS” IN THE JOINT PROXY STATEMENT/CONSENT SOLICITATION STATEMENT/PROSPECTUS FOR MORE SPECIFIC INSTRUCTIONS.

Neither the U.S. Securities and Exchange Commission nor any state securities commission has approved or disapproved of the Business Combination or the other transactions contemplated thereby, as described in the accompanying joint proxy statement/consent solicitation statement/prospectus, or passed upon the adequacy or accuracy of the disclosure in the accompanying joint proxy statement/consent solicitation statement/prospectus. Any representation to the contrary is a criminal offense.

The accompanying joint proxy statement/consent solicitation statement/prospectus is dated [            ], 2022, and is first being mailed to stockholders of Delwinds on or about [            ], 2022.

LETTER TO FOXO STOCKHOLDERS

To the Stockholders of FOXO Technologies Inc.:

Pursuant to an Agreement and Plan of Merger, dated as of February 24, 2022 (as amended on April 26, 2022, July 6, 2022 and August 12, 2022, and as it may be further amended or supplemented from time to time, the “Merger Agreement”), by and among Delwinds Insurance Acquisition Corp., a Delaware corporation (“Delwinds”), DWIN Merger Sub Inc., a Delaware corporation and wholly-owned subsidiary of Delwinds (“Merger Sub”), DIAC Sponsor LLC, a Delaware limited liability company (the “Sponsor”), as Purchaser Representative for the purposes described in the Merger Agreement, and FOXO Technologies Inc., a Delaware corporation (“FOXO”), Merger Sub will merge with and into FOXO (the “Merger” and, collectively with the other transactions contemplated by the Merger Agreement, the “Business Combination”), with FOXO surviving the merger as a wholly-owned subsidiary of Delwinds. At the effective time of the Merger (the “Effective Time”), all shares of FOXO stock issued and outstanding immediately prior to the Effective Time will be cancelled and exchanged for the right to receive shares of Delwinds following the consummation of the Business Combination, as provided in the Merger Agreement and as more particularly described in the accompanying joint proxy statement/consent solicitation statement/prospectus. Upon the consummation of the Business Combination, Delwinds will change its name to “FOXO Technologies Inc.”

The accompanying joint proxy statement/consent solicitation statement/prospectus is being delivered to you on behalf of FOXO’s board of directors to request that FOXO’s stockholders as of the record date of August 19, 2022 execute and return written consents to adopt the Merger Agreement and approve the Business Combination.

The joint proxy statement/consent solicitation statement/prospectus describes the proposed Business Combination and the actions to be taken in connection with the Business Combination and provides additional information about the parties involved. Please give this information your careful attention. A copy of the Merger Agreement is attached as Annex A to the accompanying joint proxy statement/consent solicitation statement/prospectus.

A summary of the appraisal rights that may be available to you is described in the joint proxy statement/consent solicitation statement/prospectus in the subsection entitled “FOXO’s Solicitation of Written Consents — Appraisal Rights of FOXO Stockholders.” Please note that if you wish to exercise appraisal rights, you must not sign and return a written consent adopting the Merger Agreement. However, so long as you do not return a consent form at all, it is not necessary to affirmatively vote against or disapprove the Business Combination. In addition, you must take all other steps necessary to perfect your appraisal rights, as described in the aforementioned section of the joint proxy statement/consent solicitation statement/prospectus.

FOXO’s board of directors has considered the Business Combination and the terms of the Merger Agreement and has determined unanimously that the Business Combination and the Merger Agreement are fair to and in the best interests of FOXO and FOXO’s stockholders and recommends that FOXO’s stockholders adopt the Merger Agreement and approve the Business Combination by submitting a written consent. As described in the joint proxy statement/consent solicitation statement/prospectus, certain stockholders of FOXO, whose ownership interests collectively represent the outstanding shares of FOXO common stock and FOXO preferred stock sufficient to approve the Business Combination on behalf of FOXO, are parties to a voting agreement with Delwinds whereby such stockholders agreed to vote all of their shares of FOXO common stock and FOXO preferred stock in favor of approving the Business Combination and other proposed transactions contemplated by the Merger Agreement.

Please complete, date and sign the written consent furnished with the joint proxy statement/ prospectus and return it promptly to FOXO by one of the means described in the section entitled “FOXO’s Solicitation of Written Consents.”

If you have any questions concerning the Merger Agreement, the Business Combination, the consent solicitation or the accompanying joint proxy statement/consent solicitation statement/prospectus, or if you have any questions about how to deliver your written consent, please email investors@foxotechnologies.com or contact FOXO Technologies Inc. at 220 South Sixth Street, Suite 1200, Minneapolis, Minnesota 55402, Attention: Chief Executive Officer.

Delwinds Insurance Acquisition Corp.
One City Centre
1021 Main Street, Suite 1960
Houston, Texas 77002

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS
To Be Held On [            ], 2022
, Eastern Time

, 2022

TO THE STOCKHOLDERS OF DELWINDS INSURANCE ACQUISITION CORP.:

NOTICE IS HEREBY GIVEN that a special meeting of stockholders (the “Delwinds Special Meeting”) of Delwinds Insurance Acquisition Corp., a Delaware corporation (“Delwinds”), will be held virtually at [______] Eastern Time on [_____], 2022. The Delwinds Special Meeting shall be deemed to be a special meeting in lieu of the 2022 annual meeting of stockholders of Delwinds. The Delwinds Board has determined to convene and conduct the Delwinds Special Meeting in a virtual meeting format at https://www.cstproxy.com/delwinds/sm2022. Stockholders will NOT be able to attend the Delwinds Special Meeting in-person. The accompanying joint proxy statement/consent solicitation statement/prospectus includes instructions on how to access the virtual Delwinds Special Meeting and how to listen and vote from home or any remote location with Internet connectivity. You or your proxy holder will be able to attend and vote at the Delwinds Special Meeting by visiting https://www.cstproxy.com/delwinds/sm2022 and using a control number assigned by Continental Stock Transfer & Trust Company. The Delwinds Special Meeting will be held for the purpose of considering and voting on the proposals (the “Proposals”) described below and in the accompanying joint proxy statement/consent solicitation statement/prospectus. To register and receive access to the virtual meeting, registered stockholders and beneficial stockholders of Delwinds (those holding shares through a stock brokerage account or by a bank or other holder of record) will need to follow the instructions applicable to them provided in the accompanying joint proxy statement/consent solicitation statement/prospectus. At the Delwinds Special Meeting, Delwinds stockholders will be asked to consider and vote upon the following Proposals:

(i)      The NTA Proposal (Proposal 1) — To consider and vote on amendments to the current Certificate of Incorporation of Delwinds (the “Current Charter”), which amendments (the “NTA Amendments”) shall be effective, if adopted and implemented by Delwinds, prior to the consummation of the proposed Business Combination, to remove from the Current Charter requirements limiting Delwinds’ ability to redeem shares of Delwinds Class A common stock and consummate an initial business combination if the amount of such redemptions would cause Delwinds to have less than $5,000,001 in net tangible assets. The NTA Proposal is conditioned upon the approval of the Business Combination Proposal. Therefore, if the Business Combination Proposal is not approved, then the NTA Proposal will have no effect, even if approved by Delwinds stockholders. The NTA Proposal is described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “The NTA Proposal (Proposal 1).”

(ii)    The Business Combination Proposal (Proposal 2) — To consider and vote on a proposal to approve the Agreement and Plan of Merger, dated as of February 24, 2022 (as amended on April 26, 2022, July 6, 2022 and August 12, 2022, and as it may be further amended or supplemented from time to time, the “Merger Agreement”), by and among Delwinds, DWIN Merger Sub Inc., a Delaware corporation and wholly-owned subsidiary of Delwinds (“Merger Sub”), DIAC Sponsor LLC, a Delaware limited liability company (the “Sponsor”), in the capacity as Purchaser Representative for the purposes set forth in the Merger Agreement, and FOXO Technologies Inc., a Delaware corporation (“FOXO”), and approve the transactions contemplated thereby, including the merger of Merger Sub with and into FOXO, with FOXO continuing as the surviving corporation and as a wholly-owned subsidiary of Delwinds, and the issuance of Delwinds securities as merger consideration thereunder, as described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus (the “Merger” and, together with the other transactions contemplated by the Merger Agreement, the “Business Combination”).

The Business Combination Proposal is described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “The Business Combination Proposal (Proposal 2).” A copy of the Merger Agreement is attached to the accompanying joint proxy statement/consent solicitation statement/prospectus as Annex A.

(iii)   The Charter Proposal (Proposal 3) — To consider and vote upon a proposal to approve, in connection with the Business Combination, the replacement of the Current Charter with the proposed new certificate of incorporation of Delwinds (the “Proposed Charter”) in the form attached to the accompanying joint proxy statement/consent solicitation statement/prospectus as Annex B. The Charter Proposal is conditioned on the approval of the Business Combination Proposal. Therefore, if the Business Combination Proposal is not approved, then the Charter Proposal will have no effect, even if approved by Delwinds stockholders. The Charter Proposal is described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “The Charter Proposal (Proposal 3).”

(iv)   Advisory Charter Proposals (Proposals 4 – 7) — To consider and vote, on an advisory and non-binding basis, on four separate Proposals to approve certain governance provisions in the Proposed Charter. These separate votes are not otherwise required by Delaware law, separate and apart from the Charter Proposal, but are required by SEC guidance requiring that stockholders have the opportunity to present their views on important corporate governance provisions. The Business Combination is not conditioned on the separate approval of the Advisory Charter Proposals (separate and apart from approval of the Charter Proposal). The Advisory Charter Proposals are described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “The Advisory Charter Proposals (Proposals 4 – 7).”

(v)    Incentive Plan Proposal (Proposal 8) — To consider and vote upon a proposal to adopt the 2022 Equity Incentive Plan (the “Incentive Plan”), a copy of which is attached to the joint proxy statement/consent solicitation statement/prospectus as Annex D. The Delwinds Board intends to adopt the Incentive Plan, subject to the approval of the stockholders of Delwinds, effective immediately prior to the Closing, to be available to the Combined Company after the Closing. The Incentive Plan Proposal is described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “The Incentive Plan Proposal (Proposal 8).”

(vi)   Management Contingent Share Plan Proposal (Proposal 9) — To consider and vote upon a proposal to adopt an earnout incentive plan following the Closing (the “Management Contingent Share Plan”), a copy of which is attached to the accompanying joint proxy statement/consent solicitation statement/prospectus as Annex E. The Delwinds Board intends to adopt the Management Contingent Share Plan, subject to the approval of the Delwinds stockholders, effective immediately prior to the Closing, which will contain the terms and conditions applicable to shares of Class A Common Stock issued thereunder (the “Management Contingent Shares”) after the Closing. The Management Contingent Share Plan Proposal is described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “The Management Contingent Share Plan Proposal (Proposal 9).”

(vii)  Insider Letter Amendment Proposal (Proposal 10) — To consider and vote upon a proposal to adopt an amendment, effective at the Closing, to reduce the lock-up period applicable to the shares of Delwinds Class A common stock held by the Sponsor set forth in the letter agreement, dated December 10, 2020, by and among Delwinds, the Sponsor and directors and officers of Delwinds (the “Insider Letter”), from one year to six months following the consummation of the Business Combination. A copy of the Insider Letter Amendment is attached to the accompanying joint proxy statement/consent solicitation statement/prospectus as Annex F and is described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “Insider Letter Amendment Proposal (Proposal 10).”

(viii) The NYSE Proposal (Proposal 11) — To consider and vote upon, for purposes of complying with the applicable listing rules of the New York Stock Exchange (the “NYSE”), the issuance of more than 20% of Delwinds common stock in connection with the Business Combination, the Support Subscription Agreements and the Cantor Agreement. The NYSE Proposal is described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “NYSE Proposal (Proposal 11).”

(ix)   The Director Election Proposal (Proposal 12) — To consider and vote upon the election of four (4) directors, who, upon consummation of the Business Combination, will constitute all the members of the board of directors of the Combined Company. The Director Election Proposal is described in more detail in the accompanying joint proxy statement/consent solicitation statement/prospectus under the heading “The Director Election Proposal (Proposal 12).”

(x)    The Adjournment Proposal (Proposal 13) — To consider and vote upon a proposal to adjourn the Delwinds Special Meeting to a later date or dates, if necessary, at the determination of the Delwinds Board. We refer to this proposal as the “Adjournment Proposal” and, together with the NTA Proposal, the Business Combination Proposal, the Charter Proposal, the Advisory Charter Proposals, the Incentive Plan Proposal, the Management Contingent Share Plan Proposal, the Insider Letter Amendment Proposal, the NYSE Proposal and the Director Election Proposal, the “Proposals.”

Only holders of record of Delwinds common stock at the close of business on August 19, 2022 (the “Record Date”) are entitled to notice of the Delwinds Special Meeting and to vote at the Delwinds Special Meeting and any adjournments or postponements of the Delwinds Special Meeting. A complete list of Delwinds stockholders of record entitled to vote at the Delwinds Special Meeting will be available for ten days before the Delwinds Special Meeting at the principal executive offices of Delwinds for inspection by stockholders during ordinary business hours for any purpose germane to the Delwinds Special Meeting.

Pursuant to the Current Charter, in connection with the Business Combination, Delwinds public stockholders may elect to have Delwinds redeem, effective upon the closing of the Business Combination, shares of Delwinds Class A common stock then held by them for cash equal to a pro rata portion of the aggregate amount on deposit in the Trust Account as of two business days prior to the consummation of the Business Combination, including interest earned on the funds held in the Trust Account and not previously released to Delwinds to pay its taxes, divided by the number of then outstanding public shares, subject to the limitations described herein. As of August 19, 2022, based on funds in the Trust Account of approximately $111.9 million as of such date, the pro rata portion of the funds available in the Trust Account for the redemption of public shares of Delwinds Class A common stock was approximately $10.12 per share. Delwinds public stockholders are not required to attend or vote at the Delwinds Special Meeting in order to elect to have Delwinds redeem their shares of Delwinds Class A common stock for cash. This means that public stockholders who hold shares of Delwinds Class A common stock on or before [      ], 2022 (two (2) business days before the Delwinds Special Meeting) will be eligible to elect to have their shares of Delwinds Class A common stock redeemed for cash in connection with the Delwinds Special Meeting, whether or not they are holders as of the Record Date, and whether or not such shares are voted at the Delwinds Special Meeting. A public stockholder, together with any of such stockholder’s affiliates or any other person with whom such public stockholder is acting in concert or as a “group” (as defined under Section 13 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”)), will be restricted from electing to have shares redeemed if, in the aggregate such stockholder’s shares or, if part of such a group, the group’s shares, with respect to 15% or more of the shares of Delwinds common stock included in the units of Delwinds sold in the Delwinds initial public offering (the “IPO”) (including overallotment securities sold to Delwinds’ underwriters in connection with the IPO). Holders of Delwinds’ outstanding public warrants and units do not have redemption rights with respect to such securities in connection with the Business Combination. Holders of outstanding Delwinds units must separate the underlying shares of Delwinds Class A common stock and public warrants prior to exercising redemption rights with respect to the public Delwinds Class A common stock.

Delwinds’ sponsor, DIAC Sponsor LLC, a Delaware limited liability company (the “Sponsor”), and Delwinds’ officers and directors have agreed to waive their redemption rights with respect to any shares of Delwinds Class A common stock they may hold in connection with the consummation of the Business Combination, and such shares will be excluded from the pro rata calculation used to determine the per-share redemption price. Currently, the Sponsor and Delwinds’ officers and directors beneficially own 33.9% of the issued and outstanding shares of Delwinds Class A common stock, giving effect to the conversion from Delwinds Class B common stock immediately prior to the Effective Time at a one to one conversion ratio. The Sponsor and Delwinds’ officers and directors have agreed to vote any shares of Delwinds Class A common stock owned by them on the Record Date in favor of the Business Combination and the other Proposals.

Stockholders should be aware that, effective as of June 8, 2022, RBC Capital Markets, LLC (“RBCCM”) has resigned from its role as Delwinds’ financial advisor and capital markets advisor, and has informed Delwinds that RBCCM waives the deferred portion of the underwriting fees to which RBCCM would otherwise have been entitled in connection with the Business Combination under the Underwriting Agreement dated December 10, 2020, entered into at the time of Delwinds’ initial public offering by Delwinds and its IPO Underwriters, including RBCCM. Stockholders should also be aware that, effective June 16, 2022, Deutsche Bank Securities Inc. (“DB”) has resigned from its roles as financial advisor to FOXO in connection with the Business Combination. Each of RBCCM and DB has disclaimed any responsibility for any portion of this joint proxy statement/consent solicitation/prospectus. Consummation of the Business Combination is not contingent upon the services previously provided by RBCCM or DB to Delwinds or FOXO, respectively, and neither Delwinds nor FOXO expects to replace RBCCM or DB, respectively, as financial advisors or capital markets advisors, prior to the expected Closing. For additional information about RBCCM and DB’s resignations and waivers, as applicable, see “Summary — Recent Developments.”

Your vote is very important, regardless of the number of shares of Delwinds Class A common stock that you own. The approval of the NTA Proposal requires the affirmative vote of holders of sixty-five percent (65%) of the issued and outstanding shares of Delwinds common stock as of the Record Date, and the approval of the Charter Proposal requires the affirmative vote of holders of a majority of the issued and outstanding shares of Delwinds common stock as of the Record Date. Approval of the Business Combination Proposal, the Incentive Plan Proposal, the Management Contingent Share Plan Proposal, the Insider Letter Amendment Proposal and the NYSE Proposal each requires the affirmative vote of the holders of a majority of the shares of Delwinds common stock cast by the stockholders represented in person online or by proxy and entitled to vote thereon at the Delwinds Special Meeting. If the Business Combination Proposal is not approved, the Charter Proposal, the Incentive Plan Proposal, the Management Contingent Share Plan Proposal, the Insider Letter Amendment Proposal and the NYSE Proposal will not be presented to the Delwinds stockholders for a vote. The approval of the Business Combination Proposal, the Charter Proposal, the NYSE Proposal, the Incentive Plan Proposal and the Management Contingent Share Plan Proposal are preconditions to the consummation of the Business Combination. The NTA Proposal is conditioned upon the approval of the Business Combination Proposal. Therefore, if the Business Combination Proposal is not approved, then the NTA Proposal will have no effect, even if approved by Delwinds stockholders. The approval of the Business Combination Proposal and the other Required Proposals are preconditions to the consummation of the Business Combination.

The Delwinds Board formed a special committee comprised entirely of independent and disinterested directors (the “Special Committee”) to consider and negotiate the terms and conditions of the Business Combination and transactions related to the Business Combination and to recommend to the Delwinds Board whether to pursue the Business Combination and, if so, on what terms and conditions.

The Delwinds Board, based in part upon the unanimous recommendation of the Special Committee, has adopted and approved the Merger Agreement and recommends that Delwinds stockholders vote “FOR” all of the proposals presented to Delwinds stockholders at the Delwinds Special Meeting and the election of each of the directors, who, upon consummation of the Business Combination, will constitute all the members of the board of directors of the Combined Company. In arriving at its recommendations, the Delwinds Board and the Special Committee carefully considered a number of factors described in the accompanying joint proxy statement/consent solicitation statement/prospectus. When you consider the recommendation of the Special Committee and the Delwinds Board, you should keep in mind that directors and officers of Delwinds have interests in the Business Combination that may conflict with your interests as a stockholder. For instance, rather than liquidating Delwinds, the Sponsor will benefit from the Business Combination and may be incentivized to complete the Business Combination, even if the transaction is unfavorable to stockholders. See the section entitled “The Business Combination Proposal — Certain Interests of Delwinds’ Directors and Officers and Others in the Business Combination” for a further discussion of these considerations.

All Delwinds stockholders are cordially invited to attend the Delwinds Special Meeting and we are providing the accompanying joint proxy statement/consent solicitation statement/prospectus and proxy card in connection with the solicitation of proxies to be voted at the Delwinds Special Meeting (or any adjournment or postponement thereof). To ensure your representation at the Delwinds Special Meeting, however, you are urged to complete, sign, date and return the enclosed proxy card as soon as possible. If your shares are held in an account at a brokerage firm, bank or other nominee, you must instruct your broker, bank or other nominee on how to vote your shares or, if you wish to attend the Delwinds Special Meeting and vote, obtain a proxy from your broker, bank or other nominee.

Your vote is important regardless of the number of shares you own. Whether you plan to attend the Delwinds Special Meeting or not, please sign, date and return the enclosed proxy card as soon as possible in the envelope provided. If your shares are held in “street name” or are in a margin or similar account, you should contact your broker to ensure that votes related to the shares you beneficially own are properly counted.

Your attention is directed to the joint proxy statement/consent solicitation statement/prospectus accompanying this notice (including the annexes thereto) for a more complete description of the proposed Business Combination and related transactions and each of the Proposals. We encourage you to read this joint proxy statement/consent solicitation statement/prospectus carefully. If you have any questions or need assistance voting your shares, please call us at (713) 337-4077.

IF YOU RETURN YOUR PROXY CARD WITHOUT AN INDICATION OF HOW YOU WISH TO VOTE, YOUR SHARES WILL BE VOTED IN FAVOR OF EACH OF THE PROPOSALS.

TO EXERCISE YOUR REDEMPTION RIGHTS, YOU MUST (1) IF YOU HOLD SHARES OF DELWINDS CLASS A COMMON STOCK THROUGH UNITS, ELECT TO SEPARATE YOUR UNITS INTO THE UNDERLYING SHARES OF DELWINDS CLASS A COMMON STOCK AND PUBLIC WARRANTS PRIOR TO EXERCISING YOUR REDEMPTION RIGHTS WITH RESPECT TO THE PUBLIC SHARES, (2) SUBMIT A WRITTEN REQUEST, INCLUDING THE LEGAL NAME, PHONE NUMBER AND ADDRESS OF THE BENEFICIAL OWNER OF THE SHARES FOR WHICH REDEMPTION IS REQUESTED, TO THE TRANSFER AGENT AT LEAST TWO BUSINESS DAYS PRIOR TO THE VOTE AT THE DELWINDS SPECIAL MEETING, THAT YOUR PUBLIC SHARES BE REDEEMED FOR CASH AND (3) DELIVER YOUR STOCK CERTIFICATES (IF ANY) AND OTHER REDEMPTION FORMS TO THE TRANSFER AGENT, PHYSICALLY OR ELECTRONICALLY USING THE DEPOSITORY TRUST COMPANY’S DWAC (DEPOSIT/WITHDRAWAL AT CUSTODIAN) SYSTEM, IN EACH CASE, IN ACCORDANCE WITH THE PROCEDURES AND DEADLINES DESCRIBED IN THE JOINT PROXY STATEMENT/CONSENT SOLICITATION STATEMENT/PROSPECTUS. IF THE BUSINESS COMBINATION IS NOT CONSUMMATED, THEN THE PUBLIC SHARES WILL NOT BE REDEEMED FOR CASH. IF YOU HOLD THE SHARES IN STREET NAME, YOU WILL NEED TO INSTRUCT THE ACCOUNT EXECUTIVE AT YOUR BANK, BROKER OR OTHER NOMINEE TO WITHDRAW THE SHARES FROM YOUR ACCOUNT IN ORDER TO EXERCISE YOUR REDEMPTION RIGHTS. SEE “THE DELWINDS SPECIAL MEETING — REDEMPTION RIGHTS’’ IN THIS JOINT PROXY STATEMENT/CONSENT SOLICITATION STATEMENT/PROSPECTUS FOR MORE SPECIFIC INSTRUCTIONS.

ABOUT THIS DOCUMENT

This document, which forms part of a registration statement on Form S-4 filed with the SEC by Delwinds, constitutes a prospectus of Delwinds under the Securities Act of 1933, as amended (the “Securities Act”), with respect to the shares of common stock of Delwinds to be issued to FOXO securityholders under the Merger Agreement. This document also constitutes a consent solicitation statement of FOXO with respect to the solicitation of the consent of FOXO stockholders in connection with the Merger Agreement. This document also constitutes a notice of a meeting and a proxy statement of Delwinds under Section 14(a) of the Exchange Act with respect to the Delwinds Special Meeting at which Delwinds stockholders will be asked to consider and vote on a proposal to approve the Business Combination by the approval and adoption of the Merger Agreement, among other matters.

You should rely only on the information contained or incorporated by reference into this joint proxy statement/consent solicitation statement/prospectus. No one has been authorized to provide you with information that is different from that contained in, or incorporated by reference into, this joint proxy statement/consent solicitation statement/prospectus. This joint proxy statement/consent solicitation statement/prospectus is dated as of the date set forth on the cover hereof. You should not assume that the information contained in this joint proxy statement/consent solicitation statement/prospectus is accurate as of any date other than that date on the cover hereof, or the date referenced herein, as applicable. You should not assume that the information incorporated by reference into this joint proxy statement/consent solicitation statement/prospectus is accurate as of any date other than the date of such incorporated document. Neither the mailing of this joint proxy statement/consent solicitation statement/prospectus to Delwinds stockholders nor the issuance by Delwinds of its securities in connection with the Business Combination will create any implication to the contrary.

Information contained in this joint proxy statement/consent solicitation statement/prospectus regarding Delwinds and its business, operations, management and other matters has been provided by Delwinds and its representatives and information contained in this joint proxy statement/consent solicitation statement/prospectus regarding FOXO and its business, operations, management and other matters has been provided by FOXO and its representatives.

This joint proxy statement/consent solicitation statement/prospectus does not constitute an offer to sell or a solicitation of an offer to buy any securities, or the solicitation of a proxy or consent, in any jurisdiction to or from any person to whom it is unlawful to make any such offer or solicitation in such jurisdiction.

If you would like additional copies of this joint proxy statement/consent solicitation statement/prospectus or if you have questions about the Business Combination or the proposals to be presented at the Delwinds Special Meeting, please contact Delwinds’ proxy solicitor listed below. You will not be charged for any of the documents that you request.

Saratoga Proxy Consulting, at:
Joe Mills/John Ferguson
Saratoga Proxy Consulting LLC
520 Eighth Ave, 14th Floor
New York, NY 10018
(888) 368-0379
info@saratogaproxy.com

In order for you to receive timely delivery of the documents in advance of the Delwinds Special Meeting to be held on [            ], 2022, you must request the information by [            ], 2022.

For a more detailed description of the information incorporated by reference in this joint proxy statement/consent solicitation statement/prospectus and how you may obtain it, see the section captioned “Where You Can Find More Information” beginning on page 290 of this joint proxy statement/consent solicitation statement/prospectus.

TABLE OF CONTENTS

TRADEMARKS

FOXO owns or has rights to trademarks that it uses in connection with the operation of its businesses and that are used in this joint proxy statement/consent solicitation statement/prospectus. This joint proxy statement/consent solicitation statement/prospectus includes trademarks of FOXO such as “FOXO Technologies,” “FOXO Life,” “FOXO Labs,” “FOXO Life Insurance Company,” “Life Insurance Designed to Keep You Alive,” “Longevity Report,” and others, which are protected under applicable intellectual property laws and are the property of FOXO or its subsidiaries. This joint proxy statement/consent solicitation statement/prospectus also includes other trademarks, trade names and service marks that are the property of their respective owners. Solely for convenience, in some cases, the trademarks, trade names and service marks referred to in this joint proxy statement/consent solicitation statement/prospectus are listed without the applicable®, ™ and SM symbols, but they will assert, to the fullest extent under applicable law, their rights to these trademarks, trade names and service marks.

MARKET AND INDUSTRY DATA

This joint proxy statement/consent solicitation statement/prospectus includes industry position and industry data, forecasts, market size and growth and other data that Delwinds and FOXO obtained or derived from internal company reports, independent third-party publications, surveys and studies by third parties and other industry data. Some data are also based on good faith estimates, which are derived from internal company research or analyses or review of internal company reports as well as the independent sources referred to above. Although both Delwinds and FOXO believe that the information on which the companies have based these estimates of industry position and industry data are generally reliable, the accuracy and completeness of this information is not guaranteed and they have not independently verified any of the data from third-party sources nor have they ascertained the underlying economic assumptions relied upon therein. Delwinds’ and FOXO’s internal company reports have not been verified by any independent source. Statements as to industry position are based on market data currently available. Among other items, certain of the market research included in this joint proxy statement/consent solicitation statement/prospectus was published prior to the COVID-19 pandemic and did not anticipate the virus or the impact it has caused on Delwinds’ and FOXO’s industries. Delwinds and FOXO have utilized this pre-pandemic market research in the absence of updated sources. While Delwinds and FOXO are not aware of any misstatements regarding the industry data presented herein, these estimates involve risks and uncertainties and are subject to change based on various factors, including those discussed under the heading “Risk Factors” in this joint proxy statement/consent solicitation statement/prospectus.

FREQUENTLY USED TERMS

Unless otherwise stated or unless the context otherwise requires, the terms “we,” “us,” “our,” and “Delwinds” refer to Delwinds Insurance Acquisition Corp., and if the context requires, to the Combined Company following consummation of the Business Combination, which will be renamed “FOXO Technologies Inc.”

In this document:

“2021 Bridge Agreements” means, collectively, the stock purchase agreement, 2021 Bridge Debentures, 2021 Bridge Warrants, lock-up agreements and other agreements between FOXO and the 2021 Bridge Investors, as amended by the 2021 Bridge Amendment, as such agreements may be amended, modified or supplemented.

“2021 Bridge Amendment” means the contingent amendment agreement, effective as of February 22, 2022, amending the 2021 Bridge Agreements.

“2021 Bridge Debentures” means the 12.5% Original Issue Discount Convertible Debentures, as may be amended, modified or supplemented from time to time in accordance with their terms, issued by FOXO between January 2021 and March 2021.

“2021 Bridge Investors” means all of the purchasers of the 2021 Bridge Debentures.

“2021 Bridge Warrants” means the warrants to purchase FOXO Class A common stock, as may be amended, modified or supplemented from time to time in accordance with their terms, issued by FOXO to the 2021 Bridge Investors and the placement agent, or its designees, in connection with such offering.

“2022 Bridge Agreements” means, collectively, the stock purchase agreements, debentures and other agreements between FOXO and the purchasers of the 2022 Bridge Debentures, as such agreements may be amended, modified or supplemented.

“2022 Bridge Debentures” means the 10% Original Issue Discount Convertible Debentures, as may be amended, modified or supplemented from time to time in accordance with their terms, issued by FOXO between February 2022 and the 2022 Bridge Financing End Date.

“2022 Bridge Financing End Date” means the earlier of (i) the termination of the offering of the 2022 Bridge Debentures as determined by FOXO and (ii) the Outside Date.

“2022 Bridge Investors” means all of the purchasers of the 2022 Bridge Debentures.

“AAA” means the American Arbitration Association or any successor entity conducting arbitrations.

“Administrative Services Agreement” means the agreement, dated December 10, 2020, between Delwinds and the Sponsor pursuant to which Delwinds pays the Sponsor a total of $10,000 per month for office space, utilities and secretarial support, as may be amended, modified or supplemented.

“Ancillary Documents” means each agreement, instrument or document attached to the Merger Agreement or executed or delivered by any party to the Merger Agreement in connection with or pursuant to the Merger Agreement.

“Arkansas Insurance Department” means the Arkansas Insurance Department, created by the State of Arkansas.

“Assumed Options” means the Options to purchase shares of Class A Common Stock that, as of the Closing, shall be issued to holders of FOXO Options outstanding and unexercised immediately prior to the Effective Time.

“Assumed Warrants” means the Warrants to purchase shares of Class A Common Stock that, as of the Closing, shall be issued to holders of FOXO Warrants outstanding and unexercised immediately prior to the Effective Time.

“August Order” means the Revised Order entered into by the Arkansas Insurance Department in connection with a hearing held at the Arkansas Insurance Department on August 10, 2021, related to the acquisition of control of Memorial Insurance Company of America by FOXO Life Insurance Company.

“Bridge Investor Side Letter” means the letter agreement between FOXO and an institutional investor in FOXO’s offering of the 2022 Bridge Debentures, pursuant to which FOXO agreed to issue to such investor either (i) if in connection with the Closing, such number of shares of FOXO Common Stock, to be issued to such investor immediately prior to the Effective Date, that will be exchangeable for 350,000 shares of Class A Common Stock or (ii) if such investor’s 2022 Bridge Debenture is required to be earlier repaid in full or in connection with the consummation of a Qualified Offering (as defined in the 2022 Bridge Debentures) other than a transaction with a special purpose acquisition company, 350,000 shares of FOXO Common Stock, in each case, subject to adjustment for any prepayments.

“Business Combination” means the proposed business combination of Delwinds and FOXO pursuant to the terms of the Merger Agreement and the other transactions contemplated by the Merger Agreement.

“Cantor” means Cantor Fitzgerald & Co.

“Cantor Agreement” means the Common Stock Purchase Agreement, dated as of February 24, 2022, as may be amended, modified or supplemented.

“Cantor Commitment Fee” means the fee payable to Cantor on or prior to the Closing as consideration for its irrevocable commitment to purchase shares of Class A Common Stock upon the terms and conditions set forth in the Cantor Agreement. The Cantor Commitment Fee is payable by the issuance of a number of shares of Class A Common Stock equal to the quotient obtained by dividing (i) $1,600,000 by (ii) the closing price of Class A Common Stock on the trading day immediately preceding the date of delivery thereof.

“Cantor Commitment Shares” means shares of Class A Common Stock representing the Cantor Commitment Fee.

“Cantor Investor” means CF Principal Investments LLC, an affiliate of Cantor.

“Cantor RRA” means the Registration Rights Agreement dated as of February 24, 2022, between Delwinds and the Cantor Investor, pursuant to which Cantor Investor will have certain registration rights in connection with securities issued pursuant to the Cantor Agreement, as may be amended, modified or supplemented.

“CCM” means J.V.B. Financial Group, LLC, acting through its Cohen & Company Capital Markets division.

“CCM Engagement Letter” means the engagement letter between Delwinds and CCM, dated as of October 21, 2021.

“Class A Common Stock” means the shares of Class A common stock, par value $0.0001 per share, of the Combined Company.

“Class V Common Stock” means the shares of Class V common stock of the Combined Company which were to be entitled to ten (10) votes per share on all matters to be voted on by the holders of Common Stock after the Closing into which shares of FOXO Class B common stock were to be converted pursuant to the Merger, but which class of Common Stock has been eliminated under Amendment No. 3 to the Merger Agreement, dated August    , 2022.

“Closing” means the closing of the Business Combination.

“Closing Date” means the date of the Closing of the Business Combination.

“Closing Indebtedness” means the aggregate amount of indebtedness of the Target Companies as of the Reference Time on a consolidated basis determined in accordance with the accounting principles as defined in the Merger Agreement.

“Closing Statement” means the statement, to be delivered by FOXO to Delwinds three Business Days prior to the Closing Date, certified by FOXO’s Chief Executive Officer, setting forth FOXO’s calculation of Closing Indebtedness and Transaction Expenses as of the Reference Time.

“Code” means the Internal Revenue Code of 1986, as amended.

“Combined Company” refers to FOXO Technologies Inc. (which will be the new name of Delwinds after the Business Combination, and which will include FOXO and any other direct or indirect subsidiaries of FOXO, to the extent applicable).

“Combined Company Board” refers to the board of directors of the Combined Company.

“Common Stock” means the Class A Common Stock.

“Company Convertible Securities” means, collectively, each outstanding option, warrant, convertible note or other right to subscribe or purchase any capital stock of FOXO or securities convertible into or exchangeable for, or that otherwise confer on the holder any right to acquire any capital stock of FOXO.

“Company Convertible Debt” means the outstanding obligations of FOXO as of the Closing under the Company Convertible Debt Agreements.

“Company Convertible Debt Agreements” means the 2021 Bridge Agreements and the 2022 Bridge Agreements.

“Company Preferred Stock and Convertible Debt Exchange” means the mandatory exchange or conversion of all of the issued and outstanding shares of Company Preferred Stock and Company Convertible Debt for shares of FOXO Common Stock at the applicable conversion ratio (including any accrued or declared but unpaid dividends or interest) as set forth in the FOXO Charter and/or applicable Company Convertible Debt Agreements prior to and as a condition to the Closing.

“Conversion Ratio” means the Per Share Price divided by the Redemption Price, as such ratio will be determined as of the Closing Date.

“COVID-19 pandemic” means the SARS-CoV-2 pandemic.

“Current Charter” means Delwinds’ certificate of incorporation filed with the Secretary of State of the State of Delaware on April 27, 2020, as amended on (i) December 10, 2020 and (ii) June 6, 2022.

“Delwinds” means Delwinds Insurance Acquisition Corp., a Delaware corporation, which will be renamed “FOXO Technologies Inc.” following consummation of the Closing.

“Delwinds Board” means the board of directors of Delwinds prior to the Business Combination.

“Delwinds Class A common stock” means the Class A common stock, par value $0.0001, of Delwinds, prior to the Business Combination.

“Delwinds Class B common stock” means the Class B common stock, par value $0.0001, of Delwinds, prior to the Business Combination.

“Delwinds common stock” means the Class A common stock and the Class B common stock of Delwinds.

“Delwinds Preferred Stock” means the preferred stock, par value $0.0001 per share, of Delwinds, prior to the Business Combination.

“Delwinds Special Meeting” means the special meeting of the stockholders of Delwinds, to be held virtually at [•] [•], Eastern Time on [____], 2022.

“Delwinds Securities” means the Units, the Delwinds common stock, the Delwinds Preferred Stock and the Warrants, collectively.

“DB” means Deutsche Bank Securities Inc., financial advisor to FOXO.

“DGCL” means the General Corporation Law of the State of Delaware, as amended.

“DWAC” means The Depository Trust Company’s deposit withdrawal at custodian.

“Effective Time” means the effective time of the Merger in accordance with the Merger Agreement.

“Employment Agreements” means the executive employment agreements between Delwinds and certain FOXO executives to be entered into and delivered to Delwinds prior to and as a condition to the Closing, as may be amended, modified or supplemented.

“Excess Transaction Expenses” means any Transaction Expenses of FOXO, as determined as of the Reference Time, in excess of $7,500,000.

“Exchange Act” means Securities Exchange Act of 1934, as amended.

“Exchange Agent” means Continental Stock Transfer & Trust Company, or another agent appointed by Delwinds and reasonably acceptable to FOXO for the purposes and to perform the actions and transactions described in the Merger Agreement in connection with the Closing.

“Extension Loan” means the non-interest bearing loan from FOXO to Delwinds in the aggregate principal amount of up to $1,159,995.69.

“Financing Agreements” means the Support Subscription Agreements and any other financing agreements as may be entered into during the Interim Period in accordance with the terms of the Merger Agreement.

“Form A Filing” means the Form A Statement Regarding the Acquisition of Control of a Domestic Insurer required to be made with the Arkansas Insurance Commissioner for approval of Delwinds’ acquisition of control of FOXO Life Insurance Company.

“Founder Shares” means Delwinds Class B common stock initially purchased by the Sponsor in the Private Placement prior to the IPO, and the shares of Delwinds Class A common stock issued upon the conversion thereof in accordance with the terms of the Current Charter.

“FOXO” means FOXO Technologies Inc., a Delaware corporation, prior to the Business Combination. References herein to FOXO will include its subsidiaries to the extent reasonably applicable.

“FOXO Board” means the board of directors of FOXO.

“FOXO Common Stock” means, collectively, the FOXO Class A common stock and FOXO Class B common stock.

“FOXO Class A common stock” means shares prior to the Business Combination of Class A common stock, par value $0.00001 per share, of FOXO.

“FOXO Class B common stock” means shares prior to the Business Combination of Class B common stock, par value $0.00001 per share, of FOXO.

“FOXO Equity Plan” means the FOXO Technologies Inc. 2020 Equity Incentive Plan.

“FOXO Insurance Authorizations” means all permits, consents, orders or other approvals or authorizations required for FOXO Life Insurance Company to conduct or operate its business as an insurance company, including, without limitation, authorization to underwrite life insurance policies in compliance with terms of the FOXO Insurance License and requirements of the Arkansas Insurance Department.

“FOXO Options” means options to purchase FOXO Class A common stock.

“FOXO Preferred Stock” means shares of preferred stock, par value $0.00001 per share, of FOXO.

“FOXO Stockholders” refers to holders of capital stock of FOXO as of the time immediately prior to the Effective Time.

“FOXO Warrants” means warrants to purchase FOXO Class A common stock.

“Fully-Diluted Company Shares” means the total number of issued and outstanding shares of FOXO Common Stock (a) after giving effect to the Company Preferred and Convertible Debt Exchange immediately prior to the Effective Time and (b) treating all Company Convertible Securities as fully vested and as if the Company Convertible Securities had been exercised as of the Effective Time (other than treasury shares).

“Grant Thornton” means Grant Thornton LLP, Delwinds’ independent registered public accounting firm.

“HSR Act” means the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended.

“Incentive Plan” means the 2022 Equity Incentive Plan of the Combined Company, a copy of which is attached to this joint proxy statement/consent solicitation statement/prospectus as Annex D.

“Insider Letter” means the letter agreement dated December 10, 2020, by and among Delwinds, its officers and directors and the Sponsor pursuant to which, among other things, the parties thereto agreed to vote all of the Delwinds shares held by them in favor of any business combination presented to them and not to redeem any Public Shares held by them in connection therewith.

“Insider Letter Amendment” means the proposed amendment to the Insider Letter the purpose of which is to shorten the period of time after the Closing during which the Founder Shares are subject to certain transfer restrictions thereunder to a period of six months, subject to approval by the Public Stockholders and consent of the IPO Underwriters.

“Initial stockholders” means the Sponsor and any other holders of Delwinds’ Founder Shares prior to the IPO (or their permitted transferees).

“Interim Period” means the period of time between the date of execution of the Merger Agreement and the Closing Date.

“IPO” means Delwinds’ initial public offering that was consummated by Delwinds on December 11, 2020.

“IPO Prospectus” means the final prospectus of Delwinds, dated December 10, 2020, in connection with the IPO, as filed with the SEC pursuant to Rule 424(b) under the Securities Act on December 11, 2020 (File No. 333-248753).

“IPO Underwriters” means Cantor Fitzgerald & Co. and RBC Capital Markets, LLC.

“Lock-Up Agreements” means the lock-up agreements entered into concurrent with the execution of the Merger Agreement pursuant to which certain holders of shares of FOXO Stock agreed to certain transfer and other restrictions for a period of time after the Closing, as set forth in such agreements, as may be amended, modified or supplemented.

“KPMG” means KPMG LLP, FOXO’s independent registered public accounting firm.

“Management Contingent Shares” means the 9,200,000 restricted shares of Class A Common Stock to be issued at the Closing pursuant to the terms of the Management Contingent Share Plan, which shall, after the Closing, be subject to the vesting and forfeiture restrictions comprising the Management Contingent Share Terms.

“Management Contingent Share Terms” means the vesting and forfeiture conditions applicable to the Management Contingent Shares pursuant to the terms of the Management Contingent Share Plan.

“Merger” means the merger of Merger Sub with and into FOXO, with FOXO continuing as the surviving corporation and as a wholly-owned subsidiary of Delwinds, in accordance with the terms of the Merger Agreement.

“Merger Agreement” means the Agreement and Plan of Merger, dated February 24, 2022, as amended on April 26, 2022, July 6, 2022 and August 12, 2022, and as it may be further amended or supplemented from time to time, by and among Delwinds, Merger Sub, Sponsor, as purchaser representative, and FOXO.

“Merger Consideration” means the number of Delwinds securities with an aggregate value equal to (a) Three Hundred Million U.S. Dollars ($300,000,000), minus (b) the amount of Closing Indebtedness (excluding, for the avoidance of doubt, Company Convertible Debt converted into shares of the Company Class A Common Stock in accordance with the Company Preferred Stock and Convertible Debt Exchange), minus (c) the amount of any Excess Transaction Expenses, minus (d) the amount equal to the Management Contingent Shares multiplied by the Redemption Price.

“Merger Sub” means DWIN Merger Sub Inc., a Delaware corporation and wholly-owned subsidiary of Delwinds.

“Non-Competition Agreements” means the agreements entered into by certain executives of FOXO concurrent with the terms of the Merger Agreement pursuant to which the individuals party thereto agreed to certain non-competition and non-solicitation covenants as set forth in such agreements, as may be amended, modified or supplemented.

“NYSE” means the New York Stock Exchange.

“Original Outside Date” means July 24, 2022, the five (5) month anniversary of the date of execution of the Merger Agreement.

“Organizational Documents” means with respect to any Person that is an entity, its certificate of incorporation or formation, bylaws, operating agreement, memorandum and articles of association or similar organizational documents, in each case, as amended.

“Outside Date” means the Original Outside Date, as such date may be extended in accordance with the terms of the Merger Agreement, as of which date either Delwinds or FOXO may terminate the Merger Agreement if any of the conditions to the closing have not been satisfied or waived.

“Per Share Price” means the amount equal to the Merger Consideration divided by the Fully-Diluted Company Shares.

“Private Placement” means the private placement consummated simultaneously with the IPO in which Delwinds issued the Private Units to the Sponsor.

“Proposals” means the NTA Proposal, the Business Combination Proposal, the Charter Proposal, the Advisory Charter Proposals, the Incentive Plan Proposal, the Management Contingent Share Plan Proposal, the Insider Letter Amendment Proposal, the NYSE Proposal, the Director Election Proposal and the Adjournment Proposal.

“Proposed Charter” means the second amended and restated certificate of incorporation of Delwinds in the form included as Annex B to this joint proxy statement/consent solicitation statement/prospectus, to be adopted by Delwinds pursuant to the Charter Proposal.

“Proposed Bylaws” means the amended and restated bylaws of Combined Company in the form included as Annex C to this joint proxy statement/consent solicitation statement/prospectus, to be adopted by Delwinds upon consummation of the Business Combination.

“Private Units” means the units issued by Delwinds in a private placement to the Sponsor at the time of the consummation of the IPO consisting of one (1) share of Delwinds Class A common stock and one-half (½) of one Private Warrant.

“Private Warrants” means one (1) whole warrant that was included in as part of each Private Unit, entitling the holder thereof to purchase one (1) share of Delwinds Class A common stock at a purchase price of $11.50 per share.

“Public Shares” means Delwinds Class A common stock underlying the Units sold in the IPO, including any overallotment securities acquired by Delwinds’ underwriters.

“Public Stockholders” means holders of Delwinds Public Shares.

“Public Units” means the units issued in the IPO (including overallotment units acquired by Delwinds’ underwriter) consisting of one (1) share of Delwinds Class A common stock and one-half (½) of one Public Warrant.

“Public Warrant” means one (1) whole redeemable warrant that was included in as part of each Public Unit, entitling the holder thereof to purchase one (1) share of Delwinds Class A common stock at a purchase price of $11.50 per share.

“Purchaser Representative” means the Sponsor, in its capacity as Purchaser Representative from and after the Closing in accordance with the terms of the Merger Agreement.

“RBCCM” means RBC Capital Markets, LLC.

“Redemption” means the right of the holders of Delwinds Class A common stock to have their shares redeemed in accordance with the procedures set forth in this joint proxy statement/consent solicitation statement/prospectus and the Current Charter.

“Redemption Price” means an amount equal to the price at which the Delwinds Class A common stock is redeemed or converted pursuant to the Redemption.

“Reference Time” means the close of business of FOXO as of the Closing Date, without giving effect to the Transactions.

“Regulatory Approvals” means all consents, approvals, applications and filings required to be made with any governmental authority in connection with the consummation of the Business Combination, including the Form A filing and approval by the Arkansas Insurance Department.

“Required Company Stockholder Approval” means the vote of the FOXO Stockholders (including any separate class or series vote that is required pursuant to the FOXO Organizational Documents, any stockholder agreement or otherwise) required to approve the Merger Agreement and each applicable Ancillary Agreement and all of the transactions contemplated by the Merger Agreement in accordance with the FOXO Organizational Documents.

“Required Delwinds Stockholder Approval” means the vote of the Delwinds stockholders required to approve the Merger Agreement and each applicable Ancillary Agreement and all of the transactions contemplated by the Merger Agreement in accordance with the Delwinds Organizational Documents.

“Required Proposals” means the Business Combination Proposal, the Charter Proposal, the Incentive Plan Proposal, the Management Contingent Share Plan Proposal, the Director Election Proposal and the NYSE Proposal.

“SEC” means the U.S. Securities and Exchange Commission.

“Securities Act” means the Securities Act of 1933, as amended.

“Special Committee” means the Special Committee of the Delwinds Board, composed of E. Benjamin Nelson, Paul Britton Newhouse and Ryan Rugg, independent directors of Delwinds.

“Sponsor” means DIAC Sponsor LLC, a Delaware limited liability company.

“Sponsor Shares” means the Founder Shares and the Delwinds Class A common stock underlying the Private Units held by the Sponsor.

“Sponsor February Promissory Note” means the promissory note, issued on February 23, 2022 by Delwinds, in the principal amount of up to $2,000,000, to the Sponsor.

“Stockholder Merger Consideration” means the total portion of the Merger Consideration amount payable to all FOXO Stockholders (but excluding holders of FOXO Options).

“Subscription Investors” means Andrew J. Poole and The Gray Insurance Company, each party to the Support Subscription Agreements executed as of the date of the Merger Agreement.

“Subscription Shares” means the up to 597,813 shares of Class A Common Stock that may be issued to the Subscription Investors at the Closing pursuant and subject to the terms of the Support Subscription Agreements, as adjusted as a result of the RBCCM Resignation.

“Support Subscription Agreements” means the agreements with the Subscription Investors entered into concurrent with the execution of the Merger Agreement.

“Target Companies” means FOXO and each of its direct and indirect subsidiaries.

“Threshold Amount” means $10,000,000, subject to reduction (up to a maximum of $5,000,000) for (i) any agreed upon reduction of the deferred underwriting fee owed to the IPO Underwriters or satisfaction of such obligations by the issuance of shares of Class A Common Stock, in lieu of cash, or (ii) any unsecured convertible debt of the FOXO that is issued by FOXO subject to the terms and conditions specified in the Support Subscription Agreements.

“Transactions” means the Business Combination, including the Merger and all of the transactions contemplated by the Merger Agreement and the Ancillary Agreements.

“Transmittal Documents” means the letters of transmittal and other documents FOXO security holders may be required to complete and provide to FOXO, Delwinds or the Exchange Agent in advance of their receiving consideration from the Transactions in accordance with the terms of the Merger Agreement.

“Transaction Expenses” means all of the fees and expenses of FOXO, including all of its Subsidiaries, incurred or payable at the Closing in connection with the Business Combination.

“Trust Account” means the trust account of Delwinds, established at the time of the IPO, containing the net proceeds of the sale of the Units in the IPO, including from overallotment securities sold by Delwinds’ underwriters, and the sale of Private Units following the closing of the IPO.

“Trust Agreement” means the Investment Management Trust Agreement, dated as of December 10, 2020, as it may be amended, by and between Delwinds and the Trustee, as well as any other agreements entered into related to or governing the Trust Account.

“Trustee” means Continental Stock Transfer & Trust Company, a New York corporation, in its capacity as Trustee under the Trust Agreement.

“UHY” means UHY LLP, FOXO’s 2020 independent registered public accounting firm.

“Underwriting Agreement” means that certain underwriting agreement, dated as of December 10, 2020, by and between Delwinds and the IPO Underwriters.

“Units” means Private Units and Public Units, collectively.

“Voting Agreements” means the Voting and Support Agreement entered into simultaneously with the execution of the Merger Agreement by FOXO and holders of capital stock of FOXO sufficient to approve the Merger and other Transactions (including any required separate class or services votes), as may be amended, modified or supplemented.

“Warrants” means Private Warrants and Public Warrants, collectively.

CAUTIONARY NOTE REGARDING FORWARD-LOOKING STATEMENTS

Certain statements contained in this joint proxy statement/consent solicitation statement/prospectus may constitute “forward-looking statements” within the meaning of the “safe harbor” provisions of the United States Private Securities Litigation Reform Act of 1995. This includes, without limitation, statements regarding the financial position, business strategy and the plans and objectives of management for future operations, including as they relate to the potential Business Combination, of Delwinds. These statements constitute projections, forecasts and forward-looking statements, and are not guarantees of performance. Such statements can be identified by the fact that they do not relate strictly to historical or current facts. When used in this joint proxy statement/consent solicitation statement/prospectus, forward-looking statements may be identified by the use of words such as “estimate,” “continue,” “could,” “may,” “might,” “possible,” “predict,” “should,” “would,” “plan,” “project,” “forecast,” “intend,” “will,” “expect,” “anticipate,” “believe,” “seek,” “target,” “designed to” or other similar expressions that predict or indicate future events or trends or that are not statements of historical facts. In addition, any statements that refer to projections, forecasts or other characterizations of future events or circumstances, including any underlying assumptions, are forward-looking statements.

Delwinds and FOXO caution readers of this joint proxy statement/consent solicitation statement/prospectus that these forward-looking statements are subject to risks and uncertainties, most of which are difficult to predict and many of which are beyond Delwinds’ and FOXO’s control, which could cause the actual results to differ materially from the expected results. These forward-looking statements include, but are not limited to, statements regarding estimates and forecasts of financial and performance metrics, projections of market opportunity and market share, potential benefits and the commercial attractiveness to its customers of FOXO’s products and services, the potential success of FOXO’s marketing and expansion strategies, potential benefits of the Business Combination (including with respect to stockholder value), and expectations related to the terms and timing of the Business Combination. These statements are based on various assumptions, whether or not identified in this joint proxy statement/consent solicitation statement/prospectus, and on the current expectations of FOXO’s and Delwinds’ management and are not predictions of actual performance. These forward-looking statements are provided for illustrative purposes only and are not intended to serve as, and must not be relied on by any investor as, a guarantee, an assurance, a prediction or a definitive statement of fact or probability. Actual events and circumstances are difficult or impossible to predict and will differ from assumptions. These forward-looking statements are subject to a number of risks and uncertainties, including:

•        the size and conditions affecting the markets in which FOXO expects to sell products and services;

•        FOXO’s success in developing epigenetic biomarkers with actuarial significance and acceptance of using those epigenetic biomarkers by life insurance carriers and customers;

•        the success of relationships FOXO expects to establish with insurance carriers and reinsurers;

•        fluctuations in capital spending in the life insurance market;

•        the continued impact of the COVID-19 pandemic on the global economy and financial markets, including any restrictions on FOXO’s operations and the operations of FOXO’s customers and suppliers resulting from public health requirements and government mandates;

•        changes in applicable laws or regulations;

•        the possibility that FOXO’s business or the Combined Company may be adversely affected by other economic business, and/or competitive factors;

•        the risk that current trends in the life insurance product market decelerate or do not continue;

•        estimates for the prospects and financial performance of FOXO’s business may prove to be incorrect or materially different from actual results;

•        the inability of the parties to successfully or timely consummate the proposed Business Combination, including the risk that any insurance or other regulatory approvals are not obtained, are delayed or are subject to unanticipated conditions that could adversely affect the Combined Company or the expected benefits of the proposed Business Combination or that the approval of the stockholders of Delwinds or FOXO is not obtained;

•        failure to realize the anticipated benefits of the proposed Business Combination;

•        risks relating to the uncertainty of accelerated underwriting and changing conditions of the industries in which FOXO expects to operate;

•        risks related to future market adoption of FOXO’s offerings;

•        risks related to FOXO’s marketing and growth strategies;

•        the effects of competition on FOXO’s future business;

•        the amount of redemption requests made by Delwinds’ public stockholders;

•        the ability of Delwinds or the Combined Company to issue equity or equity-linked securities in connection with the proposed Business Combination or in the future;

•        FOXO and Delwinds’ inability to complete the proposed Business Combination as contemplated by the Merger Agreement;

•        matters discovered by the parties as they complete their respective due diligence investigation of the other;

•        the inability to recognize the anticipated benefits of the proposed Business Combination, which may be affected by, among other things, the amount of cash available following any redemptions by Delwinds stockholders;

•        the ability of the Combined Company to meet the initial listing standards of the New York Stock Exchange upon consummation of the Business Combination;

•        costs related to the proposed Business Combination;

•        expectations with respect to future operating and financial performance and growth, including when FOXO will generate positive cash flow from operations;

•        FOXO’s ability to raise funding on reasonable terms as necessary to develop its products in the timeframe contemplated by its business plan;

•        FOXO’s ability to execute its anticipated business plans and strategy;

•        the failure to satisfy the conditions to the consummation of the Business Combination, including the approval of the Business Combination and definitive agreements for the Business Combination by the stockholders of Delwinds;

•        the occurrence of any event, change or other circumstance that could give rise to the termination of the Business Combination;

•        the outcome of any legal proceedings that may be instituted against FOXO or Delwinds related to the Business Combination, and those factors discussed in Delwinds’ IPO Prospectus under the heading “Risk Factors,” and other documents of Delwinds filed, or to be filed, with the SEC; and

•        other risks and uncertainties described in this joint proxy statement/consent solicitation statement/prospectus, including those under the section entitled “Risk Factors.”

If any of these risks materialize or any of Delwinds’ or FOXO’s assumptions prove incorrect, actual results could differ materially from the results implied by these forward-looking statements. There may be additional risks that neither Delwinds nor FOXO presently know or that Delwinds and FOXO currently believe are immaterial that could also cause actual results to differ materially from those contained in the forward-looking statements. In addition, forward-looking statements reflect Delwinds’ and FOXO’s expectations, plans or forecasts of future events and views as of the date of this joint proxy statement/consent solicitation statement/prospectus. Delwinds and FOXO anticipate that subsequent events and developments may cause Delwinds’ and FOXO’s assessments to change. However, while we may elect to update these forward-looking statements at some point in the future, Delwinds and FOXO specifically disclaim any obligation to do so. These forward-looking statements should not be relied upon as representing Delwinds’ and FOXO’s assessments as of any date subsequent to the date of this joint proxy statement/consent solicitation statement/prospectus. Accordingly, undue reliance should not be placed upon the forward-looking statements. Actual results, performance or achievements may, and are likely to, differ materially, and potentially adversely, from any projections and forward-looking statements and the assumptions on which those forward-looking statements were based. There can be no assurance that the data contained herein is reflective of future performance to any degree. You are cautioned not to place undue reliance on forward-looking statements as a predictor of future performance as projected financial information and other information are based on estimates and assumptions that are inherently subject to various significant risks, uncertainties and other factors, many of which are beyond Delwinds’ and FOXO’s control. Forward-looking statements are not guarantees of performance. All forward-looking statements attributable to Delwinds or FOXO or a person acting on their behalf are expressly qualified in their entirety by the foregoing cautionary statements.

QUESTIONS AND ANSWERS ABOUT THE DELWINDS SPECIAL MEETING

The following questions and answers below only highlight selected information from this document and only briefly address some commonly asked questions about the proposals to be presented at the Delwinds Special Meeting, including with respect to the proposed Business Combination. The following questions and answers do not include all the information that is important to Delwinds stockholders. We urge you to read this entire joint proxy statement/consent solicitation statement/prospectus, including the Annexes and other documents referred to herein, carefully and in their entirety to fully understand the proposed Business Combination and the voting procedures for the Delwinds Special Meeting. See also the section of this joint proxy statement/consent solicitation statement/prospectus titled “Where You Can Find More Information.”

Q:     Why am I receiving this joint proxy statement/consent solicitation statement/prospectus?

A:     Delwinds stockholders are being asked to consider and vote upon a proposal to approve the Business Combination contemplated by the Merger Agreement, among other proposals. Upon the completion of the transactions contemplated by the Merger Agreement, FOXO will become a wholly-owned subsidiary of Delwinds. A copy of the Merger Agreement is attached to this joint proxy statement/consent solicitation statement/prospectus as Annex A.

This joint proxy statement/consent solicitation statement/prospectus and its annexes contain important information about the proposed Business Combination and the other matters to be acted upon at the Delwinds Special Meeting. You should read this joint proxy statement/consent solicitation statement/prospectus and its annexes and the other documents referred to herein carefully and in their entirety.

THE VOTE OF DELWINDS STOCKHOLDERS IS IMPORTANT.    DELWINDS STOCKHOLDERS ARE URGED TO SUBMIT THEIR PROXIES AS SOON AS POSSIBLE AFTER CAREFULLY REVIEWING THIS JOINT PROXY STATEMENT/CONSENT SOLICITATION STATEMENT/PROSPECTUS AND ITS ANNEXES AND CAREFULLY CONSIDERING EACH OF THE PROPOSALS BEING PRESENTED AT THE DELWINDS SPECIAL MEETING.

Q:     What proposals are stockholders of Delwinds being asked to vote upon?

A:     Stockholders of Delwinds are being asked to vote upon the following proposals:

(1)    The NTA Proposal (Proposal 1) — To approve and adopt, subject to the approval of the Business Combination Proposal, the following amendments to the Current Charter (together, the “NTA Amendments”), which shall be effective, if adopted and implemented by Delwinds, prior to the consummation of the proposed Business Combination, to remove from the Current Charter requirements limiting Delwinds’ ability to redeem shares of Delwinds Class A common stock and consummate an initial business combination if the amount of such redemptions would cause Delwinds to have less than $5,000,001 in net tangible assets:

(a)     Section 9.2(a) of the Current Charter shall be deleted in its entirety and replaced with the following language: “Prior to the consummation of the initial Business Combination, the Corporation shall provide all holders of Offering Shares with the opportunity to have their Offering Shares redeemed upon the consummation of the initial Business Combination pursuant to, and subject to the limitations of, Sections 9.2(b) and 9.2(c) (such rights of such holders to have their Offering Shares redeemed pursuant to such Sections, the “Redemption Rights”) hereof for cash equal to the applicable redemption price per share determined in accordance with Section 9.2(b) hereof (the “Redemption Price”). Notwithstanding anything to the contrary contained in this Amended and Restated Certificate, there shall be no Redemption Rights or liquidating distributions with respect to any warrant issued pursuant to the Offering.”

(b)    Section 9.2(e) of the Current Charter shall be deleted in its entirety and replaced with the following language: “If the Corporation offers to redeem the Offering Shares in conjunction with a stockholder vote on an initial Business Combination, the Corporation shall consummate the proposed initial Business Combination only if (i) such initial Business Combination is approved by the affirmative vote of the holders of a majority of the shares of the Common Stock that are voted at a stockholder meeting held to consider such initial Business Combination.”

(c)     The following language shall be removed from Section 9.7 of the Current Charter: “provided, however, that any such amendment will be voided, and this Article IX will remain unchanged, if any stockholders who wish to redeem are unable to redeem due to the Redemption Limitation.”

(2)    The Business Combination Proposal (Proposal 2) — To approve and adopt the Merger Agreement and the transactions contemplated therein pursuant to which at the Effective Time of the Merger:

(a)     each outstanding share of FOXO Class A common stock and FOXO Class B common stock will be cancelled in exchange for the right to receive Class A Common Stock; and

(b)    Delwinds will assume (i) each outstanding option to purchase shares of FOXO common stock, whether vested or unvested (each, an “Assumed Option”), and (ii) each outstanding warrant exercisable for shares of FOXO common stock (whether vested or unvested) (each, an “Assumed Warrant”), in each case that are outstanding immediately prior to the Effective Time, and the Assumed Options and Assumed Warrants will be converted to the right to purchase shares of Class A Common Stock, subject to adjustments in accordance with the terms of the Merger Agreement.

Other than Assumed Options and Assumed Warrants, all other convertible securities and other rights to purchase capital stock of FOXO will be retired and terminated, if they have not been converted, exchanged or exercised for FOXO Class A common stock or FOXO Class B common stock immediately prior to the Effective Time.

We refer to this proposal as the “Business Combination Proposal.” A copy of the Merger Agreement is attached to the joint proxy statement/consent solicitation statement/prospectus as Annex A.

In addition to the approval of the Proposals at the Delwinds Special Meeting, unless waived by the parties to the Merger Agreement, in accordance with applicable law, the closing of the Business Combination is subject to a number of conditions set forth in the Merger Agreement including, among other things, receipt of the requisite stockholder approval contemplated by this joint proxy statement/consent solicitation statement/prospectus. For more information about the closing conditions to the Business Combination, see the section of this joint proxy statement/consent solicitation statement/prospectus titled “Business Combination Proposal — Conditions to the Closing.”

The Merger Agreement may be terminated at any time prior to the Closing of the Business Combination upon agreement of FOXO and Delwinds, or by FOXO or Delwinds acting alone, in specified circumstances. For more information about the termination rights under the Merger Agreement, see the section titled “Business Combination Proposal — Termination.”

Pursuant to the Current Charter, in connection with the Business Combination, Delwinds public stockholders may elect to redeem, effective upon the closing of the Business Combination, shares of Delwinds Class A common stock then held by them for cash equal to the aggregate amount then on deposit in the Trust Account as of two business days prior to the consummation of Delwinds’ Business Combination, including interest earned on the funds held in the Trust Account and not previously released to Delwinds to pay its taxes, divided by the number of then outstanding public shares, subject to the limitations described herein. As of August 19, 2022, based on funds in the Trust Account of approximately $111.9 million as of such date, the pro rata portion of the funds available in the Trust Account for the redemption of public shares of Delwinds Class A common stock was approximately $10.12 per share. Delwinds public stockholders are not required to affirmatively vote for or against the Business Combination in order to redeem their shares of Delwinds Class A common stock for cash. This means that public stockholders who hold shares of Delwinds Class A common stock on or before [          ], 2022 (two (2) business days before the Delwinds Special Meeting) will be eligible to elect to have their shares of Delwinds Class A common stock redeemed for cash in connection with the Delwinds Special Meeting, whether or not they are holders as of the Record Date, and whether or not such shares are voted at the Delwinds Special Meeting.

A public stockholder, together with any of such stockholder’s affiliates or any other person with whom it is acting in concert or as a “group” (as defined under Section 13 of the Exchange Act), will be restricted from redeeming in the aggregate such stockholder’s shares or, if part of such a group, the group’s shares, with respect to 15% or more of the shares of Delwinds common stock included in the units of Delwinds sold in the IPO (including overallotment securities sold to Delwinds’ underwriters in connection with the IPO). Holders of Delwinds’ outstanding public warrants and units do not have redemption rights with respect to

such securities in connection with the Business Combination. Holders of outstanding Delwinds units must separate the underlying shares of Delwinds Class A common stock and public warrants prior to exercising redemption rights with respect to the public Delwinds Class A common stock.

See the section titled “Delwinds Special Meeting — Redemption Rights.”

The Business Combination will be consummated only if the Required Proposals are approved at the Delwinds Special Meeting, which Required Proposals include the Business Combination Proposal, the Charter Proposal, the Incentive Plan Proposal, the Management Contingent Share Plan Proposal, the Director Election Proposal, and the NYSE Proposal. The Required Proposals are conditioned on the approval of the Business Combination Proposal. The Advisory Charter Proposals and the Insider Letter Amendment Proposal are conditioned on the Required Proposals. The NTA Proposal is conditioned upon the approval of the Business Combination Proposal. Therefore, if the Business Combination Proposal is not approved, then the NTA Proposal will have no effect, even if approved by Delwinds stockholders. The Adjournment Proposal is not conditioned on the approval of any other proposal set forth in this joint proxy statement/consent solicitation statement/prospectus.

The Business Combination involves numerous risks. For more information about these risks, see the section titled “Risk Factors.”

(3)     The Charter Proposal (Proposal 3) — Assuming the Business Combination Proposal (Proposal 2) is approved and adopted, to approve and adopt the Proposed Charter, in the form attached to this joint proxy statement/consent solicitation statement/prospectus as Annex B (the “Proposed Charter”), which will amend and restate the Current Charter (as amended by the NTA Proposal, if approved) in its entirety and be effective when duly filed with the Secretary of State of the State of Delaware in connection with the Closing.

(4)    Advisory Charter Proposals (Proposals 4 – 7) — To consider and vote upon, on a non-binding basis, certain governance provisions in the Proposed Charter, presented separately in accordance with SEC requirements. A summary of these provisions is set forth in the “Advisory Charter Proposals (Proposals 4 – 7)” section of this joint proxy statement/consent solicitation statement/prospectus and a complete copy of these provisions is attached to the joint proxy statement/consent solicitation statement/prospectus as Annex B. You are encouraged to read them in their entirety.

(5)    The Incentive Plan Proposal (Proposal 8) — To approve and adopt an equity incentive award plan established to be effective as of the Closing of the Business Combination. A summary of the Incentive Plan is set forth in the “The Incentive Plan Proposal (Proposal 8)” section of this joint proxy statement/consent solicitation statement/prospectus and a complete copy of the Incentive Plan is attached to the joint proxy statement/consent solicitation statement/prospectus as Annex D. You are encouraged to read the Incentive Plan in its entirety.

(6)    Management Contingent Share Plan Proposal (Proposal 9) — To approve and adopt an earnout incentive plan (referred to as the Management Contingent Share Plan) to be effective following the Closing. A summary of the Management Contingent Share Plan is set forth in the “Management Contingent Share Plan Proposal (Proposal 9)” section of this joint proxy statement/consent solicitation statement/prospectus and a complete copy of the Management Contingent Share Plan is attached to the joint proxy statement/consent solicitation statement/prospectus as Annex E. You are encouraged to read the Management Contingent Share Plan in its entirety.

(7)    Insider Letter Amendment Proposal (Proposal 10) — To approve and adopt a proposal to amend, effective at the Closing, the lock-up period applicable to certain shares of Delwinds stock held by the Sponsor set forth in the Insider Letter, dated December 20, 2020, by and among Delwinds, the Sponsor and directors and officers of Delwinds, to reduce this period from one year to six months after the consummation of the Business Combination. A summary of this letter is set forth in the “Insider Letter Amendment Proposal (Proposal 10)” section of this joint proxy statement/consent solicitation statement/prospectus and a complete copy of this amendment is attached to the joint proxy statement/consent solicitation statement/prospectus as Annex F. You are encouraged to read this amendment in its entirety.

(8)    The NYSE Proposal (Proposal 11) — To consider and vote upon, for purposes of complying with the applicable listing rules of the NYSE, the issuance of more than 20% of Delwinds common stock in connection with the Business Combination, the Support Subscription Agreements and the Cantor Agreement.

(9)    The Director Election Proposal (Proposal 12) — To consider and vote upon the election of four (4) directors, who, upon consummation of the Business Combination, will constitute all the members of the board of directors of the Combined Company.

(10)  The Adjournment Proposal (Proposal 13) — To consider and vote upon a proposal to adjourn the Delwinds Special Meeting to a later date or dates, if necessary or appropriate as determined by the Delwinds Board.

Q:     What interests do Delwinds’ initial stockholders and current officers and directors and its financial advisors have in the Business Combination?

A:     In considering the recommendation of Delwinds’ Board to vote in favor of the Business Combination, Public Stockholders should be aware that, aside from their interests as stockholders, Delwinds’ initial stockholders, directors and officers have interests in the Business Combination that are different from, or in addition to, those of Delwinds’ other stockholders generally, including the aggregate amount at risk to the Delwinds’ initial stockholders of $6,350,000, which is the amount paid for the Founder Shares and the Private Units. Delwinds’ directors and the members of the Special Committee were aware of and considered these interests, among other matters, in evaluating the Business Combination, and in recommending to Delwinds stockholders that they approve the Business Combination. Further, the interests of members of the Sponsor or current officers or directors of Delwinds may be different from or in addition to (and which may conflict with) your interests and may be incentivized to complete a less favorable business combination rather than liquidating Delwinds. Public Stockholders should take these interests into account in deciding whether to approve the Business Combination. These interests include, among other things:

•        the fact that, unless Delwinds consummates an initial business combination, Delwinds’ officers, directors and the Sponsor will not receive reimbursement for any out-of-pocket expenses incurred by them to the extent that such expenses exceed the amount of available proceeds not deposited in the Trust Account (as of August 19, 2022, none of Delwinds’ officers and directors have incurred any out-of-pocket expenses);

•        the fact that, as a condition to the IPO, pursuant to the Insider Letter, the initial stockholders’ Founder Shares became subject to a lock-up whereby, subject to certain limited exceptions, the Founder Shares are not transferable or salable until the earlier of (A) one year after the completion of our initial business combination or (B) subsequent to our initial business combination, (x) if the last reported sale price of the Delwinds Class A common stock equals or exceeds $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period commencing at least 150 days after our initial business combination, or (y) the date on which Delwinds completes a liquidation, merger, capital stock exchange, reorganization or other similar transaction that results in all of Delwinds stockholders having the right to exchange their shares of common stock for cash, securities or other property (while the Founder Shares are not the same as the Delwinds Class A common stock, are subject to certain restrictions that are not applicable to the Delwinds Class A common stock, and may become worthless if Delwinds does not complete a business combination by September 15, 2022 (or such other date as approved by the Delwinds stockholders), the aggregate value of the 5,031,250 Founder Shares owned by Delwinds’ initial stockholders is estimated to be approximately $50.7 million, assuming the per share value of the Founder Shares is the same as the $10.08 closing price of the Delwinds Class A common stock on the NYSE on August 19, 2022);

•        the fact that the initial stockholders purchased an aggregate of 632,500 Private Units, each consisting of one share of Delwinds Class A common stock, and one-half of one redeemable warrant, with each whole warrant entitling the holder thereof to purchase one share of Delwinds Class A common stock for $11.50 per share, for a purchase price of $6,325,000, or $10.00 per Private Unit, in the Private Placement consummated simultaneously with the IPO, which warrants will be worthless if a business combination is

not consummated (although the Private Warrants have certain rights that differ from the rights of holders of the Public Warrants, the aggregate value of the 632,500 Private Units held by the Sponsor is estimated to be approximately $6.5 million, assuming the per unit value of the Private Units is the same as the $10.16 closing price of the Public Units on the NYSE on August 19, 2022);

•        the fact that the initial stockholders have agreed that the Private Warrants, and all of their underlying securities, will not be sold or transferred by it until 30 days after Delwinds has completed a business combination, subject to limited exceptions;

•        the fact that the Sponsor purchased from Delwinds 5,750,000 shares of the Delwinds Class B common stock for an aggregate price of $25,000 (on November 30, 2020, the Sponsor returned to Delwinds, at no cost, an aggregate of 718,750 Founder Shares, which Delwinds cancelled, resulting in an aggregate of 5,031,250 Founder Shares outstanding and held by the Sponsor) and paid $6,325,000 to purchase 632,500 Private Units for an aggregate purchase price of $6,350,000, which will have a significantly higher value at the time of the Business Combination, if it is consummated, and, based on the closing trading price of the Class A common stock on August 19, 2022, which was $10.08, would have an aggregate value of $50.7 million as of the same date and including the purchase of the Private Units and based on the closing trading price of the Public Units on August 19, 2022, which was $10.16, would have an aggregate value of $6.4 million. If Delwinds does not consummate the Business Combination or another initial business combination by September 15, 2022 (or such other date as approved by the Delwinds stockholders), and Delwinds is therefore required to be liquidated, these shares would be worthless, as Founder Shares are not entitled to participate in any redemption or liquidation of the Trust Account. Based on the difference in the effective purchase price of $0.005 per share that the members of the Sponsor paid for the Founder Shares, as compared to the purchase price of $10.00 per Unit sold in the IPO, members of the Sponsor may earn a positive rate of return even if the share price of the Combined Company after the Closing falls below the price initially paid for the Units in the IPO and the Delwinds public stockholders experience a negative rate of return following the Closing of the Business Combination;

•        the fact that the initial stockholders have agreed not to redeem any of their Founder Shares in connection with a stockholder vote to approve a proposed initial business combination;

•        the fact that, if Delwinds does not complete an initial business combination by September 15, 2022 (or such other date as approved by the Delwinds stockholders), a portion of the proceeds from the sale of the Private Warrants will be included in the liquidating distribution to Delwinds’ public stockholders and the Private Warrants will expire worthless;

•        the fact that, if the Trust Account is liquidated, including in the event Delwinds is unable to complete an initial business combination within the required time period, the Sponsor has agreed that it will be liable to Delwinds, if and to the extent any claims by a third party for services rendered or products sold to Delwinds, or a prospective target business with which Delwinds has entered into a written letter of intent, confidentiality or similar agreement or Merger Agreement, reduce the amount of funds in the Trust Account to below the lesser of (i) $10.00 per public share and (ii) the actual amount per public share held in the Trust Account as of the date of the liquidation of the Trust Account, if less than $10.00 per share due to reductions in the value of the trust assets, less taxes payable from interest, provided that such liability will not apply to any claims by a third party or prospective target business who executed a waiver of any and all rights to the monies held in the Trust Account (whether or not such waiver is enforceable) nor will it apply to any claims under Delwinds’ indemnity of the underwriters of the initial public offering against certain liabilities, including liabilities under the Securities Act;

•        the fact that, pursuant to the Underwriting Agreement entered into by Delwinds and the IPO Underwriters, underwriting commissions of $3,021,875 (the “Deferred UW Fee”), if any, will be payable to Cantor and Cantor will also be reimbursed for reasonable out-of-pocket costs and expenses associated with services performed in connection with the IPO. Accordingly, Cantor has an interest in Delwinds completing the Business Combination because if the Business Combination, or another initial business combination, is not consummated, the Deferred UW Fee will not be received by Cantor and these expenses will not be reimbursed;

•        On February 23, 2022, Delwinds issued a promissory note in the principal amount of up to $2,000,000 to the Sponsor (the “Sponsor February Promissory Note”) for working capital expenses. As of August 19, 2022, Delwinds had drawn down $560,000 under the Sponsor February Promissory Note;

•        the fact that, if the Business Combination or another initial business combination is not consummated, the Sponsor February Promissory Note, which note may be repaid in cash or, at the election of the Sponsor, in the form of units of Delwinds (the “Conversion Units”) with terms equivalent to the terms of outstanding Private Units, at the closing of the Business Combination, may not be repaid to Sponsor, in whole or in part and persons or entities that provided the funds made available to Delwinds for working capital purposes in connection with the Sponsor February Promissory Note will not be repaid the amounts that they contributed for this purpose;

•        the fact that, if the Business Combination is not consummated, the Subscription Investors, which are comprised of Andrew J. Poole, Delwinds’ Chairman and Chief Executive Officer, and The Gray Insurance Company, which is affiliated with the Sponsor and of which Delwinds director Michael Gray, is principal executive and President, will not be obligated and will not purchase shares of Class A Common Stock pursuant to the terms and conditions of the Support Subscription Agreements, in spite of time and expense that they may have devoted to negotiating and entering into such arrangements;

•        the fact that, if the Business Combination is not consummated, and The Gray Insurance Company, which is affiliated with the Sponsor and of certain directors and officers of Delwinds, will remain invested in FOXO and such investment may be illiquid or may not provide a positive rate of return to and The Gray Insurance Company; and

•        the fact that Andrew J. Poole is an anticipated nominee to the Combined Company Board and, as such, after the proposed Business Combination is consummated, Mr. Poole will in the future receive any cash fees, stock options or stock awards that the Combined Company Board determines to pay to its directors.

These interests may have influenced Delwinds’ directors in making their recommendation that you vote in favor of the approval of the Business Combination.

Q:     Why is the NTA Proposal being proposed?

A:     The adoption of the proposed amendments to remove the net asset test limitation from the Current Charter is being proposed in order to facilitate the consummation of the Business Combination, by permitting redemptions by public stockholders even if such redemptions result in Delwinds having net tangible assets that are less than $5,000,001. The purpose of the net asset test limitation was initially to ensure that the Delwinds Class A common stock is not deemed to be a “penny stock” pursuant to Rule 3a51-1 under the Exchange Act. Because the Delwinds Class A common stock and the Combined Company’s common stock would not be deemed to be a “penny stock,” as such securities are listed on a national securities exchange, Delwinds is presenting the NTA Proposal to facilitate the consummation of the Business Combination. At the Closing, if Delwinds has less than $5,978,125 in cash or cash equivalents, the Subscription Investors will purchase Class A common stock in accordance with the obligations set forth in the Support Subscription Agreements (as adjusted as a result of the RBCCM Resignation), prior to the Business Combination, which may facilitate the consummation of the Business Combination. For more information, see “The NTA Proposal (Proposal No. 1) — Reasons for the Amendments.”

Q:     Are the proposals conditioned on one another?

A:     Yes. Each of the Business Combination Proposal, the Charter Proposal, the Incentive Plan Proposal, the Management Contingent Share Plan Proposal, the Director Election Proposal, and the NYSE Proposal, are referred to herein as “Required Proposals.” The remaining Proposals, consisting of the NTA Proposal, the Advisory Charter Proposals, the Insider Letter Amendment Proposal, and the Adjournment Proposal, are not Required Proposals. Unless the Business Combination Proposal is approved, the Required Proposals will not be presented to the stockholders of Delwinds at the Delwinds Special Meeting, because they are conditioned on the approval of the Business

Combination Proposal. The Business Combination Proposal, the Advisory Charter Proposals and the Insider Letter Amendment Proposal are likewise conditioned on the approval of these Required Proposals. The NTA Proposal is conditioned upon the approval of the Business Combination Proposal. Therefore, if the Business Combination Proposal is not approved, then the NTA Proposal will have no effect, even if approved by Delwinds stockholders. The approval of the Business Combination Proposal and the other Required Proposals are preconditions to the consummation of the Business Combination. The Adjournment Proposal is not conditioned on the approval of any other proposal set forth in this joint proxy statement/consent solicitation statement/prospectus.

It is important for you to note that if the Business Combination Proposal does not receive the requisite vote for approval, Delwinds will not consummate the Business Combination. If Delwinds does not consummate the Business Combination and fails to complete an initial business combination by September 15, 2022 (or such other date as approved by the Delwinds stockholders), Delwinds will be required, in accordance with the Current Charter, to dissolve and liquidate its Trust Account by returning the then-remaining funds in such account (less amounts released to pay franchise and income tax obligations and up to $100,000 for dissolution expenses, and amounts paid pursuant to redemptions) to its public stockholders. On June 6, 2022, at a special meeting of Delwinds’ stockholders (the “Extension Meeting”), Delwinds’ stockholders approved the Extension Amendment, which extends the date by which Delwinds must consummate its initial business combination from June 15, 2022 to September 15, 2022 (or such earlier date as determined by the Delwinds Board). If Delwinds’ initial business combination is not consummated by September 15, 2022, then Delwinds’ existence will terminate, and Delwinds will distribute amounts in the Trust Account as provided in Delwinds’ Current Charter.

Q:     When and where will the Delwinds Special Meeting take place?

A:     The Delwinds Special Meeting will be held on [          ], 2022 at [          ], Eastern Time, via live audio webcast or such other date, time and place to which such meeting may be adjourned or postponed, to consider and vote upon the proposals.

Q:     What will happen in the Business Combination?

A:      At the Closing, Merger Sub will merge with and into FOXO, with FOXO surviving such Merger, as a result of which FOXO Stockholders (except those who properly exercise appraisal or dissenters rights under applicable law) will receive newly issued shares of Class A Common Stock, and the Assumed Options and Assumed Warrants will be assumed by Delwinds. For details and more information please see the sections entitled “Business Combination Proposal (Proposal 2) — the Merger Agreement — Consideration to FOXO Stockholders in the Merger.” Upon consummation of the Business Combination, FOXO will become a wholly-owned subsidiary of Delwinds. After the Closing of the Business Combination, the cash held in the Trust Account will be released from the Trust Account and used to pay each of Delwinds’ and FOXO’s transaction expenses and other liabilities of Delwinds due as of the Closing, and for working capital and general corporate purposes. A copy of the Merger Agreement is attached to this joint proxy statement/consent solicitation statement/prospectus as Annex A.

Q:     What equity stake will current Delwinds stockholders and FOXO Stockholders hold in the Combined Company immediately after the Closing?

A:     Upon consummation of the Business Combination (assuming, among other things, that no additional Public Stockholders exercise redemption rights in connection with the Closing and the other assumptions described under the section with the heading “Frequently Used Terms — Share Calculations and Ownership Percentages”), (i) Delwinds’ public stockholders are expected to own approximately 26.5% of the outstanding Combined Company common stock, (ii) the Sponsor and initial stockholders are expected to own approximately 13.6% of the outstanding Combined Company common stock, (iii) the FOXO Stockholders (without taking into account any public shares held by FOXO Stockholders prior to the consummation of the Business Combination) are expected to own approximately 59.5% of the Combined Company common stock, (iv) no Class A Common Stock is purchased pursuant to the Support Subscription Agreements, and (v) at the Closing 160,000 shares of Class A Common Stock in satisfaction of the Cantor Commitment Fee.

These percentages assume, among other assumptions, that at, or in connection with, the Closing, (i) 9,200,000 Management Contingent Shares are issued to members of Combined Company management, (ii) no additional public stockholders exercise their redemption rights in connection with the Business Combination, (iii) 15,653,859 shares of Class A Common Stock are issued to former stockholders of FOXO in accordance with the Merger Agreement,

and (iv) no awards are issued under the Incentive Plan. If actual facts are different from these assumptions, the percentage ownership retained by the Delwinds stockholders and FOXO stockholders in the Combined Company, and associated voting power, will be different.

If any of Delwinds’ public stockholders exercise redemption rights in connection with the Closing, the percentage of the Combined Company’s outstanding common stock held by Delwinds’ public stockholders will decrease and the percentages of the Combined Company’s outstanding common stock held by the Sponsor and by the FOXO Stockholders will increase, in each case, relative to the percentage held if none of the shares of Delwinds Class A common stock are redeemed.

If any of Delwinds’ public stockholders as of August 19, 2022 redeem their Public Shares at Closing in accordance with the Current Charter but continue to hold Public Warrants after the Closing, the aggregate value of the Public Warrants that may be retained by them, based on the closing trading price per Public Warrant of $0.22 as of August 19, 2022, would be approximately $2.2 million, regardless of the number of shares redeemed by Public Stockholders. Upon the issuance of the Combined Company common stock in connection with the Business Combination, the percentage ownership of the Combined Company by Delwinds’ public stockholders who do not redeem their Public Shares will be diluted. Delwinds public stockholders that do not redeem their Public Shares in connection with the Business Combination will experience further dilution upon the exercise of Public Warrants that are retained after the Closing by redeeming Delwinds public stockholders. The percentage of the total number of outstanding shares of Common Stock that will be owned by Delwinds public stockholders as a group will vary based on the number of Public Shares for which the holders thereof elect to have redeemed in connection with the Business Combination.

The following table illustrates varying ownership levels of the Combined Company immediately following the Business Combination:

____________

(1)      Includes 160,000 shares of Class A Common Stock representing the Cantor Commitment Fee.

(2)      Assumes that 11,047,578 Public Shares are redeemed for aggregate redemption payments of approximately $111.6 million, assuming a $10.105 per share Redemption Price, based on three months of payments made to the Trust Account as a result of the Extension Loan.

For additional information regarding assumptions incorporated into the information presented above, including, without limitation, “maximum redemptions,” see the sections titled “Frequently Used Terms — Share Calculations and Ownership Percentages,” “Unaudited Pro Forma Condensed Combined Financial Information” and “Business Combination Proposal — The Merger Agreement — Consideration to FOXO Stockholders in the Merger.”

Q:     What conditions must be satisfied to complete the Business Combination?

A:     In addition to the Required Proposals, there are a number of closing conditions in the Merger Agreement, including the approval by the stockholders of FOXO of the Business Combination. For a summary of the conditions that must be satisfied or waived prior to the Closing of the Business Combination, see the section titled “The Business Combination Proposal (Proposal 2) — The Merger Agreement” and “Summary of the Joint Proxy Statement/Consent Solicitation/Prospectus The Proposals — The Business Combination Proposal (Proposal 2) — Conditions to Closing.”

Q:     Why is Delwinds providing stockholders with the opportunity to vote on the Business Combination?

A:     Under the Current Charter, Delwinds must provide all holders of its Public Shares with the opportunity to have their Public Shares redeemed upon the consummation of Delwinds’ initial business combination either in conjunction with a tender offer or in conjunction with a stockholder vote. For business and other reasons, Delwinds has elected to provide its stockholders with the opportunity to have their Public Shares redeemed

in connection with a stockholder vote rather than a tender offer. Therefore, Delwinds is seeking to obtain the approval of its stockholders of the Business Combination Proposal in order to allow its public stockholders to effectuate redemptions of their Public Shares in connection with the Closing of the Business Combination.

Q:     What are the potential impacts on the Business Combination and related transactions resulting from the resignation of RBCCM and DB?

A:     On June 1, 2022, RBCCM resigned from its role as capital markets advisor and financial advisor to Delwinds in connection with the Business Combination and waived all rights to any fees and compensation in connection with such roles, as well as any deferred fees due under the Underwriting Agreement and Delwinds mutually accepted this resignation. All such fees and compensation were only payable to RBCCM upon completion of the Business Combination. In addition, RBCCM delivered notice of resignation to the Securities and Exchange Commission pursuant to Section 11(b)(1) under the Securities Act. See “Summary — Recent Developments.”

On June 16, 2022, DB resigned from its role as financial advisor to FOXO in connection with the Business Combination and waived all rights to any fees and compensation in connection with such roles, and FOXO mutually accepted this resignation. All such fees and compensation were only payable to DB upon completion of the Business Combination. In addition, DB delivered notice of resignation to the Securities and Exchange Commission pursuant to Section 11(b)(1) under the Securities Act. See “Summary — Recent Developments.”

As a result of the RBCCM Resignation and the DB Resignation, and the associated waivers of fees, the transactions fees payable by Delwinds and FOXO at the consummation of the Business Combination will be reduced by approximately $12.6 million. The IPO underwriting services being provided by RBCCM and the financial advisory services being provided by RBCCM and DB prior to such resignations were substantially complete at the time of its resignation, with any fees payable to RBCCM and DB for such services contingent upon the Closing of the Business Combination.

We believe that the resignation of RBCCM and DB, and the waiver of fees for services that have already been substantially rendered or that were contingent upon the occurrence of an event that applicable persons expect will occur, is unusual. While RBCCM and DB did not provide any additional detail in their termination letters, stockholders should be aware that such resignations indicate that neither RBCCM nor DB wants to be associated with the disclosures in this proxy statement/prospectus or the underlying business analysis related to the transaction described herein. Delwinds public stockholders may be more likely to elect to redeem their shares as a result of such resignations and waivers and the proceeds that the Combined Company receives as a result of the Business Combination may be reduced as a result of such resignations and waivers.

Q:     If the NTA Proposal is not approved by the Delwinds stockholders and the net tangible assets requirement in the Current Charter remains applicable, are there any arrangements to help ensure that Delwinds will have sufficient funds, together with the proceeds in its Trust Account, to meet the net tangible assets requirement in the Current Charter for consummating the Business Combination?

A:     Yes. In connection with the execution of the Merger Agreement, Delwinds entered into Support Subscription Agreements with certain investors pursuant to which, in the event that cash and cash equivalents in the Trust Account as of the Closing, after satisfaction of Redemptions but prior to payment of expenses and liabilities due at the Closing, are less than the Threshold Amount (which is subject to reduction in accordance with the terms of the Support Subscription Agreements, such investors initially agreed to purchase up to an aggregate of 1,000,000 shares of Class A Common Stock for an aggregate purchase price of $10,000,000 or $10.00 per share), which, as a result of the RBCCM Resignation was reduced to $5,978,125, resulting in such investors being required to purchase up to an aggregate of 597,813 shares of Class A Common Stock for an aggregate purchase price of $5,978,125 or $10.00 per share.

The proceeds from the Trust Account will be used to pay any loans owed by Delwinds if the initial Business Combination is completed, stockholders who properly exercise their redemption rights, for any Delwinds transaction expenses or other administrative expenses incurred by Delwinds, and to pay all unpaid transaction expenses of FOXO and any remainder will be used for general corporate purposes, including, but not limited to, working capital for operations, capital expenditures and future acquisitions. In addition, Delwinds and/or FOXO may seek to arrange for additional third-party financing which may be in the form of debt (including bank debt or convertible notes) or equity, the proceeds of which would be used for a variety of purposes including, in the case of Delwinds, to meet the net tangible assets condition for consummating the Business Combination.

Q:     How many votes do I have at the Delwinds Special Meeting?

A:     Delwinds stockholders are entitled to one vote at the Delwinds Special Meeting for each share of Delwinds common stock held of record as of August 19, 2022, the record date for the Delwinds Special Meeting (the “Record Date”). Holders of Delwinds Class A common stock and Delwinds Class B common stock will vote together as one class on all Proposals. As of the close of business on the Record Date, there were 5,031,250 outstanding shares of Delwinds Class B common stock and 11,680,078 outstanding shares of Delwinds Class A common stock.

Q:     What vote is required to approve the proposals presented at the Delwinds Special Meeting?

A:     The approval of the NTA Proposal requires the affirmative vote of holders of sixty-five percent (65%) of the issued and outstanding shares of Delwinds common stock as of the Record Date, and the approval of the Charter Proposal requires the affirmative vote of holders of a majority of the issued and outstanding shares of Delwinds common stock as of the Record Date. Accordingly, a Delwinds stockholder’s failure to vote by proxy or to vote in person at the Delwinds Special Meeting, or an abstention (if a valid quorum is established for the meeting), will have the same effect as a vote “AGAINST” the NTA Proposal and the Charter Proposal. Approval of the Charter Proposal is a condition to the approval of the Business Combination. The approval of the Director Election Proposal requires the affirmative vote of holders of at least a plurality of the shares of Delwinds common stock cast by the stockholders represented in person online or by proxy and entitled to vote thereon at the Delwinds Special Meeting.

In contrast, the approval of the remaining Proposals (including the Business Combination Proposal) each require the affirmative vote of the holders of a majority of the shares of Delwinds common stock cast by the stockholders, which are represented in person or by proxy and entitled to vote thereon at the Delwinds Special Meeting. As a result, a Delwinds stockholder’s failure to vote by proxy or to vote in person in respect of those remaining Proposals (including the Business Combination Proposal) at the Delwinds Special Meeting, or to abstain, will not be counted for or against the number of shares of Delwinds common stock required for the vote on those Proposals.

If the Business Combination Proposal is not approved, the Required Proposals will not be presented to the Delwinds stockholders for a vote, although the Adjournment Proposal may be presented. The NTA Proposal is conditioned upon the approval of the Business Combination Proposal. Therefore, if the Business Combination Proposal is not approved, then the NTA Proposal will have no effect, even if approved by Delwinds stockholders. The approval of the Business Combination Proposal and the other Required Proposals are preconditions to the consummation of the Business Combination.

The Sponsor and Delwinds’ directors and officers have agreed to vote their shares in favor of the Business Combination and the Merger, including the Business Combination Proposal and the other Proposals.

Q:     What constitutes a quorum at the Delwinds Special Meeting?

A:     Holders present in person or by proxy of shares of issued and outstanding Delwinds common stock representing a majority of the voting power of all outstanding shares of Delwinds common stock entitled to vote at the Delwinds Special Meeting constitute a quorum. In the absence of a quorum, the chairman of the meeting has the power to adjourn the Delwinds Special Meeting. As of the Record Date, 8,355,665 shares of Delwinds common stock would be required to achieve a quorum.

Q:     May the Sponsor or Delwinds’ directors, officers, advisors or their affiliates purchase shares in connection with the Business Combination?

A:     In connection with the stockholder vote to approve the proposed Business Combination, the Sponsor, or Delwinds’ directors, officers or advisors or their respective affiliates may privately negotiate transactions to purchase shares from stockholders who would have otherwise elected to have their shares redeemed in conjunction with a proxy solicitation pursuant to the proxy rules for a per-share pro rata portion of the Trust Account. None of Delwinds’ Sponsor or the other members of the Sponsor, directors, officers or advisors or their respective affiliates will make any such purchases when they are in possession of any material non-public information not disclosed to the seller or during a restricted period under Regulation M under the Securities Exchange Act of 1934, as amended (the “Exchange Act”). Such a purchase would include a contractual acknowledgement that such stockholder, although still the record holder of Delwinds’ shares, is no longer the beneficial owner thereof and therefore agrees not to exercise its redemption rights, and could include a contractual provision that directs such stockholder to vote such shares in a manner directed by the purchaser. In the event that the Sponsor or any other member of the Sponsor or Delwinds’ directors, officers or advisors or their respective affiliates purchase shares in privately negotiated transactions from public stockholders who have already elected to exercise their redemption rights, such selling stockholders would be required to revoke their prior elections to redeem their shares. Any such privately negotiated purchases may be transacted at purchase prices that are below or in excess of the per-share pro rata portion of the Trust Account.

Q:     How will the Sponsor and the directors and officers of Delwinds vote?

A:     The Sponsor and Delwinds’ officers and directors each entered into the Insider Letter, pursuant to which they have agreed to vote their Founder Shares and any public shares purchased during or after Delwinds’ initial public offering (including in open market and privately negotiated transactions) in favor of the Business Combination, including each of the Proposals. Accordingly, because of the Insider Letter, it is more likely that the necessary stockholder approval for the Proposals will be received.

Q:     What interests do FOXO’s current officers and directors have in the Business Combination?

A:      Members of the FOXO Board and FOXO’s executive officers have interests in the Business Combination that may be different from or in addition to (and which may conflict with) your interests. These interests include, among others, upon consummation of the Merger Agreement: (i) certain members of the FOXO Board and FOXO’s executive officers will be awarded restricted stock awards under the Management Contingent Share Plan, (ii) certain members of the FOXO Board are expected to serve as members of the Combined Company Board, (iii) certain of FOXO’s executive officers will enter into employment agreements with the Combined Company in connection with the Business Combination, and (iv) certain members of the FOXO Board and executive officers hold equity interests in FOXO, which will be converted into the right to receive equity interests in the Combined Company in connection with the Business Combination. Additionally, in connection with the Extension Amendment, on June 6, 2022, FOXO agreed to provide Delwinds the Extension Loan in an aggregate principal amount of up to $1,159,995.69 to be deposited into the Trust Account for each Public Share that was not redeemed in connection with the extension of Delwinds’ termination date for each month past June 15, 2022 until September 15, 2022, which was drawn down in three equal amounts of $386,665.23 per withdrawal, between the 15th and 22nd of each of June, July and August 2022. If the Business Combination is not consummated, Delwinds is not obligated to repay the Extension Loan and any funds loaned thereunder will not be recovered by FOXO.

Please see the sections entitled “Risk Factors” and “The Business Combination Proposal (Proposal 2) — Interests of FOXO’s Directors and Officers in the Business Combination” and “Executive and Director Compensation of FOXO — Employment Agreements and Other Arrangements with Executive Officers and Directors” of this joint proxy statement/consent solicitation statement/prospectus for a further discussion of these interests.

Q:     How do the Public Warrants differ from the Private Warrants and what are the related risks to any holders of Public Warrants following the Business Combination?

A:     The Private Warrants are identical to the Public Warrants in all material respects, except that the Private Warrants will not be transferable, assignable or salable until 30 days after the completion of the Business Combination and they will not be redeemable by the Combined Company so long as they are held by the Sponsor or its permitted transferees. The Sponsor, or its permitted transferees, has the option to exercise the Private Warrants on a cashless basis. If the Private Warrants are held by holders other than the Sponsor or its permitted transferees, the Private Warrants will be redeemable by the Combined Company in all redemption scenarios and exercisable by the holders on the same basis as the Public Warrants.

Following the Business Combination, the Combined Company may redeem the Public Warrants, prior to their exercise at a time that is disadvantageous to the holder, thereby significantly impairing the value of such warrants. The Combined Company will have the ability to redeem outstanding Public Warrants at any time after they become exercisable and prior to their expiration, at a price of $0.01 per warrant, provided that the closing price of the Class A Common Stock equals or exceeds $18.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within a 30 trading day period ending on the third trading day prior to the date on which a notice of redemption is sent to the warrantholders. The Combined Company will not redeem the warrants as described above unless a registration statement under the Securities Act covering the Class A Common Stock issuable upon exercise of such warrants is effective and a current prospectus relating to those shares of Class A Common Stock is available throughout the 30-day redemption period, except if the warrants may be exercised on a cashless basis and such cashless exercise is exempt from registration under the Securities Act. If and when the Public Warrants become redeemable by the Combined Company, if the Combined Company has elected to require the exercise of Public Warrants on a cashless basis, the Combined Company will not redeem the warrants as described above if the issuance of shares of Class A Common Stock upon exercise of Public Warrants is not exempt from registration or qualification under applicable state blue sky laws or the Combined Company is unable to effect such registration or qualification. Redemption of the outstanding Public Warrants could force you

(i) to exercise your Public Warrants and pay the exercise price therefor at a time when it may be disadvantageous for you to do so, (ii) to sell your Public Warrants at the then-current market price when you might otherwise wish to hold your Public Warrants, or (iii) to accept the nominal redemption price which, at the time the outstanding Public Warrants are called for redemption, is likely to be substantially less than the market value of your Public Warrants.

In the event the Combined Company determines to redeem the Public Warrants, holders of our redeemable warrants would be notified of such redemption as described in our warrant agreement. Specifically, in the event that the Company elects to redeem all of the redeemable warrants as described above, the Company will fix a date for the redemption (the “Redemption Date”). Notice of redemption will be mailed by first class mail, postage prepaid, by the Combined Company not less than 30 days prior to the Redemption Date to the registered holders of the redeemable warrants to be redeemed at their last addresses as they appear on the registration books. Any notice mailed in the manner provided in the warrant agreement will be conclusively presumed to have been duly given whether or not the registered holder received such notice. In addition, beneficial owners of the redeemable warrants will be notified of such redemption via the Combined Company’s posting of the redemption notice to DTC.

The closing price for the Delwinds Class A Common Stock as of August 19, 2022 was $10.08 and has never exceeded the $18.00 threshold that would trigger the right to redeem the Public Warrants following the Closing.

Q:     What happens if I sell my shares of Delwinds Class A common stock before the Delwinds Special Meeting?

A:     The Record Date is earlier than the date of the Delwinds Special Meeting. If you transfer your shares of Delwinds Class A common stock after the Record Date, but before the Delwinds Special Meeting, unless the transferee obtains a proxy from you to vote those shares, you will retain your right to vote at the Delwinds Special Meeting. However, you will not be able to seek redemption of your shares because you will no longer be able to deliver them for cancellation upon consummation of the Business Combination in accordance with the provisions described herein. If you transfer your shares of Delwinds Class A common stock prior to the Record Date, you will have no right to vote those shares at the Delwinds Special Meeting.

Q:     What happens if a substantial number of the public stockholders vote in favor of the Business Combination and exercise their redemption right?

A:     Delwinds stockholders who vote in favor of the Business Combination may nevertheless also exercise their redemption rights. Accordingly, the Business Combination may be consummated even though the funds available from the Trust Account and the number of public stockholders are reduced as a result of redemptions by public stockholders. Nonetheless, unless the NTA Proposal is approved, the consummation of the Business Combination is conditioned upon, among other things, the net tangible assets condition required in the Current Charter of having $5,000,001 immediately prior to or upon consummation of the Business Combination. In addition, with fewer Public Shares and public stockholders, the trading market for the Combined Company’s stock may be less liquid than the market for Delwinds common stock was prior to consummation of the Business Combination and Combined Company may not be able to meet the listing standards of the NYSE. In addition, with less funds available from the Trust Account, the working capital infusion from the Trust Account into FOXO’s business will be reduced. As a result, the proceeds will be greater in the event that no public stockholders exercise redemption rights with respect to their public shares for a pro rata portion of the Trust Account as opposed to the scenario in which Delwinds’ public stockholders exercise the maximum allowed redemption rights.

Q:     What happens if I vote against any of the Required Proposals (consisting of the Business Combination Proposal, the Charter Proposal, the Incentive Plan Proposal, the Management Contingent Share Plan Proposal and the NYSE Proposal)?

A:     If any of the Required Proposals are not approved, the Business Combination is not consummated and Delwinds does not otherwise consummate an alternative business combination by September 15, 2022 (or such other date as approved by the Delwinds stockholders), pursuant to the Current Charter, Delwinds will be required to dissolve and liquidate its Trust Account by returning the then-remaining funds in such account to the public stockholders, unless Delwinds seeks and obtains the consent of its stockholders to amend the Current Charter to extend the date by which it must consummate its initial business combination (an “Extension”), in which event, Delwinds’ public stockholders will be entitled to redemption rights in accordance with the Current Charter. On June 6, 2022, Delwinds’ stockholders approved the Extension Amendment, which extends the date by which Delwinds must consummate its initial business combination from June 15, 2022 to September 15, 2022 (or such earlier date as determined by the Delwinds Board). If Delwinds’ initial business combination is not consummated by September 15, 2022, then Delwinds’ existence will terminate, and Delwinds will distribute amounts in the Trust Account as provided in Delwinds’ Current Charter.

RISK FACTORS

You should carefully consider all the following risk factors, together with all of the other information included or incorporated by reference in this joint proxy statement/consent solicitation statement/prospectus, including the financial information, before deciding whether or how to vote or instruct your vote to be cast to approve the proposals described in this joint proxy statement/consent solicitation statement/prospectus.

The value of your investment following consummation of the Business Combination will be subject to significant risks affecting, among other things, the Combined Company’s business, financial condition or results of operations. If any of the events described below occur, the Combined Company’s post-Business Combination business and financial results could be adversely affected in material respects. This could result in a decline, which may be significant, in the trading price of the Combined Company’s securities and you therefore may lose all or part of your investment. The risk factors described below are not necessarily exhaustive and you are encouraged to perform your own investigation with respect to the businesses of Delwinds and FOXO. Any reference in this “Risk Factors” section to the “surviving entity” shall mean the Combined Company.

Risks Related to the Business Combination

The ability of Delwinds stockholders to exercise redemption rights with respect to a large number of Public Shares or other factors may not allow Delwinds to complete the Business Combination or optimize its capital structure.

If the NTA Proposal is not approved by the Delwinds stockholders, or if a larger number of shares are submitted for redemption than Delwinds currently expects and such redemptions or other conditions are determined to result in a failure to satisfy the net tangible asset requirement set forth in Delwinds’ Current Charter, Delwinds may need to seek to restructure the transaction to reserve a greater portion of the cash in the Trust Account or arrange for third-party financing. Third-party financing may not be available to Delwinds. Furthermore, raising additional third-party financing may involve dilutive equity issuances or the incurrence of indebtedness at higher than desirable levels.

If the Business Combination is unsuccessful, you would not receive your pro rata portion of the Trust Account until Delwinds liquidates the Trust Account or consummates an alternative initial business combination or upon the occurrence of an Extension or certain other corporation actions as set forth in the Current Charter. If you are in need of immediate liquidity, you could attempt to sell your stock in the open market; however, at such time Delwinds’ stock may trade at a discount to the pro rata amount per share in the Trust Account or there may be limited market demand at such time. In either situation, you may suffer a material loss on your investment or lose the benefit of funds expected in connection with Delwinds’ redemption until Delwinds liquidates, consummates an alternative initial business combination, effectuates an Extension or takes certain other actions set forth in the Current Charter or you are able to sell your stock in the open market.

You may be unable to ascertain the merits or risks of FOXO’s operations.

If the Business Combination is consummated, the Combined Company will be affected by numerous risks inherent in the lines of business that FOXO expects to pursue. Although Delwinds’ management has endeavored to evaluate the risks inherent in the proposed Business Combination with FOXO, Delwinds cannot assure you that it can adequately ascertain or assess all of the significant risk factors. Furthermore, some of these risks may be outside of Delwinds’ control. Delwinds also cannot assure you that an investment in Delwinds’ securities will not ultimately prove to be less favorable to investors in Delwinds than a direct investment, if an opportunity were available, in FOXO. In addition, if Delwinds stockholders do not believe that the prospects for the Business Combination are promising, a greater number of stockholders may exercise their redemption rights, which may make it difficult for Delwinds to consummate the Business Combination.

There is no assurance that Delwinds’ diligence will reveal all material risks that may be present with regard to FOXO. Subsequent to the completion of the Business Combination, the Combined Company may be required to take write-downs or write-offs, restructuring and impairment or other charges that could have a significant negative effect on its financial condition and its share price, which could cause you to lose some or all of your investment.

Delwinds cannot assure you that the due diligence Delwinds has conducted on FOXO will reveal all material issues that may be present with regard to FOXO, or that it would be possible to uncover all material issues through a customary amount of due diligence or that risks outside of Delwinds’ control will not later arise. FOXO is aware that Delwinds must

complete an initial business combination by September 15, 2022. Consequently, FOXO may have obtained leverage over Delwinds, knowing that if Delwinds does not complete the Business Combination, Delwinds may be unlikely to be able to complete an initial business combination with any other target business prior to such deadline. In addition, Delwinds has had limited time to conduct due diligence. FOXO is a privately held company that expects to offer products and services that have not yet been fully developed or been commercialized and Delwinds therefore has made its decision to pursue a business combination with FOXO on the basis of limited information, which may result in a business combination that is not as profitable as expected, if at all. As a result of these factors, the Combined Company may be forced to later write-down or write-off assets, restructure operations, or incur impairment or other charges that could result in reporting losses. Even if Delwinds’ due diligence successfully identified certain risks, unexpected risks may arise and previously known risks may materialize in a manner not consistent with our preliminary risk analysis. Even though these charges may be non-cash items and would not have an immediate impact on Delwinds’ liquidity, the fact that Delwinds reports charges of this nature could contribute to negative market perceptions about Delwinds or Delwinds’ securities. In addition, charges of this nature may cause Delwinds to violate leverage or other covenants to which it may be subject as a result of assuming pre-existing debt held by FOXO or by virtue of it obtaining debt financing following the Closing. Accordingly, any stockholders of Delwinds who choose to remain stockholders of the Combined Company following the Business Combination could suffer a reduction in the value of their shares. Such stockholders are unlikely to have a remedy for such reduction in value unless they are able to successfully claim that the reduction was due to the breach by Delwinds’ officers or directors of a duty of care or other fiduciary duty owed by them to Delwinds, or if they are able to successfully bring a private claim under securities laws that the joint proxy statement/consent solicitation statement/prospectus relating to the Business Combination contained an actionable material misstatement or material omission.

RBCCM, one of Delwinds’ IPO Underwriters and financial advisors, and DB, FOXO’s financial advisor, were to be compensated in connection with the Business Combination. RBCCM and DB resigned, waived such compensation and disclaimed any responsibility for this joint proxy statement/consent solicitation statement/prospectus.

On June 1, 2022, RBCCM delivered notice (the “RBCCM Termination Letter”) of the RBCCM Resignation, effective as of June 8, 2022, and waived any fees and compensation in connection with its role as a financial advisor and capital markets advisor to Delwinds. The RBCCM Termination Letter also provided a waiver of RBCCM’s entitlement to the payment of any Deferred UW Fee (in an aggregate amount of $4,021,875) in connection with its role as underwriter in Delwinds’ IPO. RBCCM has informed Delwinds that RBCCM is not responsible for any portion of this joint proxy statement/consent solicitation statement/prospectus which forms a part of this registration statement. RBCCM’s (i) Deferred UW Fee was agreed between Delwinds and the IPO Underwriters in the Underwriting Agreement and (ii) financial advisory fee (the “RBCCM Advisory Fee,” and together with RBCCM’s portion of the Deferred UW Fee, the “RBCCM Fees”) was agreed upon pursuant to an engagement letter of the parties, dated February 24, 2022 (the “Engagement Letter”) and the payment of the RBCCM Fees were conditioned upon closing of the Business Combination.

On June 16, 2022, DB delivered notice (the “DB Resignation Letter”) of DB’s resignation. Pursuant to the DB Resignation Letter, DB resigned from its role as financial advisor to FOXO in connection with the Business Combination and waived all rights to any fees and compensation in connection with such roles, and FOXO mutually accepted this resignation. All such fees and compensation were only payable to DB upon completion of the Business Combination. In addition, DB delivered notice of resignation to the SEC.

As a result of the RBCCM Resignation and the DB Resignation, and the associated waivers of fees, the transactions fees payable by Delwinds and FOXO at the consummation of the Business Combination will be reduced by approximately $12.6 million. The IPO underwriting services being provided by RBCCM and the financial advisory services being provided by RBCCM and DB prior to such resignations were substantially complete at the time of its resignation, with any fees payable to RBCCM and DB for such services contingent upon the Closing of the Business Combination.

We believe that the resignation of RBCCM and DB, and the waiver of fees for services that have already been substantially rendered or that were contingent upon the occurrence of an event that applicable persons expect will occur, is unusual. While RBCCM and DB did not provide any additional detail in their termination letters, stockholders should be aware that such resignations indicate that neither RBCCM nor DB wants to be associated with the disclosures in this proxy statement/prospectus or the underlying business analysis related to the transaction described herein. Neither Delwinds nor FOXO will speculate about the reasons why RBCCM and DB withdrew from their roles as a financial advisor in connection with the Business Combination and forfeited fees after performing substantially all the work to earn such fees. Accordingly, stockholders should not place any reliance on the fact that RBCCM and DB have been previously involved with this transaction.

There are risks to Delwinds stockholders who are not affiliates of the Sponsor of becoming stockholders of the Combined Company through the Business Combination rather than acquiring securities of FOXO directly in an underwritten public offering, including no independent due diligence review by an underwriter.

Because there is no independent third-party underwriter involved in the Business Combination or the issuance of Delwinds’ securities in connection therewith, investors will not receive the benefit of any outside independent review of Delwinds’ and FOXO’s respective finances and operations. Underwritten public offerings of securities conducted by a licensed broker-dealer are subjected to a due diligence review by the underwriter or dealer manager to satisfy statutory duties under the Securities Act, the rules of Financial Industry Regulatory Authority, Inc. (“FINRA”) and the national securities exchange where such securities are listed. Additionally, underwriters or dealer-managers conducting such public offerings are subject to liability for any material misstatements or omissions in a registration statement filed in connection with the public offering. As no such review will be conducted in connection with the Business Combination, Delwinds stockholders must rely on the information in this joint proxy statement/consent solicitation statement/prospectus and will not have the benefit of an independent review and investigation of the type normally performed by an independent underwriter in a public securities offering.

If FOXO became a public company through an underwritten public offering, the underwriters would be subject to liability under Section 11 of the Securities Act for material misstatements and omissions in the initial public offering registration statement. In general, an underwriter is able to avoid liability under Section 11 if it can prove that, it “had, after reasonable investigation, reasonable ground to believe and did believe, at the time . . . the registration statement became effective, that the statements therein (other than the audited financial statements) were true and that there was no omission to state a material fact required to be stated therein or necessary to make the statements therein not misleading.” In order to fulfill its duty to conduct a “reasonable investigation,” an underwriter will, in addition to conducting a significant amount of due diligence on its own, usually require that an issuer’s independent registered public accounting firm provide a comfort letter with respect to certain numbers included in the registration statement and will require the law firm for the issuer to include in its legal opinion to the underwriters a statement that such counsel is not aware of any material misstatements or omissions in the initial public offering registration statement (“Counsel Negative Assurance Statements”). Auditor comfort letters and Counsel Negative Assurance Statements are generally not required in connection with private companies going public through a merger with a special purpose acquisition company, such as Delwinds, and no auditor comfort letters or Counsel Negative Assurance Statements have been requested or obtained in connection with the Business Combination or the preparation of this joint proxy statement/consent solicitation statement/prospectus.

In addition, the amount of due diligence conducted by Delwinds and its advisors in connection with the Business Combination may not be as high as would have been undertaken by an underwriter in connection with an initial public offering of FOXO. Accordingly, it is possible that defects in FOXO’s business or problems with FOXO’s management that would have been discovered if FOXO conducted an underwritten public offering will not be discovered in connection with the Business Combination, which could adversely affect the market price of the Common Stock.

Unlike an underwritten initial public offering, the initial trading of the Combined Company’s securities will not benefit from the book-building process undertaken by underwriters that helps to inform efficient price discovery with respect to opening trades of newly listed shares and underwriter support to help stabilize, maintain or affect the public price of the new issue immediately after listing. The lack of such a process in connection with the listing of the Combined Company’s securities on the NYSE could result in diminished investor demand, inefficiencies in pricing and a more volatile public price for the Combined Company’s securities during the period immediately following the listing.

As described in “The Business Combination Agreement — Resignation of Certain Financial Advisors”, RBCCM has resigned from its role as Delwinds’ financial advisor and capital markets advisor, and has informed Delwinds that RBCCM waives the deferred portion of the underwriting fees to which RBCCM would otherwise have been entitled in connection with the Business Combination under the Underwriting Agreement dated December 10, 2020, entered into at the time of Delwinds’ initial public offering by Delwinds and its IPO Underwriters, including RBCCM, and effective June 16, 2022, DB has resigned from its roles as financial advisor to FOXO in connection with the Business Combination.

The unaudited pro forma financial information included in the section entitled “Unaudited Pro Forma Condensed Combined Financial Statements” may not be representative of the Combined Company’s results if the Business Combination is consummated and accordingly, you will have limited financial information on which to evaluate the financial performance of the Combined Company and your investment decision.

Delwinds and FOXO currently operate as separate companies. Delwinds has had no prior history as an operating company and its operations have not previously been managed on a combined basis. The pro forma financial information is presented for informational purposes only and is not necessarily indicative of the financial position or results of operations that would have actually occurred had the Business Combination been completed at or as of the dates indicated, nor is it indicative of the future operating results or financial position of the Combined Company. The pro forma statement of operations does not reflect future nonrecurring charges resulting from the Business Combination. The unaudited pro forma financial information does not reflect future events that may occur after the Business Combination and does not consider potential impacts of current market conditions on revenues or expenses. The pro forma financial information included in the section entitled “Unaudited Pro Forma Condensed Combined Financial Statements” has been derived from Delwinds’ and FOXO’s historical financial statements and certain adjustments and assumptions have been made regarding the Combined Company after giving effect to the Business Combination. Differences between preliminary estimates in the pro forma financial information and the final acquisition accounting will occur and could have an adverse impact on the pro forma financial information and the Combined Company’s financial position and future results of operations.

In addition, the assumptions used in preparing the pro forma financial information may not prove to be accurate and other factors may affect the Combined Company’s financial condition or results of operations following the Closing. Any potential decline in the Combined Company’s financial condition or results of operations may cause significant variations in the stock price of the Combined Company.

Delwinds may issue additional shares of common or preferred stock to complete the Business Combination which would dilute the interest of Delwinds stockholders and likely present other risks.

The Current Charter authorizes the issuance of up to 43,000,000 shares of Delwinds Class A common stock, 7,000,000 shares of Delwinds Class B common stock, and 1,000,000 shares of preferred stock, par value $0.0001 per share. There are currently 22,242,500 authorized but unissued shares of Delwinds Class A common stock available for issuance, which amount does not take into account shares reserved for issuance upon exercise of outstanding warrants. There are currently 1,968,750 authorized but unissued shares of Delwinds Class B common stock available for issuance. There are currently no shares of preferred stock issued and outstanding. Delwinds may issue a substantial number of additional shares of common or preferred stock to complete the initial business combination or under an employee incentive plan after completion of the Business Combination. However, the Current Charter provides, among other things, that prior to Delwinds’ initial business combination, Delwinds may not issue additional shares of capital stock that would entitle the holders thereof to (i) receive funds from the Trust Account or (ii) vote on any initial business combination. These provisions of the Current Charter, like all other provisions thereof, may be amended with a stockholder vote. Delwinds’ executive officers and directors have agreed, pursuant to a written agreement with Delwinds, that they will not propose any amendment to the Current Charter that would affect the substance or timing of Delwinds’ obligation to redeem 100% of its public shares if Delwinds does not complete the initial business combination by September 15, 2022 (or such other date as approved by the Delwinds stockholders), unless Delwinds provides its public stockholders with the opportunity to redeem their shares of Class A common stock upon approval of any such amendment at a per-share price, payable in cash, equal to the aggregate amount then on deposit in the Trust Account, including interest (which interest shall be net of taxes payable and working capital released to Delwinds), divided by the number of then outstanding public shares. The issuance of additional shares of common or preferred stock:

•        may significantly dilute the equity interest of existing investors;

•        may subordinate the rights of holders of common stock if preferred stock is issued with rights senior to those afforded the Delwinds common stock;

•        could cause a change in control if a substantial number of common stock is issued, which may affect, among other things, Delwinds’ ability to use its net operating loss carry forwards, if any, and could result in the resignation or removal of Delwinds’ present officers and directors; and

•        may adversely affect prevailing market prices for Delwinds’ Units, Class A common stock and/or Warrants.

Delwinds is dependent upon its executive officers and directors and their departure could adversely affect Delwinds’ ability to operate and to consummate the initial business combination. Additionally, Delwinds’ executive officers and directors also allocate their time to other businesses, thereby causing potential conflicts of interest that could have a negative impact on Delwinds’ ability to complete the initial business combination.

Delwinds’ operations and its ability to consummate the Business Combination are dependent upon a relatively small group of individuals and, in particular, its executive officers and directors. Delwinds believes that its success depends on the continued service of its executive officers and directors, at least until the completion of the Business Combination. Delwinds does not have an employment agreement with, or key-man insurance on the life of, any of its directors or executive officers. The unexpected loss of the services of one or more of Delwinds’ directors or executive officers could have a detrimental effect on Delwinds and the ability to consummate the Business Combination. In addition, Delwinds’ executive officers and directors are not required to commit any specified amount of time to its affairs and, accordingly, will have conflicts of interest in allocating management time among various business activities, including monitoring the due diligence and undertaking the other actions required in order to consummate the Business Combination. Each of Delwinds’ executive officers is engaged in several other business endeavors for which they may be entitled to substantial compensation and Delwinds’ directors also serve as officers and board members for other entities. If Delwinds’ executive officers’ and directors’ other business affairs require them to devote substantial amounts of time to such affairs in excess of their current commitment levels, it could limit their ability to devote time to Delwinds’ affairs which may have a negative impact on Delwinds’ ability to consummate the Business Combination.

The Combined Company’s ability to be successful following the Business Combination will depend upon the efforts of the Combined Company Board and key personnel and the loss of such persons could negatively impact the operations and profitability of the Combined Company’s post-Business Combination business.

The Combined Company’s ability to be successful following the Business Combination will be dependent upon the efforts of the Combined Company Board and key personnel. Delwinds cannot assure you that the Combined Company Board and key personnel will be effective or successful or remain with the Combined Company. In addition to the other challenges they will face, such individuals may be unfamiliar with the requirements of operating a public company, which could cause the Combined Company’s management to have to expend time and resources helping them become familiar with such requirements.

It is estimated that, pursuant to the Merger Agreement, Delwinds’ public stockholders will own approximately 26.5% of the equity interests or assets of the Combined Company (assuming no redemptions) and Delwinds’ management, other than Andrew Poole, who is expected to serve on the Combined Company Board, will not be engaged in the management of the Combined Company’s business. Accordingly, the future performance of the Combined Company will depend upon the quality of the post-Business Combination board of directors, management and key personnel of the Combined Company.

Delwinds’ key personnel may negotiate employment or consulting agreements with the Combined Company in connection with the Business Combination. These agreements may provide for them to receive compensation following the Business Combination and as a result, may cause them to have conflicts of interest in determining whether the Business Combination is advantageous.

Delwinds’ key personnel may be able to remain with the Combined Company after the completion of the Business Combination only if they are able to negotiate employment or consulting agreements in connection with the Business Combination. Such negotiations may take place prior to the consummation of the Business Combination and could provide for such individuals to receive compensation in the form of cash payments and/or securities of the Combined Company for services they would render to the Combined Company after the completion of the Business Combination. The personal and financial interests of such individuals may influence their motivation in connection with the consummation of the Business Combination. However, Delwinds believes the ability of such individuals to remain with the Combined Company after the completion of the Business Combination will not be the determining factor in Delwinds’ decisions regarding the consummation of the Business Combination. There is no certainty, however, that any of Delwinds’ key personnel will remain with the Combined Company after the consummation of the Business Combination. Delwinds cannot assure you that any of its key personnel will remain in senior management or advisory positions with the Combined Company.

Because Delwinds’ initial stockholders, executive officers and directors will lose their entire investment in Delwinds if the Business Combination or an alternative business combination is not completed, and because Delwinds’ Sponsor, executive officers and directors will not be eligible to be reimbursed for their out-of-pocket expenses if the Business Combination is not completed, a conflict of interest may have arisen in determining whether FOXO was appropriate for Delwinds’ initial business combination.

Delwinds’ initial stockholders currently own 5,031,250 shares of Class B Common Stock. In addition, the Sponsor purchased an aggregate of 632,500 Placement Units, each consisting of one share of Delwinds Class A common stock and one-half of one Warrant, with each whole Warrant entitling the holder thereof to purchase one share of Delwinds Class A common stock for $11.50 per share, that will also be worthless if Delwinds does not complete a business combination. The Founder Shares are identical to the shares of Class A common stock. However, the initial stockholders have agreed (A) to vote any shares owned by them in favor of any proposed business combination and (B) not to redeem any shares in connection with a stockholder vote to approve a proposed initial business combination.

The personal and financial interests of Delwinds’ executive officers and directors may have influenced their motivation in identifying and selecting a target business combination, completing an initial business combination and influencing the operation of the business following the initial business combination. At the closing of Delwinds’ initial business combination, its Sponsor, executive officers and directors, or any of their respective affiliates, will be reimbursed for any out-of-pocket expenses incurred in connection with activities on Delwinds’ behalf such as identifying potential target businesses and performing due diligence on suitable business combinations. In the event the Business Combination or an alternative business combination is completed, there is no cap or ceiling on the reimbursement of out-of-pocket expenses incurred in connection with activities on Delwinds’ behalf. However, Delwinds’ Sponsor, executive officers and directors, or any of their respective affiliates will not be eligible for any such reimbursement if the Business Combination or an alternative business combination is not completed. Such financial interests of Delwinds’ Sponsor, executive officers and directors may have influenced their motivation in approving the Business Combination and may influence their motivation for completing the Business Combination.

Some of the Delwinds and FOXO officers and directors may be argued to have conflicts of interest that may influence them to support or approve the Business Combination without regard to your interests.

Certain officers and directors of Delwinds and FOXO participate in arrangements that provide them with interests in the Business Combination that may be different from yours, including, among others, the continued service as an officer or director of the Combined Company, severance benefits, equity grants, continued indemnification and the potential ability to sell an increased number of shares of common stock of the Combined Company. If the Business Combination is not consummated and Delwinds is forced to wind up, dissolve and liquidate in accordance with the Current Charter, the 5,031,250 shares of Class B common stock currently held by the Sponsor and Delwinds’ directors and officers, which were initially acquired prior to the IPO by the initial stockholders for an aggregate purchase price of $25,000, will be worthless (as the holders have waived liquidation rights with respect to such shares). Such shares of Class A common stock had an aggregate market value of approximately $50.7 million based on the last sale price of $10.08 per share on the NYSE on August 19, 2022. Accordingly, the Sponsor and Delwinds’ current executive officers and directors, have interests that may be different from, or in addition to, your interests as a stockholder.

These interests, among others, may influence the officers and directors of Delwinds and FOXO to support or approve the Business Combination. For more information concerning the interests of Delwinds and FOXO executive officers and directors, see the sections entitled “The Delwinds Business Combination Proposal — Interests of Delwinds’ Directors and Officers in the Business Combination” and “The FOXO Business Combination Proposal — Interests of FOXO Directors and Executive Officers in the Business Combination” in this joint proxy statement/consent solicitation statement/prospectus.

The value of the Founder Shares following completion of the Business Combination is likely to be substantially higher than the nominal price paid for them, even if the trading price of the Combined Company common stock at such time is substantially less than $10.00 per share.

The Sponsor has invested in Delwinds an aggregate of $6,350,000, comprised of the $25,000 purchase price for the Founder Shares and the $6,325,000 purchase price for the Private Units. Assuming a trading price of $10.00 per share upon consummation of the Business Combination, the 5,031,250 Founder Shares would have an aggregate implied value of $50,312,500. Even if the trading price of the Combined Company common stock were as low as

approximately $1.26 per share, and the Placement Warrants were worthless, the value of the Founder Shares would be equal to the Sponsor’s initial investment in Delwinds. As a result, the Sponsor is likely to be able to recoup its investment in the Combined Company and make a substantial profit on that investment, even if the public shares have lost significant value. Accordingly, the Delwinds management team, which owns interests in the Sponsor, may have an economic incentive that differs from that of the public stockholders to pursue and consummate the Business Combination rather than to liquidate and to return all of the cash in the trust to the public stockholders. For the foregoing reasons, you should consider the Delwinds management team’s financial incentive to complete the Business Combination when evaluating whether to redeem your shares prior to or in connection with the Business Combination.

Delwinds stockholders and FOXO’s stockholders may not realize a benefit from the Business Combination commensurate with the ownership dilution they will experience in connection with the Business Combination.

If the Combined Company is unable to realize the full strategic and financial benefits currently anticipated from the Business Combination, Delwinds stockholders and FOXO’s stockholders will have experienced substantial dilution of their ownership interests in their respective companies without receiving any commensurate benefit, or only receiving part of the commensurate benefit to the extent the Combined Company is able to realize only part of the strategic and financial benefits currently anticipated from the Business Combination.

During the pendency of the Business Combination, Delwinds and FOXO may not be able to enter into a business combination with another party because of restrictions in the Merger Agreement, which could adversely affect their respective businesses. Furthermore, certain provisions of the Merger Agreement may discourage third parties from submitting alternative takeover proposals, including proposals that may be superior to the arrangements contemplated by the Merger Agreement.

Covenants in the Merger Agreement impede the ability of Delwinds and FOXO to make acquisitions or complete other transactions that are not in the ordinary course of business pending completion of the Business Combination. As a result, if the Business Combination is not completed, the parties may be at a disadvantage to their competitors during that period. In addition, while the Merger Agreement is in effect, each party is generally prohibited from soliciting, initiating, encouraging or entering into certain extraordinary transactions, such as a merger, sale of assets or other business combination outside the ordinary course of business, with any third party. Any such transactions could be favorable to such party’s stockholders.

If the conditions to the Merger are not met, the Business Combination may not occur.

Even if the Business Combination is approved by the stockholders of Delwinds (including each of the Required Approvals) and FOXO, specified conditions must be satisfied or waived to complete the Business Combination. These conditions are described in detail in the Merger Agreement and in addition to stockholder consent, include among other requirements, (i) receipt of requisite regulatory approvals and no law or order preventing the transactions, (ii) no pending litigation to enjoin or restrict the Closing, (iii) each party’s representations and warranties being true and correct as of the date of the Merger Agreement and as of the Closing (subject to Material Adverse Effect), (iv) each party complying in all material respects with its covenants and agreements, (v) no Material Adverse Effect with respect to a party since the date of the Merger Agreement which remains continuing and uncured, (vi) the members of the post-Closing board being elected or appointed, (vii) an effective registration statement and (viii) the conditional NYSE approval. See “Business Combination Proposal (Proposal 2) — Conditions to the Closing” below for a more complete summary. Delwinds and FOXO cannot assure you that all of the conditions will be satisfied. If the conditions are not satisfied or waived, the Business Combination may not occur, or may be delayed and such delay may cause Delwinds and FOXO to each lose some or all of the intended benefits of the Business Combination. If the Business Combination does not occur, Delwinds may not be able to find another potential candidate for its initial business combination prior to Delwinds’ deadline (currently September 15, 2022), and Delwinds will be required to liquidate.

Specifically as to regulatory approvals, FOXO indirectly owns and controls FOXO Life Insurance Company, an Arkansas domestic stock life insurer, and upon the consummation of the Business Combination, Delwinds will directly own and control FOXO. Therefore, Delwinds will acquire indirect control of FOXO Life Insurance Company upon consummation of the Business Combination. Acquisition of control of an Arkansas domestic insurer requires, under Arkansas insurance laws, the prior approval of the Arkansas Insurance Commissioner. Delwinds has filed a Form A Statement Regarding the Acquisition of Control of a Domestic Insurer (“Form A”) with the Arkansas Insurance Commissioner applying for approval of Delwinds’ acquisition of control of FOXO Life Insurance Company.

While Delwinds expects that the Arkansas Insurance Commissioner will issue an order approving Delwinds’ acquisition of control of FOXO Life Insurance Company, there can be no assurance that such approval will be obtained, nor that it will be obtained in time to consummate the Business Combination within the time period contemplated by Merger Agreement. Further, if the Arkansas Insurance Commissioner determines that the Arkansas Insurance Commissioner will approve the acquisition of control of FOXO Life Insurance Company by Delwinds only upon certain conditions, there can be no certainty that Delwinds would find such conditions acceptable or would be able to satisfy such conditions. Any delay or failure to obtain the Arkansas Insurance Commissioner’s approval of the acquisition of control of FOXO Life Insurance Company could prevent the Business Combination from being consummated or being delayed.

We may be subject to U.S. foreign investment regulations which may impose conditions on or limit certain investors’ ability to purchase our securities or otherwise participate in the Business Combination, potentially making the securities less attractive to investors. Our future investments in U.S. companies may also be subject to U.S. foreign investment regulations.

Delwinds’ sponsor, DIAC Sponsor LLC (the “Sponsor”), is a Delaware limited liability company, which is not controlled by, and does not have substantial ties to, any non-U.S. person. Andrew J. Poole, Delwinds’ Chief Executive Officer and Chairman, a U.S. citizen, is the sole managing member of the Sponsor. Neither Mr. Poole nor, to the best of Delwinds’ knowledge, any other member of the Sponsor is controlled by, or has any substantial ties to, any non-U.S. person. To the best of FOXO’s knowledge, there are no officers, directors or stockholders involved in the transaction that is, is controlled by, or has substantial ties with a non-U.S. person.

The Committee on Foreign Investment in the U.S. (“CFIUS”) is an interagency committee authorized to review certain transactions involving acquisitions and investments in the U.S. by foreign persons in order to determine the effect of such transactions on the national security of the U.S. CFIUS has jurisdiction to review transactions that could result in control of a U.S. business directly or indirectly by a foreign person, certain non-controlling investments that afford the foreign investor non-passive rights in a “TID U.S. business” (defined as a U.S. business that (1) produces, designs, tests, manufactures, fabricates, or develops one or more critical technologies; (2) owns or operates certain critical infrastructure; or (3) collects or maintains directly or indirectly sensitive personal data of U.S. citizens), and certain acquisitions, leases, and concessions involving real estate even with no underlying U.S. business. Certain categories of acquisitions of and investments in a U.S. business also may be subject to a mandatory notification requirement.

If CFIUS considers Delwinds a “foreign person” under such rules and regulations and FOXO a U.S. business that may affect national security, we could be subject to such foreign ownership restrictions and/or CFIUS review. If the Business Combination with FOXO falls within the scope of foreign ownership restrictions, we may be unable to consummate the Business Combination. In addition, if the Business Combination falls within CFIUS’s jurisdiction, we may be required to make a mandatory filing or determine to submit a voluntary notice to CFIUS, or to proceed with the Business Combination without notifying CFIUS and risk CFIUS intervention, before or after closing the initial business combination. Although we do not believe Delwinds is a “foreign person” or FOXO is a U.S. business that may affect national security, CFIUS may take a different view and decide to block or delay the Business Combination, impose conditions to mitigate national security concerns with respect to the Business Combination, order us to divest all or a portion of a U.S. business of the Combined Company if we had proceeded without first obtaining CFIUS clearance, or impose penalties if CFIUS believes that the mandatory notification requirement applied. The foreign ownership limitations, and the potential impact of CFIUS, may prevent us from consummating the Business Combination with FOXO.

Moreover, the process of government review, whether by CFIUS or otherwise, could be lengthy. Because we have only a limited time to complete the Business Combination, our failure to obtain any required approvals within the requisite time period may require us to liquidate. If we liquidate, our public shareholders may only receive approximately $10.12 per Public Share (based on the amount in the Trust Account as of August 19, 2022), and our warrants will expire worthless. This will also cause you to lose any potential investment opportunity in FOXO and the chance of realizing future gains on your investment through any price appreciation in the Combined Company.

In addition, CFIUS could choose to review past or proposed transactions involving new or existing foreign investors in us or in the Sponsor, even if a filing with CFIUS is or was not required at the time of the Business Combination. Any review and approval of an investment or transaction by CFIUS may have outsized impacts on transaction certainty, timing, feasibility, and cost, among other things. CFIUS policies and practices are rapidly evolving, and in the event that CFIUS reviews one or more proposed or existing investment by investors, there can be no assurances that such investors will be able to maintain, or proceed with, such investments on terms acceptable to

such investors. CFIUS could seek to impose limitations or restrictions on, or prohibit, investments by such investors (including, but not limited to, limits on purchasing our stock, limits on information sharing with such investors, requiring a voting trust, governance modifications, or forced divestiture, among other things).

Delaware law and the Combined Company’s certificate of incorporation and bylaws will contain certain provisions, including anti-takeover provisions, that limit the ability of stockholders to take certain actions and could delay or discourage takeover attempts that stockholders may consider favorable.

The Proposed Charter and the Proposed Bylaws that will be in effect upon consummation of the Business Combination, and the DGCL, contain provisions that could have the effect of rendering more difficult, delaying, or preventing an acquisition deemed undesirable by the Combined Company Board and therefore depress the trading price of the Combined Company’s common stock. These provisions could also make it difficult for stockholders to take certain actions, including electing directors who are not nominated by the current members of the FOXO Board or taking other corporate actions, including effecting changes in the management of the Combined Company. Among other things, the Proposed Charter and the Proposed Bylaws include provisions regarding:

•        opting out of Section 203 of the DGCL to allow the Combined Company to establish its own rules governing business combinations with interested parties;

•        the ability of the Combined Company Board to issue shares of preferred stock, including “blank check” preferred stock and to determine the price and other terms of those shares, including preferences and voting rights, without stockholder approval, which could be used to significantly dilute the ownership of a hostile acquirer;

•        the limitation of the liability of, and the indemnification of, the Combined Company’s directors and officers;

•        the exclusive right of the Combined Company Board to elect a director to fill a vacancy created by the expansion of the Combined Company Board or the resignation, death or removal of a director, which prevents stockholders from being able to fill vacancies on the Combined Company Board;

•        the requirement that a special meeting of stockholders may be called only by the Combined Company Board, the chairperson of the Combined Company Board, the Combined Company’s chief executive officer or the Combined Company’s president (in the absence of a chief executive officer), which could delay the ability of stockholders to force consideration of a proposal or to take action, including the removal of directors;

•        controlling the procedures for the conduct and scheduling of board of directors and stockholder meetings;

•        the requirement for the affirmative vote of holders of at least 2/3 of the voting power of all of the then outstanding shares of the voting stock, voting together as a single class, to amend, alter, change or repeal any provision of the Proposed Charter or the Proposed Bylaws, which could preclude stockholders from bringing matters before annual or special meetings of stockholders and delay changes in the Combined Company Board and also may inhibit the ability of an acquirer to effect such amendments to facilitate an unsolicited takeover attempt;

•        the ability of the Combined Company Board to amend the bylaws, which may allow the Combined Company Board to take additional actions to prevent an unsolicited takeover and inhibit the ability of an acquirer to amend the bylaws to facilitate an unsolicited takeover attempt;

•        advance notice procedures with which stockholders must comply to nominate candidates to the Combined Company Board or to propose matters to be acted upon at a stockholders’ meeting, which could preclude stockholders from bringing matters before annual or special meetings of stockholders and delay changes in the Combined Company Board and also may discourage or deter a potential acquirer from conducting a solicitation of proxies to elect the acquirer’s own slate of directors or otherwise attempting to obtain control of the Combined Company; and

•        a Combined Company Board that is divided into three classes, Class I, Class II and Class III, with each class serving staggered terms, which could preclude stockholders from bringing matters before annual or special meetings of stockholders and delay changes in the Combined Company Board and also may discourage or deter a potential acquirer from conducting a solicitation of proxies to elect the acquirer’s own slate of directors or otherwise attempting to obtain control of the Combined Company.

These provisions, alone or together, could delay or prevent hostile takeovers and changes in control or changes in the Combined Company Board or management.

Any provision of the Proposed Charter, the Proposed Bylaws or Delaware law that has the effect of delaying or preventing a change in control could limit the opportunity for stockholders to receive a premium for their shares of the Combined Company’s capital stock and could also affect the price that some investors are willing to pay for the Combined Company’s common stock.

The Proposed Charter will designate a state or federal court located within the State of Delaware as the exclusive forum for substantially all disputes between the Combined Company and its stockholders, and also provide that the federal district courts will be the exclusive forum for resolving any complaint asserting a cause of action arising under the Securities Act, each of which could limit the ability of the Combined Company’s stockholders to choose the judicial forum for disputes with the Combined Company or its directors, officers, or employees.

The Proposed Charter, which will become effective upon the Closing, will provide that, unless the Combined Company consents in writing to the selection of an alternative forum, the sole and exclusive forum for (i) any derivative action or proceeding brought on its behalf, (ii) any action asserting a claim of breach of a fiduciary duty owed by any of its directors, officers, or other employees to the Combined Company or its stockholders, (iii) any action arising pursuant to any provision of the DGCL, or the certificate of incorporation or the bylaws or (iv) any other action asserting a claim that is governed by the internal affairs doctrine shall be the Court of Chancery of the State of Delaware (or, if the Court of Chancery does not have jurisdiction, the federal district court for the District of Delaware), in all cases subject to the court having jurisdiction over indispensable parties named as defendants. The Proposed Charter will also provide that the federal district courts of the United States of America will be the exclusive forum for resolving any complaint asserting a cause of action arising under the Securities Act. The exclusive forum provision will be applicable to the fullest extent permitted by applicable law, subject to certain exceptions. Section 27 of the Exchange Act creates exclusive federal jurisdiction over all suits brought to enforce any duty or liability created by the Exchange Act or the rules and regulations thereunder. As a result, the exclusive forum provision will not apply to suits brought to enforce any duty or liability created by the Exchange Act or any other claim for which the federal courts have exclusive jurisdiction. We note, however, that there is uncertainty as to whether a court would enforce this provision and that investors cannot waive compliance with the federal securities laws and the rules and regulations thereunder. Section 22 of the Securities Act creates concurrent jurisdiction for state and federal courts over all suits brought to enforce any duty or liability created by the Securities Act or the rules and regulations thereunder.

Any person or entity purchasing or otherwise acquiring any interest in any of the Combined Company’s securities shall be deemed to have notice of and consented to this provision. This choice of forum provision may limit a stockholder’s ability to bring a claim in a judicial forum that it finds favorable for disputes with us or our directors, officers or other employees, or could result in increased costs for a stockholder to bring a claim, particularly if they do not reside in or near Delaware, both of which may discourage such lawsuits against us and our directors, officers and employees. Alternatively, if a court were to find these provisions inapplicable to, or unenforceable in respect of, one or more of the specified types of actions or proceedings, the Combined Company may incur additional costs associated with resolving such matters in other jurisdictions, which could adversely affect the Combined Company’s business and financial condition.

The issuances of additional shares of Class A Common Stock under the Cantor Agreement may result in dilution of future Class A Common stockholders and have a negative impact on the market price of the Class A Common Stock.

We believe that the proceeds from the Business Combination and our existing cash and cash equivalents are able to meet the working capital needs of the Combined Company. Our estimates may prove to be inaccurate, and we could spend our capital resources faster than we currently expect. Further, changing circumstances, some of which may be beyond our control, could cause us to spend capital significantly faster than we currently anticipate, and we may need to seek additional funding sooner than planned, including drawdowns under the Cantor Agreement. To the extent this occurs, it could impose significant dilution on the stockholders of the combined entity.

The Combined Company is entitled to sell shares of Class A Common Stock for gross proceeds of an aggregate of up to $40 million to the Cantor Investor, at a price equal to 97% of the volume weighted average price of the Class A Common Stock during the applicable trading date on which the Combined Company has timely delivered notice to the Cantor Investor directing it to purchase the shares of Class A Common Stock, subject to meeting the terms and conditions of the Cantor Agreement. This equity line facility is available after the Closing for a period until the first day of the month next following the 36-month anniversary of when the SEC has declared effective a registration statement covering the resale of such shares of Class A Common Stock or until the date on which the facility has been fully utilized, if earlier. The limitations on the amount and frequency of the draws that the Combined Company can

make under the Cantor Agreement, which include (i) the requirement that there be an effective registration statement covering the resale of the shares of Class A Common Stock to be issued under the Cantor Agreement and (ii) offering size restrictions relating to the Combined Company’s trading volume, which may affect its ability to draw under the Cantor Agreement. Therefore, the proceeds under the Cantor Agreement may be less than anticipated.

In addition, the closing of the Business Combination would entitle the Cantor Investor to receive payment of a commitment fee of $1.6 million payable in shares of Class A Common Stock.

The issuances of Class A Common Stock pursuant to the Cantor Agreement would result in dilution of future Class A Common stockholders and could have a negative impact on the market price of the Class A Common Stock and the Combined Company’s ability to obtain additional financing.

The Sponsor, directors, officers, advisors and their affiliates may elect to purchase Delwinds Class A common stock or the Public Warrants from Delwinds public stockholders, which may influence a vote on a proposed initial business combination and reduce the public “float” of the Delwinds Class A common stock.

The Sponsor, directors, officers, advisors or their affiliates may purchase shares of Delwinds Class A common stock or the Public Warrants or a combination thereof in privately negotiated transactions or in the open market either prior to or following the completion of the Business Combination, although they are under no obligation to do so. However, other than as expressly stated herein, they have no current commitments, plans or intentions to engage in such transactions and have not formulated any terms or conditions for any such transactions. None of the funds in the Trust Account will be used to purchase shares of Delwinds Class A common stock or the Public Warrants in such transactions.

Such a purchase may include a contractual acknowledgement that such stockholder, although still the record holder of our shares, is no longer the beneficial owner thereof and therefore agrees not to exercise its redemption rights. In the event that the Sponsor, directors, officers, advisors or their affiliates purchase shares of Delwinds Class A common stock in privately negotiated transactions from Delwinds public stockholders who have already elected to exercise their redemption rights, such selling stockholders would be required to revoke their prior elections to redeem their shares. The purpose of such purchases could be to vote such shares in favor of the initial business combination and thereby increase the likelihood of obtaining stockholder approval of the initial business combination. Any such purchases of the Delwinds securities may result in the completion of our initial business combination that may not otherwise have been possible. Any such purchases will be reported pursuant to Section 13 and Section 16 of the Exchange Act to the extent such purchasers are subject to such reporting requirements.

In addition, if such purchases are made, the public “float” of Delwinds Class A common stock or the Public Warrants and the number of beneficial holders of our securities may be reduced, possibly making it difficult to obtain or maintain the quotation, listing or trading of the Delwinds securities on a national securities exchange.

Delwinds Stockholders who redeem their Delwinds Class A Common Stock may continue to hold any Delwinds Public Warrants that they own, which will result in dilution to non-redeeming Delwinds Stockholders upon exercise of such Delwinds Public Warrants or Closing Warrants, as applicable.

Delwinds Stockholders who redeem their Delwinds Class A Common Stock may continue to hold any Delwinds Public Warrants that they own at such time, which will result in additional dilution to non-redeeming holders upon exercise of such warrants. Assuming (a) all redeeming Delwinds Stockholders that acquired Delwinds Units in the Delwinds Initial Public Offering and continue to hold the Delwinds Public Warrants that were included in such Delwinds Units, and (b) maximum redemption of Delwinds Class A Common Stock held by the redeeming Delwinds Stockholders, 10,062,500 Delwinds Public Warrants would be retained by redeeming Delwinds Stockholders. As a result, the redeeming Delwinds Stockholders would hold Delwinds Public Warrants with an aggregate market value of $2.2 million, as of August 19, 2022, while non-redeeming Delwinds Stockholders would suffer dilution in their percentage ownership of the Combined Company upon exercise of the Delwinds Public Warrants held by redeeming Delwinds Stockholders.

Changes in laws or regulations, or a failure to comply with any laws and regulations, may adversely affect Delwinds’ business, including its ability to complete the Business Combination, and results of operations.

Delwinds is subject to laws and regulations enacted by national, regional and local governments. In particular, Delwinds is required to comply with certain SEC and other legal requirements. Compliance with, and monitoring of, applicable laws and regulations may be difficult, time consuming and costly. Those laws and regulations and their interpretation and application may also change from time to time and those changes could have a material adverse

effect on Delwinds’ business, investments and results of operations. In addition, a failure to comply with applicable laws or regulations, as interpreted and applied, could have a material adverse effect on Delwinds’ business, including its ability to complete the Business Combination, and results of operations.

Risks Related to Ownership of Combined Company Common Stock

An active market for the Combined Company’s securities may not develop, which would adversely affect the liquidity and price of the Combined Company’s securities.

The price of the Combined Company’s securities may vary significantly due to factors specific to the Combined Company as well as to general market or economic conditions. Furthermore, an active trading market for the Combined Company’s securities may never develop or, if developed, it may not be sustained. You may be unable to sell your securities unless a market can be established and sustained.

There can be no assurance that the shares of the Combined Company’s common stock that will be issued in connection with the Business Combination will be approved for listing on the NYSE following the Closing, or that the Combined Company will be able to comply with the continued listing rules of the NYSE.

In connection with the Business Combination and as a condition to FOXO’s obligations to complete the Business Combination, the Company will be required to demonstrate compliance with the NYSE’s initial listing requirements, which generally require, among other criteria, a per share price of at least $4.00 and a market capitalization of at least $150,000,000. In addition to the listing requirements for the Combined Company’s common stock, the NYSE imposes listing standards on warrants. Delwinds cannot assure you that the Combined Company will be able to meet those initial listing requirements, in which case FOXO will not be obligated to complete the Business Combination.

In order to continue the listing of its securities on the NYSE, Delwinds prior to the Business Combination, and the Combined Company following the consummation of the Business Combination, must maintain certain financial, share price and, subject to change as a result of recent rule changes proposed by the NYSE, distribution levels. Generally, a listed company must maintain a minimum market capitalization (generally $50,000,000) and a minimum number of holders of its securities (currently 300 public holders). Even if the Combined Company’s common stock and warrants are approved for listing on the NYSE, the Company may not meet the NYSE continued listing requirements following the Business Combination.

If the NYSE delists the Combined Company’s securities from trading on its exchange and the Company is not able to list its securities on another national securities exchange, the Combined Company’s securities could be quoted on an over-the-counter market. If this were to occur, the Combined Company could face significant material adverse consequences, including:

•        a limited availability of market quotations for its securities;

•        reduced liquidity for its securities;

•        a determination that the Combined Company’s common stock is a “penny stock” which will require brokers trading in the common stock to adhere to more stringent rules and possibly result in a reduced level of trading activity in the secondary trading market for the Combined Company’s securities;

•        a decreased ability to issue additional securities or obtain additional financing in the future.

The continued eligibility for listing of FOXO’s securities may depend on, among other things, the number of shares of Delwinds common stock that are redeemed.

The National Securities Markets Improvement Act of 1996, which is a federal statute, prevents or preempts the states from regulating the sale of certain securities, which are referred to as “covered securities.” Because Delwinds’ units, common stock and warrants are listed on the NYSE, Delwinds’ units, common stock and warrants qualify as covered securities under the statute. Although the states are preempted from regulating the sale of Delwinds’ securities, the federal statute does allow the states to investigate companies if there is a suspicion of fraud, and, if there is a finding of fraudulent activity, then the states can regulate or bar the sale of covered securities in a particular case. While Delwinds is not aware of a state having used these powers to prohibit or restrict the sale of securities issued by blank check companies, other than the State of Idaho, certain state securities regulators view blank check companies unfavorably and might use these

powers, or threaten to use these powers, to hinder the sale of securities of blank check companies in their states. Further, if Delwinds was no longer listed on the NYSE, Delwinds’ securities would not qualify as covered securities under the statute and Delwinds would be subject to regulation in each state in which Delwinds offers its securities.

The market price of the Combined Company’s common stock may decline as a result of the Business Combination.

The market price of the Combined Company’s common stock may decline as a result of the Business Combination for a number of reasons including if:

•        investors react negatively to the prospects of the Combined Company’s business and the prospects of the Business Combination;

•        the effect of the Business Combination on the Combined Company’s business and prospects is not consistent with the expectations of financial or industry analysts; or

•        the Combined Company does not achieve the perceived benefits of the Business Combination as rapidly or to the extent anticipated by financial or industry analysts.

The Combined Company’s stock price may change significantly following the Business Combination and you could lose all or part of your investment as a result.

The trading price of the Combined Company common stock is likely to be volatile. The stock market recently has experienced extreme volatility. This volatility often has been unrelated or disproportionate to the operating performance of particular companies. You may not be able to resell your shares of the Combined Company common stock at an attractive price due to a number of factors such as those listed in “— Risks Related to FOXO” and the following:

•        results of operations that vary from the expectations of securities analysts and investors;

•        results of operations that vary from those of the Combined Company’s competitors;

•        changes in expectations as to the Combined Company’s future financial performance, including financial estimates and investment recommendations by securities analysts and investors;

•        declines in the market prices of stocks generally;

•        strategic actions by the Combined Company or its competitors;

•        announcements by the Combined Company or its competitors of significant contracts, acquisitions, joint ventures, other strategic relationships or capital commitments;

•        any significant change in the Combined Company’s management;

•        changes in general economic or market conditions or trends in the Combined Company’s industry or markets;

•        changes in business or regulatory conditions, including new laws or regulations or new interpretations of existing laws or regulations applicable to the Combined Company’s business;

•        future sales of the Combined Company common stock or other securities;

•        investor perceptions of the investment opportunity associated with the Combined Company common stock relative to other investment alternatives;

•        the public’s response to press releases or other public announcements by the Combined Company or third parties, including the Combined Company’s filings with the SEC;

•        litigation involving the Combined Company, the Combined Company’s industry, or both, or investigations by regulators into the Combined Company Board, the Combined Company’s operations or those of the Combined Company’s competitors;

•        guidance, if any, that the Combined Company provides to the public, any changes in this guidance or the Combined Company’s failure to meet this guidance;

•        the development and sustainability of an active trading market for the Combined Company common stock;

•        actions by institutional or activist stockholders;

•        changes in accounting standards, policies, guidelines, interpretations or principles; and

•        other events or factors, including those resulting from pandemics, natural disasters, war, acts of terrorism or responses to these events.

These broad market and industry fluctuations may adversely affect the market price of the Combined Company common stock, regardless of the Combined Company’s actual operating performance. In addition, price volatility may be greater if the public float and trading volume of the Combined Company common stock is low.

In the past, following periods of market volatility, stockholders have instituted securities class action litigation. If the Combined Company was involved in securities litigation, it could have a substantial cost and divert resources and the attention of executive management from the Combined Company’s business regardless of the outcome of such litigation.

Because there are no current plans to pay cash dividends on the Combined Company common stock for the foreseeable future, you may not receive any return on investment unless you sell your Combined Company common stock at a price greater than what you paid for it.

The Combined Company intends to retain future earnings, if any, for future operations, expansion and debt repayment and there are no current plans to pay any cash dividends for the foreseeable future. The declaration, amount and payment of any future dividends on shares of the Combined Company common stock will be at the sole discretion of the Combined Company Board. The Combined Company Board may take into account general and economic conditions, the Combined Company’s financial condition and results of operations, the Combined Company’s available cash and current and anticipated cash needs, capital requirements, contractual, legal, tax and regulatory restrictions, implications of the payment of dividends by the Combined Company to its stockholders or by its subsidiaries to it and such other factors as the Combined Company Board may deem relevant. As a result, you may not receive any return on an investment in the Combined Company common stock unless you sell your Combined Company common stock for a price greater than that which you paid for it.

The Combined Company stockholders may experience dilution in the future.

The percentage of shares of the Combined Company common stock owned by current stockholders may be diluted in the future because of equity issuances for acquisitions, capital market transactions or otherwise, including, without limitation, equity awards that the Combined Company may grant to its directors, officers and employees, or the exercise of the Combined Company warrants. Such issuances may have a dilutive effect on the Combined Company’s earnings per share, which could adversely affect the market price of the Combined Company common stock.

Certain Delwinds warrants are accounted for as a warrant liability and will be recorded at fair value upon issuance with changes in fair value each period reported in earnings, which may have an adverse effect on the market price of the Combined Company common stock.

On April 12, 2021, the SEC Staff issued the SEC Staff Statement, wherein the SEC Staff expressed its view that certain terms and conditions common to SPAC warrants may require the warrants to be classified as liabilities on the SPAC’s balance sheet as opposed to being treated as equity. Specifically, the SEC Staff Statement focused on certain settlement terms and provisions related to certain tender offers following a business combination, which terms are similar to those contained in the warrant agreement governing the Delwinds warrants. In light of the issues raised in the SEC Staff Statement, Delwinds reevaluated the accounting treatment of the Delwinds warrants, and pursuant to the guidance in ASC 815, Derivatives and Hedging (“ASC 815”), determined the Delwinds warrants should be classified as derivative liabilities measured at fair value on our balance sheet, with any changes in fair value to be reported each period in earnings on Delwinds’ statement of operations.

As a result of the recurring fair value measurement, Delwinds’ financial statements may fluctuate quarterly, based on factors that are outside of Delwinds’ control. Due to the recurring fair value measurement, Delwinds expects it will recognize non-cash gains or losses on Delwinds’ warrants each reporting period and that the amount of such gains or losses could be material.

If securities or industry analysts do not publish research or reports about the Combined Company’s business, if they change their recommendations regarding the Combined Company common stock or if the Combined Company’s operating results do not meet their expectations, the Combined Company common stock price and trading volume could decline.

The trading market for the Combined Company common stock will depend in part on the research and reports that securities or industry analysts publish about the Combined Company or its businesses. If no securities or industry analysts commence coverage of the Combined Company, the trading price for the Combined Company common stock could be negatively impacted. In the event securities or industry analysts initiate coverage, if one or more of the analysts who cover the Combined Company downgrade its securities or publish unfavorable research about its businesses, or if the Combined Company’s operating results do not meet analyst expectations, the trading price of the Combined Company common stock would likely decline. If one or more of these analysts cease coverage of the Combined Company or fail to publish reports on the Combined Company regularly, demand for the Combined Company common stock could decrease, which might cause the Combined Company common stock price and trading volume to decline.

Delwinds stockholders will experience immediate dilution as a consequence of the issuance of Common Stock. Having a minority share position may reduce the influence that Delwinds’ current stockholders have on the management of the Combined Company.

It is anticipated that, following the Business Combination (1) Delwinds’ public stockholders are expected to own approximately 26.5% of the outstanding Common Stock, (2) the FOXO Stockholders are expected to collectively own approximately 59.5% of the outstanding Common Stock, and (3) the Sponsor and other initial stockholders are expected to own approximately 13.6% of the outstanding Common Stock.

Future sales, or the perception of future sales, by the Combined Company or its stockholders in the public market following the Business Combination could cause the market price for the Combined Company common stock to decline.

The sale of shares of the Combined Company common stock in the public market, or the perception that such sales could occur, could harm the prevailing market price of shares of the Combined Company common stock. These sales, or the possibility that these sales may occur, also might make it more difficult for the Combined Company to sell equity securities in the future at a time and at a price that it deems appropriate.

Upon consummation of the Business Combination, it is currently expected that the Combined Company will have a total of 41,725,187 shares of the Combined Company common stock outstanding (excluding the exercise of any Assumed Options and Assumed Warrants and assuming that (i) there are no redemptions of any shares by Delwinds’ public stockholders in connection with the Business Combination, and (ii) no awards are issued under the Incentive Plan. All shares currently held by Delwinds public stockholders and all of the shares issued in the Business Combination to existing FOXO securityholders will be freely tradable without registration under the Securities Act, and without restriction by persons other than the Combined Company’s “affiliates” (as defined under Rule 144 under the Securities Act, (“Rule 144”)), including the Combined Company’s directors, executive officers and other affiliates.

Simultaneously with the execution and delivery of the Merger Agreement, certain stockholders of FOXO, who are expected to collectively own approximately 12.1% of the shares of the Combined Company common stock outstanding following the Business Combination (based on the above assumptions and FOXO’s current stockholdings), agreed with Delwinds pursuant to the Lock-Up Agreements, subject to certain exceptions, not to dispose of or hedge any of their shares of the Combined Company common stock or securities convertible into or exchangeable for shares of the Combined Company common stock during the period from the date of the Closing and ending upon the earlier to occur of the 1-year anniversary of the Closing or, if the lock-up period applicable to the Founder Shares is amended in accordance with the Insider Letter Amendment Proposal, upon approval thereof by Delwinds stockholders, 180 days after the Closing (subject to early release if FOXO consummates a liquidation, merger, share exchange or other similar transaction with an unaffiliated third party). Additionally, prior to the Closing, the existing lock-up agreements between FOXO and the 2021 Bridge Investors, who are expected to collectively own approximately 8.4% of the shares of the Combined Company common stock outstanding following the Business Combination (based on the above assumptions and FOXO’s current stockholders), excluding those holders that entered into the Lock-Up Agreements, which lock-up agreements restrict transfers within a six month period after the Closing, shall be amended to join Delwinds and Purchaser Representative as parties thereto. See “The Business Combination Proposal — Related Agreements — Lock-up Agreements.”

In addition, the shares of the Combined Company common stock reserved for future issuance under the Incentive Plan will become eligible for sale in the public market once those shares are issued, subject to any applicable vesting requirements, lockup agreements and other restrictions imposed by law. A total number of shares representing 10% of the fully diluted outstanding shares of the Combined Company common stock immediately following consummation of the Merger are expected to be reserved for future issuance under the Incentive Plan. The Combined Company is expected to file one or more registration statements on Form S-8 under the Securities Act to register shares of the Combined Company common stock or securities convertible into or exchangeable for shares of the Combined Company common stock issued pursuant to the Incentive Plan. Any such Form S-8 registration statements will automatically become effective upon filing. Accordingly, shares registered under such registration statements will be available for sale in the open market.

In the future, the Combined Company may also issue its securities in connection with investments or acquisitions. The amount of shares of the Combined Company common stock issued in connection with an investment or acquisition could constitute a material portion of the then-outstanding shares of the Combined Company common stock. Any issuance of additional securities in connection with investments or acquisitions may result in additional dilution to the Combined Company stockholders.

Delwinds currently is, and the Combined Company will be, an “emerging growth company” within the meaning of the Securities Act, and if the Combined Company takes advantage of certain exemptions from disclosure requirements available to emerging growth companies, this could make our securities less attractive to investors and may make it more difficult to compare our performance with other public companies.

Delwinds is currently and, following the consummation of the Merger, the Combined Company will be, an “emerging growth company” within the meaning of the Securities Act, as modified by the JOBS Act. The Combined Company may continue to take advantage of certain exemptions from various reporting requirements that are applicable to other public companies that are not emerging growth companies including, but not limited to, not being required to comply with the auditor attestation requirements of Section 404 of the Sarbanes-Oxley Act, reduced disclosure obligations regarding executive compensation in periodic reports and proxy statements, and exemptions from the requirements of holding a nonbinding advisory vote on executive compensation and stockholder approval of any golden parachute payments not previously approved. As a result, the Combined Company stockholders may not have access to certain information they may deem important. We cannot predict whether investors will find securities issued by the Combined Company less attractive because the Combined Company will rely on these exemptions. If some investors find those securities less attractive as a result of its reliance on these exemptions, the trading prices of the Combined Company’s securities may be lower than they otherwise would be, there may be a less active trading market for the Combined Company’s securities and the trading prices of the Combined Company’s securities may be more volatile.

Further, Section 102(b)(1) of the JOBS Act exempts emerging growth companies from being required to comply with new or revised financial accounting standards until private companies (that is, those that have not had a Securities Act registration statement declared effective or do not have a class of securities registered under the Exchange Act) are required to comply with the new or revised financial accounting standards. The JOBS Act provides that a company can elect to opt out of the extended transition period and comply with the requirements that apply to non-emerging growth companies but any such election to opt out is irrevocable. Delwinds has elected not to opt out of such extended transition period, which means that when a standard is issued or revised and it has different application dates for public or private companies, the Combined Company, as an emerging growth company, can adopt the new or revised standard at the time private companies adopt the new or revised standard. This may make comparison of the Combined Company’s financial statements with another public company that is neither an emerging growth company nor an emerging growth company that has opted out of using the extended transition period difficult or impossible because of the potential differences in accounting standards used.

The Combined Company will remain an emerging growth company until the earliest of: (i) the last day of the fiscal year following the fifth anniversary of the closing of the IPO, (ii) the last day of the fiscal year in which the Combined Company has total annual gross revenue of at least $1.07 billion; (iii) the last day of the fiscal year in which the Combined Company is deemed to be a “large accelerated filer” as defined in Rule 12b-2 under the Exchange Act, which would occur if the market value of the Combined Company common stock held by non-affiliates exceeded $700.0 million as of the last business day of the second fiscal quarter of such year; or (iv) the date on which the Combined Company has issued more than $1.0 billion in non-convertible debt securities during the prior three-year period.

The Combined Company may redeem unexpired Public Warrants prior to their exercise at a time that is disadvantageous for warrant holders.

The Combined Company will have the ability to redeem outstanding Public Warrants at any time after they become exercisable and prior to their expiration, at a price of $0.01 per warrant, provided that the last reported sales price of the Combined Company common stock equals or exceeds $18.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within a 30 trading-day period ending on the third trading day prior to the date the Combined Company sends the notice of redemption to the warrant holders. If and when the Public Warrants become redeemable by the Combined Company, the Combined Company may exercise its redemption right if there is a current registration statement in effect with respect to the shares of the Combined Company common stock underlying such warrants. Redemption of the outstanding Public Warrants could force you to: (i) exercise your warrants and pay the related exercise price at a time when it may be disadvantageous for you to do so; (ii) sell your warrants at the then-current market price when you might otherwise wish to hold your warrants; or (iii) accept the nominal redemption price which, at the time the outstanding Public Warrants are called for redemption, is likely to be substantially less than the market value of your warrants. None of the Private Warrants will be redeemable by the Combined Company for cash so long as they are held by the Sponsor or its permitted transferees.

In the event the Combined Company determines to redeem the Public Warrants, holders of our redeemable warrants would be notified of such redemption as described in our warrant agreement. Specifically, in the event that the Company elects to redeem all of the redeemable warrants as described above, the Company will fix a date for the redemption (the “Redemption Date”). Notice of redemption will be mailed by first class mail, postage prepaid, by the Combined Company not less than 30 days prior to the Redemption Date to the registered holders of the redeemable warrants to be redeemed at their last addresses as they appear on the registration books. Any notice mailed in the manner provided in the warrant agreement will be conclusively presumed to have been duly given whether or not the registered holder received such notice. In addition, beneficial owners of the redeemable warrants will be notified of such redemption via the Combined Company’s posting of the redemption notice to DTC. The closing price for the Delwinds Class A Common Stock as of August 19, 2022 was $10.08 and has never exceeded the $18.00 threshold that would trigger the right to redeem the Public Warrants following the Closing.

Risks Related to Redemption

There is no guarantee that a Delwinds public stockholder’s decision whether to redeem its shares of Delwinds common stock for a pro rata portion of the Trust Account will put such stockholder in a better future economic position.

We cannot assure you as to the price at which a public stockholder may be able to sell the shares of the Combined Company common stock in the future following the completion of the Business Combination. Certain events following the consummation of any business combination, including the Merger, may cause an increase in the Combined Company stock price, and may result in a lower value realized now than a Delwinds stockholder might realize in the future had the stockholder not elected to redeem such stockholder’s public shares. Similarly, if a Delwinds public stockholder does not redeem such stockholder’s shares, such stockholder will bear the risk of ownership of the Combined Company common stock after the consummation of the Business Combination, and there can be no assurance that a stockholder can sell such stockholder’s shares of the Combined Company common stock in the future for a greater amount than the redemption price set forth in this joint proxy statement/consent solicitation statement/prospectus. A Delwinds public stockholder should consult such stockholder’s own tax or financial advisor for assistance on how this may affect its individual situation.

If Delwinds public stockholders fail to comply with the redemption requirements specified in this joint proxy statement/consent solicitation statement/prospectus, they will not be entitled to redeem their public shares for a pro rata portion of the funds held in the Trust Account.

Delwinds intends to comply with the U.S. federal proxy rules in conducting redemptions in connection with the Business Combination. However, despite Delwinds’ compliance with these rules, if a Delwinds stockholder fails to receive Delwinds’ proxy materials, such stockholder may not become aware of the opportunity to redeem its shares of Delwinds common stock. In addition, this joint proxy statement/consent solicitation statement/prospectus provides the various procedures that must be complied with in order to validly tender or redeem public shares. In the event that a public stockholder fails to comply with these or any other procedures, its public shares may not be redeemed.

In order to exercise their redemption rights, public stockholders are required to deliver their public shares, either physically or electronically using The Depository Trust Company’s DWAC System, to Delwinds’ transfer agent prior to the vote at the Delwinds Special Meeting. If a public stockholder properly seeks redemption as described in this joint proxy statement/consent solicitation statement/prospectus and the Business Combination is consummated, Delwinds will redeem these public shares for a pro rata portion of the funds deposited in the Trust Account and the public stockholder will no longer own such public shares following the Merger. See the section entitled “Delwinds Special Meeting of Stockholders — Redemption Rights” for additional information on how to exercise your redemption rights.

If you or a “group” of Delwinds stockholders of which you are a part is deemed to hold an aggregate of more than 15% of the public shares, you (or, if a member of such a group, or all of the members of such group in the aggregate) will lose the ability to redeem all such public shares in excess of 15% of the public shares.

A public stockholder, together with any of such stockholder’s affiliates or any other person with whom it is acting in concert or as a “group” (as defined in Section 13(d)(3) of the Exchange Act), will be restricted from redeeming in the aggregate such stockholder’s public shares or, if part of such a group, the group’s public shares, in excess of 15% of the public shares, without the prior consent of Delwinds. However, Delwinds stockholders’ ability to vote all of their public shares (including such excess shares) for or against the Business Combination Proposal is not restricted by this limitation on redemptions. Your inability to redeem any such excess public shares could result in you suffering a material loss on your investment in Delwinds if you sell such excess public shares in open market transactions. Delwinds cannot assure you that the value of such excess public shares will appreciate over time following the Business Combination or that the market price of the public shares will exceed the per share redemption price.

Risk Related to FOXO

Unless the context otherwise requires, references to “we,” “us” and “our” in this subsection “— Risks Related to FOXO” generally refer to FOXO in the present tense and the Combined Company from and after the Business Combination.

Risks Related to FOXO’s Business and Industry

FOXO has a history of losses and it may not achieve or maintain profitability in the future.

FOXO is a development stage company and has not been profitable since its inception in 2019, accumulating deficits of $87,882,000, $51,976,000 and $13,488,000 as of June 30, 2022, December 31, 2021 and December 31, 2020, respectively. FOXO incurred net losses of $38,488,000 and $8,653,000 in the years ended December 31, 2021 and December 31, 2020, respectively, and $35,906,000 for the six months ended June 30, 2022. FOXO expects it will require significant capital in connection with its efforts to commence commercial operations following consummation of the Business Combination, and it will be required to continue to make significant investments to further develop and expand its business. In particular, it expects to continue to expend substantial financial and other resources on marketing and advertising as part of its strategy to develop and increase its brand awareness, customer base, as well as on research and development activities regarding its epigenetic biomarker technology. The brand awareness marketing and advertising expenses that FOXO will incur will typically be expensed immediately. In addition, FOXO expects to continue to increase its headcount significantly in the coming years. As a public company, FOXO expects to incur significant legal, accounting and other expenses that it did not incur as a private company. FOXO expects that its net loss will increase in the near term as it continues to make such investments to grow its business. Despite these investments, FOXO may not succeed in increasing its revenue on the timeline that it expects or in an amount sufficient to lower its net loss and ultimately become profitable. Moreover, if FOXO’s revenue declines, it may not be able to reduce costs in a timely manner because many of its costs are fixed, at least in the short term. In addition, if FOXO reduces variable costs to respond to losses, this may limit its ability to enter into agreements with new customers and grow its revenues. Accordingly, FOXO may not achieve or maintain profitability and it may continue to incur significant losses in the future.

FOXO’s independent registered public accounting firms have included an explanatory paragraph relating to FOXO’s ability to continue as a going concern in its report on FOXO’s audited financial statements included in this joint proxy statement/consent solicitation statement/prospectus, which could limit FOXO’s ability to raise additional capital and thereby materially adversely impact its business.

FOXO’s audited financial statements for the years ended December 31, 2021 and 2020 were prepared assuming that it will continue as a going concern. Primarily as a result of FOXO’s losses, limited working capital, convertible debt obligations and significant operating costs expected to be incurred in the next twelve months, the reports of FOXO’s independent registered public accounting firms included elsewhere in this joint proxy statement/consent solicitation statement/prospectus

contain an explanatory paragraph on its financial statements stating there is substantial doubt about its ability to continue as a going concern. Such an opinion could materially limit FOXO’s ability to raise additional funds through the issuance of new debt or equity securities or otherwise. There is no assurance that sufficient financing will be available when needed to allow FOXO to continue as a going concern. The perception that FOXO may not be able to continue as a going concern may also make it more difficult to operate its business due to concerns about its ability to meet its contractual obligations.

If FOXO is unable to secure additional capital, it may be required to curtail its business initiatives and take additional measures to reduce costs in order to conserve its cash in amounts sufficient to sustain operations and meet its obligations. These measures could cause a significant reduction in the scope of FOXO’s planned development, which could harm its business, financial condition and operating results. It is not possible for FOXO to predict at this time the potential success of its business. The revenue and income potential of FOXO’s proposed business and operations are currently unknown. The accompanying financial statements do not include any adjustments that may be necessary should FOXO be unable to continue as a going concern.

FOXO will require additional capital to commercialize its product and service offerings and grow its business, which may not be available on terms acceptable to it or at all.

To the extent that FOXO’s present capital and the proceeds that FOXO may receive from the Business Combination and related financing transactions is insufficient to meet operating requirements (including regulatory capital requirements) or to cover losses, FOXO will need to raise additional funds through financings to carry out its business plans. Many factors will affect FOXO’s capital needs as well as their amount and timing, including FOXO’s growth and profitability as well as market disruptions and other developments.

Historically, FOXO has funded its operations, marketing expenditures and capital expenditures primarily through equity issuances and debt instruments. FOXO evaluates financing opportunities from time-to-time, and its ability to obtain financing will depend, among other things, on its development efforts, business plans and operating performance, and the condition of the capital markets at the time it seeks financing. FOXO cannot be certain that additional financing will be available to it on favorable terms, or at all.

If FOXO raises additional funds through the issuance of equity, equity-linked or debt securities, its existing stockholders may experience dilution. Any debt financing secured by FOXO in the future could require that a substantial portion of its operating cash flow be devoted to the payment of interest and principal on such indebtedness, which may decrease available funds for other business activities, and could involve restrictive covenants relating to its capital-raising activities and other financial and operational matters, which may make it more difficult for FOXO to obtain additional capital and to pursue business opportunities.

If FOXO is unable to obtain adequate financing or financing on terms satisfactory to it, FOXO’s ability to continue to support its business growth, maintain minimum amounts of risk-based capital and to respond to business challenges could be significantly limited, and its business, results of operations and financial condition could be adversely impacted.

FOXO’s future success depends in large part on the continued participation in the business of Jon Sabes, FOXO’s founder and Chief Executive Officer of the Combined Company, which cannot be ensured or guaranteed.

Jon Sabes, FOXO’s founder and Chief Executive Officer, and member of its board of directors, is expected to serve as a member of the board of directors, and the Chief Executive Officer, of the Combined Company after consummation of the Business Combination. Since inception, Mr. Sabes has been instrumental in shaping FOXO’s vision, strategic direction and execution priorities. There can be no assurance that Mr. Sabes will continue to work for FOXO or that he will continue to serve as an officer or director of the Combined Company. Mr. Sabes’ departure from service with the Combined Company could materially adversely impact FOXO’s business.

The loss of the services of FOXO’s other current executives or other key employees, or the failure to attract additional key individuals, could materially adversely impact its business, results of operations and financial condition.

FOXO’s financial success is dependent to a significant degree upon the efforts of its current executive officers and other key employees. At present, FOXO does not maintain key-man life insurance policies for any of these individuals. In addition, FOXO’s success and viability will depend to a significant extent upon its ability to attract and retain qualified personnel in all areas of its business, especially its sales, science, and financial management teams. If FOXO were to lose the key members of its respective teams, it would need to replace them with qualified individuals in a timely manner or its business, results of operations and financial condition could be adversely impacted.

FOXO’s business significantly depends upon the strength of its brands, and if it is not able to develop, maintain and enhance its brands, its ability to develop and expand its customer base may be adversely impacted and its business and operating results may be harmed.

FOXO believes that the brand identity it will develop (encompassing multiple brands) will significantly contribute to the success of its business. Developing, maintaining and enhancing its brands may require FOXO to make substantial investments and these investments may not be successful. If FOXO fails to develop, maintain or enhance its brands, or if it incurs excessive expenses in this effort, its business, operating results and financial condition may be materially adversely impacted. Many of FOXO’s competitors have brands that are well recognized. As a relatively new entrant into the markets in which it operates, FOXO will likely spend considerable money and other resources to create brand awareness and build its reputation. FOXO anticipates that, as its market becomes increasingly competitive, maintaining and enhancing its brands may become increasingly difficult and expensive.

FOXO may not be able to build brand awareness, and its efforts at building, maintaining and enhancing its reputation could fail. Complaints or negative publicity about FOXO’s business practices, its marketing and advertising campaigns, its compliance with applicable laws and regulations, the integrity of the data that it provides to consumers or business partners, data privacy and security issues, and other aspects of its business, whether valid or not, could diminish confidence in FOXO’s brands, which could adversely impact its reputation and business. FOXO’s management team, including its Chief Executive Officer and other executive officers, could be subject to negative publicity that could interfere with FOXO’s ability to successfully establish its brand or impact FOXO’s ability to compete for business or attract and retain customers.

FOXO was formed to become a separate and independently managed and controlled entity from GWG Holdings, Inc. (“GWG”). GWG, which remains a significant stockholder in FOXO, on April 20, 2022, announced that it has filed for chapter 11 bankruptcy protection in the Federal Bankruptcy Court for the Southern District of Texas. FOXO’s Chief Executive Officer was an officer and director of GWG prior to the formation of FOXO in November 11, 2019. FOXO is not a party to this bankruptcy and FOXO’s Chief Executive Officer has not been an officer or director of GWG since April 2019, but the bankruptcy proceedings could negatively impact the brand of FOXO and its Chief Executive Officer.

As FOXO commercializes and expands its product offerings and enters new markets, it needs to establish its reputation with customers, and to the extent that it is not successful in creating positive impressions, its business could be adversely impacted. There can be no assurance that FOXO will be able to develop, maintain or enhance its reputation, and failure to do so could materially adversely impact its business, results of operations and financial condition. If FOXO is unable to develop, maintain or enhance consumer awareness of its brands in a cost-effective manner, its business, results of operations and financial condition could be materially adversely impacted.

Members of FOXO’s management team have been, and may from time to time be, associated with negative media coverage or become involved in legal or regulatory proceedings or investigations unrelated to FOXO’s business.

Members of our management team have been involved in a wide variety of businesses, including transactions, such as sales and purchases of businesses, and ongoing operations. As a result of such involvement, members of our management team may from time to time be associated with negative media coverage or become involved in legal or regulatory proceedings or investigations unrelated to FOXO’s business. For example, Jon Sabes, FOXO’s CEO and member of the FOXO Board, was the chief executive officer and director of GWG until April 26, 2019. On April 20, 2022, GWG, which is a significant stockholder in FOXO, announced that it filed for chapter 11 bankruptcy protection in the Federal Bankruptcy Court for the Southern District of Texas. In addition, GWG previously disclosed that it received a subpoena from the SEC’s Division of Enforcement on October 6, 2020 to produce documents in connection with an investigation related to its investment products and accounting matters. Any negative media coverage, regulatory proceedings or investigations related to FOXO’s management team, may be detrimental to the management team’s reputation or result in other negative consequences or damages, which could cause a material adverse impact on FOXO’s business and the stock price of the Combined Company.

Development of new products and services will require substantial resources, and FOXO cannot guarantee that it will have the resources or ability to continue such development.

Developing new products and services requires substantial technical, financial and human resources, whether or not any products or services are ultimately commercialized. FOXO may pursue what it believes is a promising opportunity only to discover that certain of its risk or resource allocation decisions were incorrect or insufficient, or that

individual products, services or its science in general has technology limitations or risks that were previously unknown or underappreciated. In the event material decisions in any of these areas turn out to be incorrect or sub-optimal, FOXO may experience a material adverse impact on its business and ability to fund its operations.

FOXO’s success is based on its ability to integrate molecular biotechnology into the life insurance industry, and its inability to do so may adversely affect its operating results, business prospects and its ability to repay its obligations.

The success of FOXO’s business is based upon its ability to create new products and services by integrating molecular biotechnology into the life insurance industry. FOXO expects that current and future developments in molecular biotechnology will enhance the life insurance industry; however, the industry’s acceptance of molecular biotechnology will primarily be impacted by a variety of factors such as the acceptance of new products and services by consumers, insurance carriers, and agents; as well as the interpretation of existing laws and regulations (including laws relating to privacy), the passage of new legislation and regulations, interest rates, reserve requirements and actuarial understandings and methodologies, and future innovations in molecular biotechnology. Importantly, the factors that FOXO believes will most significantly affect the development and success of its products and services in the life insurance industry are beyond its control. Any material and adverse development in the life insurance market could adversely affect FOXO’s operating results, its access to capital, and its business prospects and viability. Because of this, an investment in the common stock of the Combined Company generally involves greater risk as compared to investments offered by companies with more diversified business operations in more established markets.

FOXO’s success depends, in large part, on its ability to commercialize its technology enabled products and services with a high level of service at a competitive price, achieve sufficient sales volume to realize economies of scale, and create innovative new products and services to offer to its customers. FOXO’s failure to achieve any of these outcomes would adversely impact its business.

FOXO’s success depends, in large part, on its ability to extend its technology enabled products and services to the life insurance market with a high level of service at a competitive price, achieve sufficient sales volume to realize economies of scale, and create innovative new products and services to offer to its customers. The growth and expansion of FOXO’s business and service offerings, once such offerings are commercialized, is expected to place a continuous significant strain on FOXO’s management, operational and financial resources. To effectively manage its growth following development and commercialization of its products and services, FOXO must continue to implement and improve its operational, financial and management information systems and to expand, train and manage its employee base. While FOXO plans to partner with third-party commercialization partners, as well as one or more domestic and/or international insurance carriers, it must continue to work to scale its own operations to meet increases in demand for FOXO’s products and services. In the event of further growth of its operations or in the number of its third-party relationships, FOXO’s supply, systems, procedures or internal controls may not be adequate to support its operations and its management may not be able to manage any such growth effectively.

Even if FOXO is able to successfully scale its infrastructure and operations, it cannot ensure that demand for its products and services will increase at levels consistent with the growth of its infrastructure. If FOXO fails to generate demand commensurate with this growth or if it fails to scale its infrastructure sufficiently in advance to meet such demand, its business, financial condition and results of operations could be materially adversely impacted.

FOXO expects its revenue and results of operations to fluctuate on a quarterly and annual basis.

FOXO’s revenue and results of operations could vary significantly from period-to-period and may fail to match expectations as a result of a variety of factors, some of which are outside of its control. Among other factors, FOXO’s revenue and results may vary as a result of fluctuations in the number of customers purchasing insurance products from FOXO or its business partners, research and development expenditures, and/or the timing and amount of its expenses. Fluctuations and variability across the industry may affect FOXO’s revenue and results of operations. As a result of the potential variations in its revenue and results of operations, period-to-period comparisons may not be meaningful and the results of any one period should not be relied on as an indication of future performance. In addition, FOXO’s results of operations may not meet the expectations of investors or public market analysts who follow the Combined Company, which may adversely impact its stock price.

FOXO’s success and the growth of its business will depend on its ability to effectively and in a cost-feasible manner acquire, maintain, and engage with its targeted customers. If FOXO fails to acquire, maintain, and engage customers, its business, revenue, operating results and financial condition will be adversely impacted.

As a new company, FOXO anticipates that sales and marketing expenses will continue to represent a large part of its overall operating costs for the foreseeable future. FOXO cannot guarantee, however, that its investments in sales and marketing will effectively reach potential customers, potential customers will decide to buy its products or services, or that customer spend for its products and services will yield the intended return on investment.

In addition, many factors, some of which are beyond FOXO’s control, may reduce its ability to acquire, maintain and engage with customers, including the following:

•        potential customers in a particular marketplace or generally do not meet FOXO’s underwriting guidelines;

•        FOXO’s competitors mimic its digital platform, causing current and potential customers to purchase their insurance products instead of FOXO’s products;

•        changes in advertising platforms’ pricing, which could result in higher advertising costs, and changes in digital advertising platforms’ policies, that may delay or prevent FOXO from advertising through these channels;

•        changes in search algorithms by search engines;

•        ineffectiveness of FOXO’s marketing efforts and other spend to acquire new customers;

•        decline in popularity of, or governmental restrictions on, social media platforms where FOXO plans to advertise;

•        the development of new search engines or social media sites that reduce traffic on existing search engines and social media sites;

•        FOXO suffering reputational harm to its brand resulting from negative publicity, whether accurate or inaccurate;

•        FOXO failing to expand geographically;

•        FOXO failing to obtain an insurance license in jurisdictions where a license is sought;

•        FOXO failing to offer new and competitive products;

•        FOXO failing to develop effective distribution systems;

•        technical or other problems frustrate the customer experience, particularly if those problems prevent FOXO from generating quotes or paying claims in a fast and reliable manner;

•        FOXO is unable to address customer concerns regarding the content, privacy and security; or

•        consumer behavior changes as a result of the COVID-19 pandemic.

FOXO’s inability to overcome these challenges could adversely impact its ability to attract and add new customers, as well as retain existing customers, once obtained, and could have an adverse effect on FOXO’s business, revenue, operating results and financial condition. Further, if FOXO’s customer base does not grow, it may be required to incur significantly higher marketing expenses than it currently anticipates in order to attract new customers. A significant decline in its customer base could have a materially adverse impact on its business, financial condition and results of operations.

Security incidents or real or perceived errors, failures, or bugs in FOXO’s systems or websites could adversely impact its operations, result in loss of personal customer information, damage its reputation and brand, and harm its business and operating results.

FOXO’s success, in particular the sale of insurance products through the FOXO Life brand, will be dependent on its systems, applications, and software operating and meeting the changing needs of FOXO’s customers and users. FOXO will rely on its technology and vendors to successfully implement changes to and maintain its systems and services in an efficient and secure manner. Like all information systems and technology, FOXO’s websites may contain material errors, failures, vulnerabilities or bugs, particularly when new features or capabilities are released, and may be subject to computer viruses or malicious code, break-ins, phishing impersonation attacks, attempts to overload its

servers with denial-of-service or other attacks, ransomware and similar incidents or disruptions from unauthorized use of its computer systems, as well as unintentional incidents causing data leakage, any of which could lead to interruptions, delays or website or online app shutdowns, or could cause loss of critical data, or the unauthorized disclosure, access, acquisition, alteration or use of personal or other confidential information.

If FOXO experiences compromises to its security that result in technology performance, integrity, or availability problems, the complete shutdown of its websites or the loss or unauthorized disclosure, access, acquisition, alteration or use of confidential information, customers or potential customers may lose trust and confidence in FOXO, and may decrease the use of its systems or websites, or stop using its systems or websites entirely. Further, outside parties may attempt to fraudulently induce employees or customers to disclose sensitive information in order to gain access to FOXO’s information, including customer information. Because the techniques used to obtain unauthorized access, disable or degrade service, or sabotage systems change frequently, they are often not recognized until launched against a target, and may originate from less regulated and remote areas around the world, FOXO may be unable to proactively address these techniques or to implement adequate preventative measures. Even if FOXO takes steps that it believes are adequate to protect it from cyber threats, hacking against its competitors or other companies could create the perception among its customers or potential customers that its systems or websites are not safe to use.

A significant impact on the performance, reliability, security, and availability of FOXO’s systems, software, or services may harm its reputation, impair its ability to operate, retain customers or attract new customers for the FOXO or FOXO Life brands, and expose FOXO to legal claims and government action, each of which could have a material adverse impact on its business, results of operations, and financial condition.

Changes in general economic conditions could have a material adverse impact on FOXO’s business.

Changes in general economic conditions, including, for example, interest rates, investor sentiment, changes specifically affecting the insurance industry, biotechnology industry, competition, technological developments, political and diplomatic events, tax laws, and other factors not known to FOXO today, could substantially and materially adversely impact FOXO’s business. For example, changes in interest rates may increase its cost of capital and ability to raise capital, and have a corresponding adverse impact on its operating results. While FOXO may engage in certain hedging activities to mitigate the impact of these changes, none of these conditions are or will be within its control. Changes in general economic conditions may also negatively impact demand for life insurance and FOXO’s other products and services.

FOXO’s business may be adversely impacted by the continuation of the COVID-19 pandemic.

In 2020, the global COVID-19 pandemic spread to every country and every state in the United States. The World Health Organization designated COVID-19 as a pandemic, and numerous countries, including the United States, declared national emergencies with respect to the COVID-19 pandemic. While vaccines have been approved and are slowly being deployed, the global impact of the outbreak continues to adversely affect many industries, and different geographies continue to reflect the effects of public health restrictions in various ways. The timing and likelihood of achieving widespread global vaccination remain uncertain, and these vaccines may be less effective against new variants, potentially leading people to continue to self-isolate and not participate in the economy at pre-pandemic levels for a prolonged period of time.

The economic recovery following the impact of the COVID-19 pandemic is only partially underway and has been gradual, uneven and characterized by meaningful dispersion across sectors and regions with uncertainty regarding its ultimate length and trajectory. Further, although many jurisdictions had relaxed or lifted restrictions in an effort to generate more economic activity, the risk of continued COVID-19 outbreaks remains, and some jurisdictions may re-impose restrictions in an effort to mitigate risks to public health, especially as more infectious variants of the virus emerge. Increasing infection rates and hospitalizations in certain geographies and a potential resulting market downturn may have a negative impact on FOXO’s planned products and services as well as the business of third parties on which it may rely, and as a result could materially adversely impact FOXO’s business, results of operations and financial condition. It is also possible that the global recovery from the COVID-19 pandemic may reduce demand for personal life insurance and FOXO’s other products and services.

These and other potential impacts make it more challenging for management to estimate the future performance of FOXO’s business. While FOXO cannot predict the specific impacts to its business, financial condition and results of operations, the impacts could be materially negative. These impacts will depend on future developments, which are highly uncertain and out of its control, including, among others, the duration and intensity of the COVID-19 pandemic, as well

as the subsequent resumption of business operations and recovery of discretionary consumer spending across the globe. Additional impacts may arise that FOXO is not aware of currently. The potential of such additional impacts intensifies the business and operating risks that FOXO faces, and should be considered when reading the additional risk factors below.

FOXO plans to expand operations abroad, through planned relationships with international life insurance carriers, where FOXO has limited operating experience and where FOXO may be subject to increased regulatory risks and local competition. If FOXO is unsuccessful in any efforts to expand internationally, its business may be harmed.

Regulations exist or are under consideration in countries outside the United States, which limit or prevent the sale of direct-to-consumer genetic tests. Some countries, including Australia, require premarket review by their regulatory body similar to that required in the United States by the FDA. Some countries, including Australia, Germany, France and Switzerland, require a physician prescription for genetic tests providing health information, thus limiting its offering in those countries to an ancestry-only test. Other countries require mandatory genetic counseling prior to genetic testing. If similar prohibitions were enacted with respect to epigenetic testing, or the scope of the aforementioned regulations were expanded to include epigenetics, it could limit the available market for FOXO’s products and services and increase the costs associated with marketing the products and services where FOXO is able to offer its products.

FOXO’s also plans to expand its life insurance business internationally, which will subject it to additional laws and regulatory standards with respect to the insurance business and insurance distribution. FOXO has no previous experience in operating its life insurance business internationally, may incur significant operating expenses in connection, and may not be successful in its compliance with such international laws and regulations.

Legal developments in the European Union have created a range of new compliance obligations regarding transfers of personal data from the European Union to the United States, including the GDPR and UK GDPR, which may apply to certain of FOXO’s activities related to services that it offers or may offer to individuals located in the European Union. Significant effort and expense will be required to ensure compliance with the GDPR and UK GDPR, and could cause FOXO to change its business practices. Moreover, requirements under the GDPR and UK GDPR may change periodically or may be modified by the European Union or the UK and/or the laws of one or more countries. The GDPR and UK GDPR impose stringent compliance obligations regarding the handling of personal data and have resulted in the issuance of significant financial penalties for noncompliance, including possible fines of up to 4% of global annual turnover for the preceding financial year or €20 million/£17.5 million (whichever is higher) for the most serious violations.

FOXO may also need to achieve and maintain International Standards Organization (or ISO) certification of its future Quality Management Systems. If FOXO is not able to achieve or maintain regulatory compliance, it may not be permitted to market its insurance products and/or may be subject to enforcement by EU Competent Authorities, bodies with authority to act on behalf of the government of the applicable EU Member State, or other nations which adopt similar standards, to ensure that the requirements of the directive or regulation are met.

If FOXO fails to comply with any applicable laws and regulations, it may not be able to expand internationally or could become subject to enforcement actions or the imposition of significant monetary fines, other penalties, or claims, which could harm its ability to conduct its business and could have a material adverse impact on its business, financial condition and results of operations.

Risks Related to FOXO’s Epigenetic Testing Services

FOXO’s success and ability to establish and grow its epigenetic testing services will depend on developing epigenetic biomarkers for use in life insurance underwriting. If FOXO fails to develop epigenetic biomarkers that attract and retain life insurance carriers as customers, its operating results and financial condition will be adversely affected.

FOXO is still in the process of developing its saliva-based epigenetic biomarkers for use in life insurance underwriting. If its efforts to develop saliva-based epigenetic biomarkers for health and wellness conditions used in life insurance underwriting fail, FOXO’s ability to attract customers for its underwriting technology services will be adversely impacted.

FOXO’s ability to attract and add new insurance or reinsurance carriers as customers, as well as retain existing customers, once obtained, depends, in large part, on the ability of its epigenetic biomarkers to provide accurate, cost-effective information for life insurance underwriting. If life insurance carriers or reinsurance carriers do not perceive FOXO’s underwriting technology services to be reliable and of high quality, if it fails to introduce new and improved products and services, or if it introduces new products or services that are not favorably received by the market, FOXO

may not be able to attract or retain customers. In order for its epigenetic biomarkers technology to provide and continue to provide actuarial value, FOXO may be required to incur significantly higher research and development expenses, costs related to improving its services, and lower margins in order to attract new customers and retain existing customers.

While FOXO will strive to demonstrate the actuarial value of epigenetic biomarker technology it is developing to insurance companies, reinsurers, underwriters, and insurance agents, these counterparts may not embrace its underwriting technology services. Moreover, if FOXO fails to remain competitive on pricing and actuarial accuracy, its ability to grow its business and generate revenue by attracting and retaining customers may be adversely impacted.

Many factors, some of which are beyond FOXO’s control, may reduce its ability to sell its underwriting technology services, including those described in this “Risk Factors” section and the following:

•        FOXO’s potential carrier customers or regulators not understanding or appreciating its science or results (including lack of understanding of the difference between genetics and epigenetics);

•        FOXO’s competitors offering alternative underwriting solutions;

•        FOXO suffering reputational harm to its brand resulting from negative publicity, whether accurate or inaccurate;

•        FOXO failing to offer price competitive products and services;

•        FOXO experiencing technical or other problems that inhibit its ability to service carrier customers in a fast and reliable manner;

•        FOXO being unable to address regulatory concerns regarding the application of epigenetic biomarkers for use in life insurance underwriting;

•        FOXO experiencing regulatory changes that make epigenetics unavailable for use in life insurance underwriting;

•        FOXO being unable to address customer concerns regarding content, privacy and security; or

•        FOXO being impacted by consumer behavior changes as a result of the COVID-19 pandemic.

FOXO’s inability to overcome these challenges could adversely impact its ability to execute its underwriting technology services business and could have an adverse effect on its business, revenue, operating results and financial condition. The inability to commercialize FOXO’s underwriting technology services business would have a materially adverse impact on its business, financial condition and results of operations.

FOXO is applying the relatively new field of epigenetics to life insurance underwriting, which it cannot guarantee will produce the results it seeks or needs for its business model.

While the scientific field of epigenetics and its importance in gene expression is well understood, the scientific field is still developing and the concept of obtaining individually predictive biomarkers of health and wellness from saliva is novel. Most epigenetic research to date has been conducted from blood specimens and has produced extensive peer reviewed publications on the association between DNA methylation and health and wellness factors associated with life insurance underwriting (i.e., tobacco use, cardiovascular health, metabolic health, alcohol use, and drugs of abuse). These association studies, while informative, differ from the individually predictive epigenetic biomarkers FOXO develops and requires for use in life insurance underwriting. In addition, these peer reviewed association studies have not published extensive research on DNA methylation derived from saliva. Accordingly, while FOXO believes that individually predictive biomarkers are available in saliva at accuracy levels that are actuarially significant for use in life insurance underwriting, it cannot guarantee the accuracy of such epigenetic biomarkers, and any errors in the accuracy or results provided by such biomarkers could hinder its ability to gain market share in a very competitive industry. If FOXO is unable to obtain individually predictive epigenetic biomarkers in saliva at accuracy levels efficacious for life insurance underwriting, or if the epigenetic biomarkers do not perform as expected, it could significantly affect its ability to generate revenue from such product, which could then result in a complete loss of your investment.

FOXO’s 2019 Pilot Study demonstrated that epigenetic biomarkers are available in both blood and saliva for traditional life insurance underwriting risk factors, but further research may not validate or improve the results discovered in the Pilot Study.

In 2019, FOXO completed a Pilot Study that sought to measure a wide range of health and wellness factors used in traditional life insurance underwriting with DNA methylation data derived from blood and saliva (see “Information About FOXO — Epigenetic Biomarkers” and “Information About FOXO — Insurance Services Platforms: FOXO Labs — Commercialization of Saliva-Based Epigenetic Biomarkers”).While the Pilot Study was able to identify patterns of DNA methylation (i.e., epigenetic biomarkers) of individuals that correlated with clinical health and wellness measurements used in standard life insurance underwriting, FOXO cannot guarantee that the results of the Pilot Study are completely accurate, or that the results of the Pilot Study will be further validated or improved upon in follow-on research which could negatively impact its ability to pursue its business plans and generate revenue.

FOXO currently has research projects planned and underway designed to further discover, improve and validate the use of its epigenetic biomarkers for its planned commercial purposes, but it cannot guarantee the results of such research and any negative results may negatively impact its ability to pursue its business plans.

FOXO’s current and planned research projects are designed to further discover, improve and validate the use of epigenetic biomarkers for commercial use in life insurance underwriting. The main research projects FOXO has underway are the Physicians’ Health Study, the Validation Study, and the Parallel Run Study (see “Information About FOXO — Insurance Services Platform: FOXO Labs — Research and Development of Epigenetic Biomarkers”).

In addition to the Physicians’ Health Study, the Validation Study and the Parallel Run Study research projects, FOXO has several additional research projects underway that target specific epigenetic biomarkers such as “drugs of abuse” (see “Information About FOXO — Insurance Services Platform: FOXO Labs — Research and Development of Epigenetic Biomarkers”). While FOXO believes these research projects will lead to the discovery, improvement, and commercial validation for the use of its proprietary epigenetic biomarker technology, it cannot guarantee the results of these studies, nor can it guarantee that insurance carriers, agents, underwriters, and consumers will use its products and services based on the results of such studies. FOXO’s results may be misleading or inaccurate, which could adversely impact the acceptance of its products and services, and its overall ability to continue pursuing its business plans. If the results from its research studies differ from what FOXO expects, or if such results are not accepted by insurance carriers, agents, underwriters, and consumers, it will adversely impact FOXO’s ability to pursue its business plans and generate revenue, which could result in a complete loss of your investment.

FOXO intends to provide consumer engagement through its health and wellness platform; however, competition in the personal health and wellness testing market continues to increase and presents a threat to the success of its business.

The number of companies entering the personal health and wellness testing market with offerings similar to those that FOXO intends to provide through its health and wellness testing platform continues to increase. FOXO believes that its ability to offer consumer engagement services that add value to life insurance depends upon many factors both within and beyond its control, including the following:

•        the timing and market acceptance of health and wellness products and services, including the developments and enhancements to those products and services offered by FOXO or its competitors;

•        the customer service and support efforts required to provide personal health and wellness testing services on its platform;

•        the selling and marketing efforts required to support consumers and agents using its consumer engagement services;

•        the ease of use, performance, price and reliability of solutions developed either by FOXO or its competitors; and

•        FOXO’s brand strength relative to its competitors.

FOXO anticipates it will also face competition from other companies attempting to capitalize on the same, or similar, opportunities as it is, including from existing diagnostic, laboratory services and other companies entering the

personal health and wellness testing market with new offerings such as direct access and/or consumer self-pay tests and interpretation services. Some of FOXO’s current and potential competitors have longer operating histories and greater financial, technical, marketing and other resources than it does. These factors may allow FOXO’s competitors to respond more quickly or efficiently than FOXO can to new or emerging technologies. These competitors may engage in more extensive research and development efforts, undertake more far-reaching marketing campaigns and adopt more aggressive pricing policies, which may allow them to build larger customer bases than it has. FOXO’s competitors may develop products or services that are similar to its products and services or that achieve greater market acceptance than its products and services. This could attract customers away from its services and reduce its market share.

FOXO relies on a limited number of critical third-party suppliers for its epigenetic testing services and in the event it is unable to procure their materials or services, it may not be able to find suitable replacements or immediately transition to alternative suppliers, which will have an adverse impact on its business.

FOXO relies on a limited number of critical third-party suppliers for its epigenetic testing, including: (1) the maker of FOXO’s DNA Kit, which is required for the collection of FOXO’s customers’ saliva; (2) a provider of microarray chips; and (3) a provider of array processing and wet-lab services to deliver the raw epigenetics data to FOXO. Its suppliers could cease supplying these materials, equipment and/or services at any time, or fail to provide FOXO with sufficient quantities of materials/services or materials/services that meet its specifications, or significantly increase the costs of providing the materials or services to FOXO. FOXO’s operations could be interrupted if it encounters delays or difficulties in securing these materials or services, or if it cannot locate an acceptable substitute. Any such interruption could significantly impact FOXO’s business, financial condition, results of operations and reputation.

FOXO’s underwriting technology services face substantial competition, which may result in others discovering, developing or commercializing products and services that are similar to FOXO’s, before or more successfully than it can.

While FOXO believes it is the first company to seek to directly apply saliva-based epigenetic biomarker technology to life insurance underwriting, it has not yet developed and commercialized, and may never successfully develop or commercialize, its saliva-based underwriting technology for the insurance market. Moreover, FOXO’s business faces substantial competition from larger, more established companies with products and services that have been accepted by insurance and underwriting markets and may impair FOXO’s ability to compete to commercialize its products and services in the life insurance industry.

FOXO recognizes that other companies, including larger insurance, insurance technology and biotechnology companies, may be developing or have plans to develop products and services that may compete with FOXO’s. Many of FOXO’s competitors have substantially greater financial, technical, and human resources than FOXO has. In addition, many of FOXO’s competitors have significantly greater experience than FOXO has in operating an insurance company, developing various underwriting protocols, and marketing and commercializing products and services similar to FOXO’s. FOXO’s competitors may discover, develop or commercialize products and services that are more effective, safer or less costly than any products or services that FOXO is developing. FOXO’s competitors may also obtain regulatory approval for their products and services more rapidly than FOXO may obtain approval for its planned insurance products, underwriting protocol and testing services.

FOXO anticipates that competition with its insurance products and underwriting testing services will be based on a number of factors, including product efficacy, safety, accuracy, availability and price. FOXO’s competitive position will also depend upon its ability to attract and retain qualified personnel, to obtain patent protection or otherwise develop and maintain proprietary products or processes, protect its intellectual property including its trade secrets, and to secure sufficient capital resources to support the development and commercialization of its products and services.

FOXO or its partners (or both) may now or in the future be subject to laws and regulations relating to laboratory testing, which could materially adversely impact FOXO’s ability to offer its products or services.

The clinical laboratory testing sector is highly regulated in the United States. Both FOXO and its partners may now, or in the future, be subject to regulation under the Clinical Laboratory Improvement Amendments (or CLIA), or similar state laboratory licensure laws. CLIA is a federal law (administered by the Centers for Medicare & Medicaid Services, or CMS) that, in partnership with the states, regulates clinical laboratories that perform testing on specimens derived from humans for the purpose of providing information for the diagnosis, prevention or treatment of disease or impairment of, or assessment of the health of, human beings. CLIA regulations require clinical laboratories to obtain a certificate commensurate with the type of testing being performed and mandate specific standards in areas

including personnel qualifications, administration, participation in proficiency testing, patient test management and quality assurance. CLIA certificates must be renewed every two years, and renewal requires undergoing survey and inspection. CLIA and/or state inspectors may conduct random inspections or conduct inspections as a result of a complaint or reported incident.

DNA methylation profiling of consumer saliva specimens will be performed by FOXO’s wet-laboratory partners. The failure of its laboratory partners to hold CLIA certification or accreditation appropriate to the type of testing they perform, or to comply with CLIA regulations or applicable state licensure requirements could result in adverse regulatory action that, if not timely corrected, could result in FOXO being unable to continue using their services, which could adversely affect FOXO’s business. Similarly, if FOXO’s laboratory partners do not hold state permits or licenses in those states that require them, it may limit FOXO’s ability to offer our products and services on a national basis.

Because FOXO does not directly analyze human specimens in its facilities, but instead performs only data analysis or “dry lab” services, its bioinformatics analysis activities are not subject to CLIA. It is possible that, in the future, CLIA may apply to FOXO’s activities, which could result in FOXO being unable to offer its services or could require additional expenditures to obtain certification, both of which could materially adversely impact its business. FOXO could face similar adverse impacts if a state regulator were to conclude that its bioinformatics activities were subject to state laboratory licensure. Similar adverse consequences could result if CLIA or state regulators disagree with FOXO’s laboratory partners’ interpretation of CLIA or its applicability to their testing services.

FOXO’s underwriting technology and consumer engagement services may now or in the future be subject to laws and regulations relating to laboratory developed tests and software, which could materially adversely impact its business.

The Federal Food, Drug, and Cosmetic Act (or the FDC Act) gives the United States Food and Drug Administration, or FDA, the authority to regulate manufacturers of medical devices, which are defined to include, among other requirements, in vitro diagnostic (or IVD) products (e.g., laboratory instruments, reagents, and collection devices) and software that are intended for use in the diagnosis, treatment, cure, mitigation or prevention of diseases or conditions, including, without limitation, the presence of biomarkers. Medical devices are subject to a variety of regulatory requirements based on their level of risk, including in some cases premarket review and authorization. The FDA enforces its requirements by market surveillance and periodic inspections. The FDA may take a variety of actions in response to violations of the FDC Act and implementing regulations, including, but not limited to, cease and desist orders, injunctions, civil monetary penalties, operating restrictions, or shutdown of production facilities.

The FDA has historically taken the position that laboratory tests developed in-house by a clinical laboratory, sometimes referred to as laboratory developed tests (or LDTs), are subject to regulation as in vitro diagnostic devices. However, the FDA has generally exercised enforcement discretion (i.e., has exercised discretion not to enforce its requirements) with respect to LDTs. Certain types of LDTs have historically not been subject to enforcement discretion, including LDTs for the COVID-19 pandemic and LDTs offered directly to consumers without a health care provider’s order. Legislative proposals introduced in Congress in 2021 seek to codify or, alternatively, eliminate, FDA authority to regulate LDTs.

The FDA also takes the position that stand-alone software that meets the definition of a medical device, known as SaMD, is subject to FDA regulation. Certain categories of medical software, including certain health and wellness software, have been exempted from FDA regulation under the FDC Act. Similarly, the FDA has exercised enforcement discretion with respect to certain types of low risk software products, including those intended to help patients manage chronic conditions.

FOXO’s products and services include epigenetic analysis of laboratory-generated DNA methylation data using its proprietary bioinformatics technology, which it uses to inform both its saliva-based underwriting and molecular health and wellness engagement services. FOXO believes that its products and services are not subject to FDA regulation. First, to the extent its products and services are intended to inform underwriting decisions, they do not meet the definition of a medical device. Second, to the extent FOXO’s products and services incorporate software that is intended solely for health and wellness purposes, it believes such software meets the definition of exempt medical software under the FDC Act, as amended by the 21st Century Cures Act, enacted in 2016. Furthermore, even if elements of FOXO’s products and services could be construed to be subject to FDA oversight, it believes that such elements would be subject to FDA enforcement discretion to the extent that FOXO uses such elements to provide general health and wellness and non-disease-specific information to customers that includes disclaimers and caveats that the information is not intended for medical purposes and poses low risk to consumers.

There can be no guarantee that the FDA will now, or in the future, agree with FOXO’s position. Should the FDA determine that FOXO’s products and services are subject to FDA regulation, FOXO’s operations could be adversely affected. If FDA premarket review or approval were required, FOXO could be forced to stop selling its testing services or be required to modify claims or make other changes while it works to obtain FDA clearance, approval or de novo classification. FOXO’s business, results of operations and financial condition would be negatively affected until such reviews were completed and clearance, approval or de novo classification to market were obtained or the costs of continuing to operate FOXO’s business could increase materially.

FOXO’s use of saliva-based epigenetic biomarkers may in the future be subject to laws and regulations at the state and federal levels relating to the use of such testing or information in life insurance underwriting, which could materially adversely impact FOXO’s business.

Underwriting life insurance is subject to state insurance regulation. We believe the use of epigenetic biomarkers in life insurance underwriting is permissible due to the fact that we are seeking to identify the same underwriting impairments already used by other insurance carriers in medical underwriting today. Moreover, the use of epigenetic testing or information in life insurance underwriting is not prohibited at either the federal or state level. Florida and Louisiana are the only states that have explicitly sought to prohibit the use of genetic information, which is distinguishable from epigenetic information, for use in life insurance underwriting.

Any adverse change in current laws or regulations, or their interpretation, federally or in one or more states in which we operate or plan to operate (or an aggregation of states in which we conduct a significant amount of business) could result in our curtailment or termination of operations in such states, or cause us to not start or modify our operations in a manner that adversely affects our ultimate profitability. Any such action could have a corresponding adverse impact on our results of operations and financial condition, primarily through a material decrease in revenues, and could have a material adverse impact on our business.

FOXO provides ancillary product and service offerings that support its baseline technology, but it cannot guarantee that such products and services will result in material, if any, revenue, and such products and services may be a distraction to FOXO’s main business line initiatives.

FOXO is building a number of technologies to support researchers and epigenetic science and analysis. For example, in 2019 FOXO released “MethylSuite,” a high throughput bioinformatic software package that supports calculating, reporting and interpreting epigenetic data derived from microarray technology. Also in 2019, FOXO participated with the Van Andel Institute and Illumina, Inc. in the commercialization of the Infinium Mouse Methylation Array, a new microarray designed to advance epigenetic research in model organisms. FOXO receives a royalty on all Infinium Mouse Methylation Array sales by Illumina, and also provides laboratory and data processing services to researchers using the Infinium Mouse Methylation Array. However, FOXO does not expect such business lines to result in material, if any, revenues. Furthermore, it cannot guarantee the accuracy or results of the array/data processing or MethylSuite, and any errors in the results provided by such array or bioinformatic software could result in costly litigation, and be a distraction to FOXO’s main business line initiatives.

Risks Related to FOXO’s Life Insurance Operations

FOXO has acquired control of a life insurance company; however, it cannot guarantee that it will satisfy the regulatory conditions in order to transact business.

On August 16, 2021, FOXO received an order (the “AID Order”) from the Commissioner of the Arkansas Insurance Department (the “Commissioner”) approving the acquisition of control of Memorial Insurance Company of America (or “MICOA”), subsequently renamed FOXO Life Insurance Company, which is a life insurance company domiciled in the State of Arkansas. FOXO’s purchase of MICOA primarily involved the purchase of a license to conduct insurance business. In connection with this transaction, the seller (Security National Life Insurance Company (“SNLIC”)) and MICOA entered into the Amended and Restated Reinsurance Agreement whereby the pre-acquisition 100% coinsurance of all of MICOA’s life insurance policies by SNLIC, with all administration also provided by SNLIC, were continued indefinitely after the acquisition of MICOA. The Order from the Arkansas Insurance Department contains the following requirements which must be satisfied in order for FOXO Life Insurance Company to transact business:

•        FOXO Life Insurance Company may not issue new insurance policies without first refiling and receiving the Arkansas Insurance Department’s written approval of its capital maintenance plan and a business plan, including 3-year statutory balance sheet and income statement financial projections with assumptions (“Capital Maintenance Plan” and “Business Plan”);

•        FOXO Life Insurance Company may not seek to expand its authority to do business in any other jurisdiction until the Capital Maintenance Plan and Business Plan has received written approval from the Arkansas Insurance Department;

•        FOXO Life Insurance Company will possess and maintain statutory capital surplus of no less than $5 million until the satisfaction and approval of the Capital Maintenance Plan and Business Plan; and

•        FOXO Life Insurance Company will maintain a risk-based capital of 301% or greater at all times.

FOXO cannot guarantee that the Capital Maintenance Plan and Business Plan will be approved by the Arkansas Insurance Department, or if it will be able to satisfy the Department’s other conditions, including maintaining the required risk-based capital. FOXO has expended and expects to continue to expend substantial time and resources (including significant management focus) in connection with the acquisition of FOXO Life Insurance Company. If the Department does not approve FOXO Life Insurance Company’s Capital Maintenance Plan and Business Plan, it will be unable to sell its life insurance products and generate revenue from the sales of such products or expand its authority to do life insurance business in other jurisdictions, which will have a material adverse impact on its business, financial condition and results of operations.

If FOXO Life Insurance Company fails to meet its statutory capital and/or surplus requirements, it may be subject to adverse regulatory action and its life insurance business will be materially adversely impacted.

The AID Order included the conditions, among others as described above, that FOXO Life Insurance Company must (1) possess and maintain statutory capital and surplus of no less than $5 million, and (2) maintain risk-based capital of three hundred one percent (301%) or greater at all times. Absent the existence of the conditions in the AID Order, Arkansas insurance law presently requires a domestic life insurer to possess and maintain statutory capital of not less than $750,000 and maintain statutory surplus of not less than 15% of its paid-in capital. FOXO Life Insurance Company’s paid-in capital at December 31, 2021 was $1 million.

In addition to minimum statutory capital and statutory surplus laws, domestic Arkansas life insurers are subject to the Risk-Based Capital Act. This law prescribes a formula by which insurers must determine the amount of risk-based capital (“RBC”) they possess. If an insurer’s RBC falls below certain standards, the insurer may be required to take actions of its own choosing to raise its RBC or the Commissioner may be authorized or mandated to require certain actions be taken by the insurer to raise its RBC. The Commissioner also has authority, after a hearing, to find a domestic insurer in “unsound condition” such that further transaction of its business in Arkansas would be hazardous or injurious to policyholders or to the public.

In the event FOXO Life Insurance Company fails to comply with any of the laws described above, and does not take responsive action, which may include receipt of additional capital and/or surplus infusion from FOXO, its Certificate of Authority in Arkansas could be suspended or revoked. Additionally, should FOXO Life Insurance Company’s statutory capital fall below the minimum required by law, it could be placed in court supervised receivership and declared insolvent.

Additionally, as FOXO Life Insurance Company files applications to expand its authority to write business in other states, some of these states may have higher statutory capital and/or surplus requirements than FOXO Life Insurance Company’s domestic state of Arkansas. As a result, FOXO Life Insurance Company may need to increase its statutory capital and/or surplus in order to meet any such requirement of another state in order to obtain its license there. If FOXO Life Insurance Company fails to comply with the above statutory capital and surplus requirements, its life insurance business will be materially adversely impacted.

Obtaining approval from the Arkansas Insurance Department of Delwinds’ acquisition of control of FOXO Life Insurance Company (or an exemption of need for such approval) is a condition to consummating the Business Combination, which approval (or exemption) may not be obtained or obtained in a timely matter, in which case consummation of the Business Combination may be delayed or may not be possible.

Delwinds has filed the Form A with FOXO Life Insurance Company’s domestic state insurance regulator, the Arkansas Insurance Department, requesting the Arkansas Insurance Department’s prior approval of Delwinds’ acquisition of control of FOXO Life Insurance Company as a result of the effectuation of the Business Combination. The Form A contains numerous items of information regarding the applicant, Delwinds, including but not limited to, the method by which it will acquire control of FOXO Life Insurance Company, its corporate structure and ownership structure before and after its acquisition of control of FOXO Life Insurance Company, biographical information regarding its officers

and directors, its audited financial statements and its business plan, inclusive of three-year financial projections. The Arkansas Insurance Department may determine that no Form A filing is required by Delwinds in connection with the Business Combination. However, if no such exemption of the need for the Form A filing is obtained, there can be no assurance that the Arkansas Insurance Department’s review and analysis of the Form A will result in the Arkansas Insurance Department’s approval of Delwinds’ acquisition of control of FOXO Life Insurance Company, or that such approval (or exemption) will be obtained in a timely manner. If the Arkansas Insurance Department’s approval (or exemption) is not obtained, the Business Combination cannot be effectuated.

If FOXO Life Insurance Company is unable to expand its license to transact life insurance into other states, its business could be materially adversely impacted.

In August of 2021, FOXO acquired control of a life insurance company, Memorial Insurance Company of America (subsequently renamed FOXO Life Insurance Company). At the time of acquisition and at present, FOXO Life Insurance Company holds a certificate of authority to conduct the business of life insurance in the State of Arkansas, its state of domicile. Upon the Arkansas Insurance Commissioner’s approval of Delwinds’ Form A, including FOXO Life Insurance Company’s business plan and capital management plan, and consummation of the Combined Business transaction, FOXO expects to file its UCAA applications seeking certificates of authority in other states (“State Expansion Applications”). FOXO’s State Expansion Applications are subject to the approval of each individual state’s insurance regulatory body, and FOXO cannot guarantee that FOXO’s State Expansion Applications will be approved by a specific state or any at all, or that FOXO will be able to meet any additional conditions for approval required by a particular state’s insurance regulatory body. If FOXO State Expansion Applications are not approved, FOXO Life Insurance Company will be unable to sell life insurance products and generate revenue from the sales of such products in jurisdictions where approval is not obtained, which could have a material adverse impact on its business, financial condition and results of operations.

The life insurance industry has experienced an overall decline in product sales which, if this trend continues, could materially adversely impact FOXO’s business and results of operations.

Ownership of life insurance has been in decline in the United States for decades. While FOXO’s products and services are designed to address the overall decline in consumer interest in purchasing life insurance products, there can be no assurance that it will be successful in doing so. The reasons for a decline in household ownership of life insurance are complex and multi-faceted. There can, therefore, be no assurance that FOXO will successfully address these multifaceted reasons or that it will generate revenues or become profitable. FOXO may be forced to make significant changes to its anticipated pricing, sales and revenue models to compete with its competitors’ offerings, and even if such changes are implemented, there is no guarantee that such steps will be successful. If the overall market trend of declining demand for personal life insurance continues or worsens, or FOXO is unable to adjust its approach to meet market demands, its business, financial condition and results of operations could be materially adversely impacted.

Competition in the insurance technology market presents an ongoing challenge to the success of FOXO’s business and if FOXO is unable to compete, its business could be materially adversely impacted.

The number of technology-based companies entering the insurance market with offerings in life insurance continues to increase. While FOXO believes there are very few, if any, companies commercializing saliva-based epigenetic biomarkers or bundling life insurance with a health and wellness engagement platform, FOXO believes that its ability to compete depends upon many factors both within and beyond its control, including the following:

•        the speed and size of FOXO’s customer base it develops;

•        the timing and market acceptance of products and services FOXO offers, including the developments and enhancements to those products and services, offered by FOXO or its competitors;

•        the customer service and support efforts FOXO provides with its products and services;

•        the selling and marketing efforts FOXO employs against its products and services;

•        the acceptance of FOXO’s products by underwriters, insurance companies, agents and consumers;

•        the ease of use, performance, price and reliability of solutions FOXO develops; and

•        the brand strength FOXO creates relative to its competitors.

FOXO will likely face competition from other companies attempting to capitalize on the same, or similar, opportunities as FOXO, including from companies focused on molecular health and wellness, epigenetic biomarkers, and from the overall insurance technology markets inclusive of new offerings such as direct access and/or consumer self-pay tests and genetic interpretation services. Many of FOXO’s current and potential competitors have longer operating histories and greater financial, technical, marketing and other resources than FOXO. These factors may allow FOXO’s competitors to respond more quickly or efficiently than it can to new or emerging technologies. These competitors may engage in more extensive research and development efforts, undertake more far-reaching marketing campaigns, and adopt more aggressive pricing policies, which may allow them to build customer bases larger or faster than FOXO. FOXO’s competitors may develop products or services that are similar to its products and services or that achieve greater market acceptance than its products and services. This could attract customers away from FOXO’s services and reduce its market share or prevent it from increasing.

FOXO may not be successful in establishing the relationships necessary to execute on its business plans, which could have a material adverse impact on its ability to generate revenue and financial condition.

FOXO plans to have its sales and distribution efforts encompass both digital and traditional independent agent distribution channels. Digital distribution channels include direct-to-consumer life insurance sales through its website, as well as digital insurance brokers. Traditional agent distribution channels include independent marketing organizations, broker general agencies and smaller general agencies. In order to serve the broadest range of customers and agents, FOXO intends to establish a managing general agency relationship with a domestic carrier partner, in order for FOXO to expand the use of FOXO’s products and services in connection with a full suite of permanent life insurance products (universal life insurance, variable universal life insurance, indexed universal life insurance, whole life insurance), which it calls its “MGA Model” (see “Information About FOXO — Insurance Products Platform: FOXO Life— MGA Insurance Products”). FOXO envisions the MGA Model will appeal to a domestic carrier partner whose products are widely distributed using traditional independent agent distribution channels and who is seeking a differentiated product offering by combining its own policies with FOXO’s brands and replacing blood and urine specimen for the large portion of its permanent life insurance products that are subject to medical underwriting protocols with FOXO’s saliva-based underwriting protocol.

If FOXO is unable to develop or maintain these relationships, or if its MGA Model proves unworkable, FOXO’s business, financial condition and results of operations may be materially adversely impacted. Moreover, while FOXO will strive to demonstrate the value of its products and services to consumers, insurance agents, and carriers, these potential customers may not embrace its products and services, thereby hindering FOXO’s ability to execute on its business plans and generate revenue.

Denial of claims or FOXO’s failure to accurately and timely pay claims could materially and adversely impact its business, financial condition, and results of operations.

FOXO Life Insurance Company must accurately and timely evaluate and pay claims that are made by its customers under its proprietary insurance policies. Many factors affect FOXO’s ability to pay claims accurately and timely, including the efficacy of its claims processing, the training and experience of its claims adjusters and its ability to develop or select and implement appropriate procedures and systems to support its claims functions.

If FOXO Life Insurance Company’s claims adjusters are unable to effectively process its claims, FOXO’s ability to grow its business while maintaining high levels of customer satisfaction could be compromised and FOXO could lose valuable customers or damage customer relationships, suffer negative publicity, and lose revenues.

If FOXO is unable to underwrite risks accurately and charge competitive yet profitable premium rates to its future customers, its business, results of operations and financial condition will be adversely impacted.

In general, the premium rates for insurance are established at the time a policy is issued and, therefore, before all of FOXO’s underlying costs are known, including the rates acceptable to applicable reinsurance companies. The accuracy of FOXO’s premium rate pricing will be subject to its ability to adequately assess risks, estimate losses and comply with state insurance regulations. Like other life insurance companies, FOXO Life Insurance Company will consider age, gender, health and mortality and other assumptions in setting its premium rates. FOXO Life Insurance Company also utilizes the data that it gathers through its interactions with its customers, as evaluated, and potentially curated by its proprietary artificial intelligence algorithms. In addition, FOXO Life Insurance Company expects that its rates will be based on its epigenetic biomarkers, which may prove to be inaccurate.

Establishing adequate premium rates is necessary, together with investment income, if any, to generate sufficient revenue to offset losses, loss adjustment expenses, marketing expenses, and other costs. If FOXO Life Insurance Company does not accurately assess the risks that it underwrites, it may not charge adequate premiums to cover its losses and expenses, which would adversely affect its results of operations and its profitability. Alternatively, FOXO Life Insurance Company could set its premiums too high, which could reduce its competitiveness and lead to lower revenues, which could have a material adverse effect on its business, financial condition and results of operations.

Pricing involves the acquisition and analysis of historical loss data and the projection of future trends, loss costs and expenses, and inflation trends, among other factors, for each of FOXO Life Insurance Company’s products in multiple risk tiers and many different markets. In order to accurately price its policies, FOXO Life Insurance Company must:

•        collect and properly analyze a substantial volume of data from its customers;

•        develop, test and apply appropriate actuarial projections and rating formulas;

•        review and evaluate competitive product offerings and pricing dynamics; and

•        closely monitor and timely recognize changes in trends.

There are no assurances that FOXO Life Insurance Company will have success in implementing its planned pricing methodology accurately in accordance with its assumptions. FOXO Life Insurance Company’s ability to accurately price its policies is subject to a number of risks and uncertainties, including:

•        insufficient or unreliable data;

•        incorrect or incomplete analysis of available data;

•        incorrect mortality data;

•        uncertainties generally inherent in estimates and assumptions;

•        FOXO Life Insurance Company’s failure to implement appropriate actuarial projections and rating formulas or other pricing methodologies;

•        incorrect or incomplete analysis of the competitive environment; and

•        FOXO Life Insurance Company’s failure to accurately estimate investment yields loss and loss adjustment expense(s), as well as unanticipated court decisions, legislation or regulatory action.

To address the potential inadequacy of FOXO’s business model, FOXO may in the future be compelled to increase the amount of reserves allocated to cover policy claims, increase premium rates or adopt tighter underwriting standards, any of which may result in a decline in new business and, as a result, could have a material adverse impact on its business, financial condition and results of operations.

Unexpected changes in the interpretation of FOXO Life Insurance Company’s coverage or provisions, including loss limitations and exclusions in its policies could have a material adverse impact on its financial condition and results of operations.

There can be no assurance that specifically negotiated loss limitations or exclusions in FOXO Life Insurance Company’s planned life insurance policies will be enforceable in the manner it intends. As industry practices and legal, judicial, social, and other conditions change, unexpected and unintended issues related to claims and coverage may emerge. While loss limitations and exclusions help FOXO Life Insurance Company assess and mitigate its loss exposure, it is possible that a court or regulatory authority could nullify or void a limitation or exclusion, or legislation could be enacted modifying or barring the use of such limitations or exclusions. These types of governmental actions could result in higher than anticipated losses, which could have a material adverse impact on FOXO Life Insurance Company’s financial condition or results of operations. In addition, court decisions could read policy exclusions narrowly so as to expand coverage, thereby requiring insurers to create and write new exclusions. These issues may adversely affect FOXO Life Insurance Company’s business by either broadening coverage beyond its underwriting intent or by increasing the severity of claims. In some instances, these changes may not become apparent until sometime after FOXO Life Insurance Company has issued insurance contracts that are affected by the changes. As a result, the full extent of liability under any of its insurance contracts may not be known for many years after a contract is issued.

FOXO intends to obtain reinsurance from a third-party reinsurance carrier in connection with its life insurance products issued by FOXO Life Insurance Company. FOXO may not be successful in obtaining reinsurance, or reinsurance may only be available at certain prices, which may limit FOXO Life Insurance Company’s ability to write new business. Furthermore, reinsurance subjects FOXO Life Insurance Company to counterparty risk and may not be adequate to protect it against losses, which could have a material impact on its results of operations and financial condition.

Reinsurance is a contract by which an insurer, generally referred to as the ceding insurer, agrees with a second insurer, called a reinsurer, that the reinsurer will cover a portion of the losses incurred by the ceding insurer in the event a claim is made under a policy issued by the ceding insurer, in exchange for a premium. If FOXO is not able to purchase reinsurance in sufficient amounts or for adequate prices, there will be unexpected performance which could adversely affect financial results. Although FOXO believes its planned reinsurance counterparties will be liable to it according to the terms of the reinsurance policies, it will remain primarily liable to its policyholders as the direct insurer on all risks reinsured. As a result, reinsurance does not eliminate FOXO Life Insurance Company’s obligation to pay all claims, and FOXO is subject to the risk that one or more of its planned reinsurers will be unable or unwilling to honor its obligations, that the reinsurers will not pay in a timely fashion, or that FOXO Life Insurance Company’s losses will be so large that they exceed the limits inherent in its reinsurance contracts, limiting recovery. Reinsurers may become financially unsound by the time that they are called upon to pay amounts due, which may not occur for many years, in which case FOXO Life Insurance Company may have no legal ability to recover what is due to it under its agreement with such reinsurer. Any disputes with reinsurers regarding coverage under reinsurance contracts could be time consuming, costly, and uncertain of success.

The unavailability of acceptable reinsurance would have an adverse impact on FOXO’s business model, which depends on reinsurance companies to absorb any unfavorable variance from the level of losses anticipated at underwriting. If FOXO is unable to obtain or maintain adequate reinsurance at reasonable rates, it would have to increase its risk exposure or reduce the level of its underwriting commitments, each of which could have a material adverse effect on its business volume and profitability. Alternatively, FOXO could elect to pay higher than reasonable rates for reinsurance coverage, which could have a material adverse effect upon its profitability.

In addition, selling FOXO’s epigenetic underwriting protocol relies on reinsurance carriers accepting the risk related to its use, and if reinsurance carriers do not accept such risk, FOXO may not be able to affect its business plan for its underwriting services model, which could negatively impact its results of operations and its financial condition.

FOXO Life Insurance Company’s reinsurer, Security National Life Insurance Company (or SNLIC), may not fulfill its contractual obligation and take action necessary to preserve FOXO Life Insurance Company’s ability to take reserves credit for the policy liabilities ceded to SNLIC, which would have a detrimental effect on FOXO LIFE’s statutory balance sheets and could threaten its solvency.

As of the date of the closing of FOXO’s purchase of Memorial Insurance Company of America (or MICOA), subsequently renamed FOXO Life Insurance Company, an amended and restated indemnity reinsurance agreement went into effect between FOXO Life Insurance Company and its parent company at the time of the closing, Security National Life Insurance Company, a Utah domiciled insurer, or SNLIC. Under the terms of that reinsurance agreement, MICOA ceded, and SNLIC, assumed, any and all present and future liabilities of MICOA under certain life insurance policies and any other policies that may have been on MICOA’s books as of the date of the closing, for the lifetime of all such policies. SNLIC also assumed full responsibility for administering the reinsured policies for as long as any of them remain in force. Under current insurance laws, MICOA (now FOXO Life Insurance Company) can take statutory financial credit for the reserves it ceded to SNLIC in connection with the policy liabilities assumed by SNLIC, because SNLIC is licensed as a foreign admitted insurer in Arkansas, FOXO Life Insurance Company’s domestic state. However, if for any reason SNLIC should cease to be a licensed, admitted insurer in Arkansas, FOXO Life Insurance Company would no longer be permitted to take credit for the statutory reserves ceded to SNLIC on its statutory financial statements unless SNLIC established a trust account into which the reserves funds were deposited subject to withdrawal by FOXO Life Insurance Company, or SNLIC took some other form of action to enable FOXO Life Insurance Company to continue to receive full reserves credit on its statutory financial statements. Under the terms of the amended and restated reinsurance agreement, SNLIC is obligated to take any action necessary to permit FOXO Life Insurance Company to be able to continue to, at all times, be able to take reserves credit for the ceded policies on its statutory financial statements. Nevertheless, it cannot be stated with certainty that SNLIC would fulfill its contractual obligation and take any actions necessary to preserve FOXO Life Insurance Company’s ability to take reserves credit for the policy liabilities ceded to SNLIC. If SNLIC did not take such actions, it is likely that FOXO Life Insurance Company would no longer be permitted to take credit for the reserves on its statutory financial statements. This would have a detrimental effect on FOXO Life Insurance Company’s statutory balance sheet and could threaten its solvency.

The business of FOXO Life Insurance Company may depend on search engines, social media platforms, content-based online advertising and other online sources to attract consumers to its website, which may be affected by third-party interference beyond its control, and as it grows, its customer acquisition costs will continue to rise.

The success of FOXO Life Insurance Company depends on its ability to attract consumers to its websites and convert them into customers in a cost-effective manner. FOXO Life Insurance Company may depend, in large part, on search engines, social media platforms, content-based online advertising and other online sources for traffic to its website.

With respect to search engines, FOXO Life Insurance Company plans to be included in search results as a result of both paid search listings, where it purchases specific search terms that result in the inclusion of its advertisement, and free search listings, which depend on algorithms used by search engines. For paid search listings, if one or more of the search engines or other online sources on which FOXO Life Insurance Company relies for purchased listings modifies or terminates its relationship with FOXO Life Insurance Company, its expenses could rise, it could lose consumers and traffic to its website could decrease, any of which could have a material adverse impact on its business, results of operations and financial condition. For free search listings, if search engines on which FOXO Life Insurance Company relies for algorithmic listings modify their algorithms, its website may appear less prominently or not at all in search results, which could result in reduced traffic to its website.

FOXO’s ability to maintain and increase the number of future consumers directed to its products from digital platforms is not within its control. Search engines, social media platforms and other online sources often revise their algorithms and introduce new advertising products. If one or more of the search engines or other online sources on which FOXO relies for traffic to its website were to modify its general methodology for how it displays its advertisements or keyword search results, resulting in fewer consumers clicking through to its websites, the business and operating results of FOXO Life Insurance Company are likely to suffer. In addition, if FOXO online display advertisements are no longer effective or are not able to reach certain consumers due to consumers’ use of ad-blocking software, the business and operating results of FOXO Life Insurance Company could suffer.

Additionally, changes in regulations could limit the ability of search engines and social media platforms, including, but not limited to, Google and Meta, to collect data from users and engage in targeted advertising, making them less effective in disseminating FOXO’s advertisements to its target customers. For example, the proposed Designing Accounting Safeguards to Help Broaden Oversight and Regulations on Data Act would mandate annual disclosure to the SEC of the type and “aggregate value” of user data used by harvesting companies, such as, but not limited to, Google, Meta and Amazon, including how revenue is generated by user data and what measures are taken to protect the data. If the costs of advertising on search engines and social media platforms increase, FOXO may incur additional marketing expenses or be required to allocate a larger portion of its marketing spend to other channels and the business and operating results of FOXO Life Insurance Company could be adversely impacted. Similarly, insurance brokerage and distribution regulation may limit its ability to rely on key distribution platforms if the third-party distribution platforms are unable to continue to distribute its insurance products pursuant to insurance law and regulations.

FOXO also plans to attract customers through its relationships with certain business development partners. If its business development partners were to charge higher rates or decide to terminate their relationships with FOXO, its ability to attract customers could be materially adversely impacted. FOXO’s efforts to acquire customers through direct marketing may subject it to increased regulatory scrutiny by state insurance regulators pursuant to unfair methods of competition or unfair or deceptive acts or practices laws.

Interruptions or delays in the services provided by FOXO’s internet service providers could adversely impact the operability of the planned website for FOXO Life Insurance Company and may cause FOXO’s business to suffer.

FOXO plans to offer FOXO Life Insurance Company products through its website. FOXO will need to rely on the internet and, accordingly, depend on the continuous, reliable and secure operation of internet servers, related hardware and software, and network infrastructure. The operations of FOXO will depend on protecting the virtual cloud infrastructure by maintaining its configuration, architecture, and interconnection specifications. Although FOXO plans to have disaster recovery plans, it may still be vulnerable to damage or interruption from human error, intentional bad acts, earthquakes, floods, fires, severe storms, war, terrorist attacks, power losses, hardware failures, systems failures, telecommunications failures, and similar events, many of which are beyond its control, any of which could disrupt its services, prevent customers from accessing its products, destroy customer data, or prevent FOXO

from being able to continuously back up and record data. FOXO may also incur significant costs for using alternative equipment or taking other actions in preparation for, or in reaction to, events that damage the services it plans to use. Although FOXO plans to carry business interruption insurance, it may be insufficient to compensate it for the potentially significant losses, including the potential harm to the future growth of its business that may result from interruptions in the availability of the services or products of FOXO Life Insurance Company.

As FOXO begins to obtain and expand the number of customers to whom it plans to provide FOXO Life Insurance Company products and services, it may not be able to scale its technology to accommodate the increased capacity requirements, which may result in interruptions or delays in service, which could have a materially adverse impact on its business, financial condition and results of operations.

FOXO, as part of its insurance business, will collect, process, store, share, disclose and use customer information and other data, and its actual or perceived failure to protect such information and data, respect customer privacy or comply with data privacy and security laws and regulations could damage its reputation and brand and harm its business and operating results.

FOXO receives and stores a large volume of personally identifiable information, epigenetic information, and other data relating to its customers, as well as other personally identifiable information and other data relating to individuals such as its employees. Security breaches, employee malfeasance, or human or technological error could lead to potential unauthorized disclosure of its customers’ personal information. Even the perception that the privacy of personal information is not satisfactorily protected or does not meet regulatory requirements could inhibit sales of FOXO’s solutions and any failure to comply with such laws and regulations could lead to significant fines, penalties or other liabilities.

A security compromise of FOXO’s information systems or of those of businesses with whom it interacts that results in confidential information being accessed by unauthorized or improper persons could harm FOXO’s reputation and expose it to regulatory actions, customer attrition, remediation expenses, disruption of its business, and claims brought by its customers or others for breaching contractual confidentiality and security provisions or data protection laws. Monetary damages imposed on FOXO could be significant and not covered by its liability insurance. Techniques used by bad actors to obtain unauthorized access, disable or degrade service, or sabotage systems evolve frequently and may not immediately produce signs of intrusion, and FOXO may be unable to anticipate these techniques or to implement adequate preventative measures. In addition, a security breach could require FOXO to expend substantial additional resources related to the security of its information systems and provide required breach notifications and remediation, diverting resources from other projects and disrupting its businesses. If FOXO experiences a data security breach, its reputation could be damaged and it could be subject to additional litigation, regulatory risks and business losses.

Numerous local, municipal, state, federal, and international laws and regulations address privacy and the collection, storing, sharing, use, disclosure, and protection of certain types of data, including the Personal Information Protection and Electronic Documents Act, the Telephone Consumer Protection Act of 1991, or the TCPA, Section 5 of the Federal Trade Commission Act, and effective as of January 1, 2020, the California Consumer Privacy Act (or the CCPA). These laws, rules, and regulations evolve frequently and their scope may continually change, through new legislation, amendments to existing legislation, and changes in enforcement, and may be inconsistent from one jurisdiction to another. For example, the CCPA, which went into effect on January 1, 2020, requires, among other things, new disclosures to California consumers and affords such consumers new abilities to opt out of certain sales of personal information. The CCPA provides for fines of up to $7,500 per violation. Aspects of the CCPA and its interpretation and enforcement remain uncertain. The effects of this legislation are potentially far-reaching and may require FOXO to modify its data processing practices and policies and incur substantial compliance-related costs and expenses. The CCPA has been amended on multiple occasions. For example, the California Privacy Rights Act (or CPRA) recently was approved by California voters and significantly modifies the CCPA, potentially resulting in further uncertainty and requiring FOXO to incur additional costs and expenses in an effort to comply. The CPRA does not become operative until January 1, 2023 (and then applies only to consumer data collected on or after January 1, 2022, with enforcement beginning July 1, 2023). While the CCPA will remain operative and enforceable from now until July 1, 2023, FOXO will continue to monitor developments related to the CPRA. The effects of this legislation are potentially far-reaching and may require FOXO to modify its data processing practices and policies and incur substantial compliance-related costs and expenses. Additionally, many laws and regulations relating to privacy and the collection, storing, sharing, use, disclosure, and protection of certain types of data are subject to varying degrees of enforcement and new and changing interpretations by courts. The CCPA and other changes in laws or regulations relating to privacy, data protection, breach notifications, and information security, particularly any new or modified laws or regulations, or changes to the interpretation or enforcement of such laws or regulations, which require enhanced protection

of certain types of data or new obligations with regard to data retention, transfer, or disclosure, could greatly increase the cost of providing FOXO’s platform, require significant changes to its operations, or even prevent it from providing its platform in jurisdictions in which it currently operates and in which it may operate in the future.

FOXO may also be required to comply with increasingly complex and changing data security and privacy regulations in the UK, the European Union (or the EU) and in other jurisdictions in which FOXO plans to conduct business that regulate the collection, use and transfer of personal data, including the transfer of personal data between or among countries. For example, the EU’s General Data Protection Regulation (or the GDPR), now also enacted in the UK as the UK GDPR, has imposed stringent compliance obligations regarding the handling of personal data and has resulted in the issuance of significant financial penalties for noncompliance. Further, in July 2020, the Court of Justice of the European Union released a decision in the Schrems II case (Data Protection Commission v. Facebook Ireland, Schrems), declaring the EU-US Privacy Shield invalid and calling into question data transfers carried out under the European Commission’s Standard Contractual Clauses. As a result of the decision, FOXO may face additional scrutiny from EU regulators in relation to the transfer of personal data from the EU to the United States. Noncompliance with the GDPR can trigger fines of up to the greater of €20 million or 4% of global annual revenues. In the United States, there have been proposals for federal privacy legislation and many new state privacy laws proposed. Other countries have enacted or are considering enacting data localization laws that require certain data to stay within their borders. FOXO may also face audits or investigations by one or more domestic or foreign government agencies or its customers pursuant to its contractual obligations relating to its compliance with these regulations. Complying with changing regulatory requirements requires FOXO to incur substantial costs, exposes it to potential regulatory action or litigation, and may require changes to its business practices in certain jurisdictions, any of which could materially adversely impact its business, financial condition and results of operations.

Despite FOXO’s efforts to comply with applicable laws, regulations, and other obligations relating to privacy, data protection, and information security, it is possible that its interpretations of the law, best practices, or platform implementation could be inconsistent with, or fail, or be alleged to fail to meet all requirements of, such laws, regulations, or obligations. FOXO’s failure, or the failure by its third-party providers on its platform, to comply with applicable laws or regulations or any other obligations relating to privacy, data protection, or information security, or any compromise of security that results in unauthorized access to, or use or release of personally identifiable information or other data relating to FOXO’s customers, or other individuals, or the perception that any of the foregoing types of failure or compromise have occurred, could damage FOXO’s reputation, discourage new and existing customers from using its platform, or result in fines, investigations, or proceedings by governmental agencies and private claims and litigation, any of which could adversely affect its business, financial condition, and results of operations. Even if not subject to legal challenge, the perception of privacy concerns, whether or not valid, may harm FOXO’s reputation and brand and materially adversely impact its business, financial condition, and results of operations.

FOXO will be subject to the terms of its privacy policies and privacy-related obligations. Any failure or perceived failure by FOXO to comply with its privacy policies, its privacy-related obligations to customers or others, or its privacy-related legal obligations, or any compromise of security that results in the unauthorized release or transfer of sensitive information, which could include personally identifiable information or other user data, may result in governmental or regulatory investigations, enforcement actions, regulatory fines, compliance orders, litigation or public statements against FOXO by consumer advocacy groups or others, and could cause customers to lose trust in FOXO, all of which could be costly and have an adverse impact on its business. In addition, new and changed rules and regulations regarding privacy, data protection (in particular those that impact the use of artificial intelligence) and cross-border transfers of customer information could cause FOXO to delay planned uses and disclosures of data to comply with applicable privacy and data protection requirements. Moreover, if any third-party that FOXO works with violates applicable laws or its policies, such violations also may put personal information at risk, which may result in increased regulatory scrutiny and have a material adverse effect on its reputation, business, financial condition and results of operations.

FOXO may be unable to prevent or address the misappropriation of its data, which could damage FOXO’s reputation and materially adversely impact its business.

Third parties may misappropriate FOXO’s data through website scraping, bots or other means and aggregate this data on their websites with data from other companies. In addition, copycat websites or online apps may misappropriate data and attempt to imitate FOXO’s brand or the functionality of its planned website. If FOXO becomes aware of such websites or online apps, FOXO intends to employ technological or legal measures in an attempt to halt their operations. However, FOXO may be unable to detect all such websites or online apps in a timely manner and, even if it could, technological and legal measures may be insufficient to halt their operations immediately or completely.

In some cases, particularly in the case of websites or online apps operating outside of the United States, FOXO’s available remedies may not be adequate to protect it against the effect of the operation of such websites or online apps. Regardless of whether FOXO can successfully enforce its rights against the operators of these websites or online apps, any measures that FOXO may take could require it to expend significant financial or other resources, which could harm its business, results of operations or financial condition. In addition, to the extent that such activity creates confusion among consumers or advertisers, FOXO’s brand and business could be harmed.

Risks Related to Regulation Applicable to FOXO Life Insurance Company

FOXO Life Insurance Company will be subject to extensive insurance industry regulations in each state in which it operates.

In the United States, each state regulator retains the authority to license insurers in its respective state, and an insurer generally may not operate in a state in which it is not licensed. Accordingly, FOXO Life Insurance Company is not currently, and may not be permitted to sell insurance to residents of certain states and territories of the United States, which is likely to put FOXO at a disadvantage among many of its competitors that have been in business much longer than it and are licensed to sell their insurance products in most, if not all, U.S. jurisdictions.

FOXO will be subject to extensive regulation and supervision in the states in which it transacts business by the individual state insurance departments. This regulation is generally designed to protect the interests of customers, and not necessarily the interests of insurers or agents, their stockholders or other investors. Numerous aspects of FOXO’s insurance business are subject to regulation, including, but not limited to, risk classification factors, mandatory covered risks, prohibited exclusions, licensing and appointment of agents, restrictions on the size of risks that may be insured under a single policy, reserves and provisions for unearned premiums, losses and other obligations, deposits of securities for the benefit of customers, investments and capital, policy forms and coverages, advertising and other conduct, including restrictions on the use of credit information and other factors in underwriting, as well as other underwriting and claims practices. To the extent FOXO decides to expand its current product to include other insurance products, this would subject FOXO to additional regulatory requirements and scrutiny in each state in which FOXO elects to offer such products. States have also adopted legislation defining and prohibiting unfair methods of competition and unfair or deceptive acts and practices in the business of insurance. Prohibited practices include, but are not limited to, rebating, misrepresentations, false advertising, coercion, disparaging other insurers, unfair claims settlement procedures, and discrimination in the business of insurance. Noncompliance with any of such state statutes may subject FOXO to regulatory action by the relevant state insurance regulator, and, in certain states, private litigation. States also regulate various aspects of the contractual relationships between insurers and independent agents.

Such laws, rules and regulations are usually overseen and enforced by the various state insurance departments, as well as through private rights of action and by state attorneys general. Such regulations or enforcement actions are often responsive to current consumer and political sensitivities, including those which may arise after a major event. Such rules and regulations may result in rate suppression, limit FOXO’s ability to manage its exposure to unprofitable or volatile risks, or lead to fines, premium refunds or other adverse consequences. The federal government also may regulate aspects of FOXO’s businesses, such as the protection of consumer genetic or epigenetic information or the use of consumer insurance (or credit) scores to underwrite and assess the risk of customers. Among other things, the Fair Credit Reporting Act (or FCRA) requires insurance companies to have a permissible purpose before obtaining and using a consumer report for underwriting purposes, as well as comply with related notice and recordkeeping requirements. The Genetic Information Nondiscrimination Act (or GINA) prohibits health plans and issuers from requesting or requiring an individual to undergo a genetic test. Although GINA currently only applies to the use of genetic information in health insurance, its prohibitions could be expanded to include life insurance and/or epigenetics. Failure to comply with federal requirements under the FCRA, GINA, or any other applicable federal laws would subject FOXO to regulatory fines and other sanctions. In addition, given FOXO’s short operating history, there may be a greater likelihood of regulators identifying errors in FOXO’s life insurance operations, such as in the newly introduced policy forms it uses, its methods of customer communications, or its claims practices. As a result of such noncompliance, regulators could impose fines or other penalties, including cease-and-desist orders for an individual state, or all states, until the identified noncompliance is rectified.

FOXO’s ability to obtain state licenses depends on its ability to meet licensing requirements in each state, usually and largely established by The National Association of Insurance Commissioners (or NAIC) and adopted by each state, subject to variations across states. If after obtaining licensure FOXO is unable to satisfy the applicable licensing requirements of any particular state, it could lose its license to do business in such state, which would result in the temporary or permanent

cessation of its operations in that state. Alternatively, if FOXO is unable to satisfy applicable state licensing requirements, it may be subject to additional regulatory oversight, have its license suspended, or be subject to seizure of assets. Any such events could materially adversely impact its business, financial condition and results of operations.

Further, federal, state and/or local government actions to address the impact of the COVID-19 pandemic may adversely impact FOXO. Regulatory restrictions or requirements have impacted or may impact pricing, risk selection and FOXO’s rights and obligations with respect to its policies and customers, including its ability to cancel policies and/or demand premium payment according to policy terms. Several state regulators have issued orders, and may issue additional orders, requiring insurers to offer deferred payment options, and regulators in other states could take similar actions or renew such actions that have expired. Many insurers have voluntarily provided, and may further provide, deferred payment options to customers. It is also possible that changes in economic conditions and steps taken by federal, state and local governments in response to the COVID-19 pandemic could require an increase in taxes at the federal, state and local levels, which would adversely impact FOXO’s results of operations.

Changes in state laws and regulations governing FOXO’s business, or changes in the interpretation of such laws and regulations, could negatively impact its business.

State statutes typically provide state regulatory agencies with significant powers to interpret, administer and enforce the laws relating to the purchase of life insurance policies. Under statutory authority, state regulators have broad discretionary power and may impose new licensing requirements, interpret or enforce existing regulatory requirements in different ways or issue new administrative rules, even if not contained in state statutes. State regulators may also impose rules that may restrict and negatively impact FOXO’s industry. Because of the history of certain abuses in the industry, FOXO believes it is likely that state insurance regulation will increase and grow more complex during the foreseeable future. FOXO cannot, however, predict what any new regulation would specifically involve.

The emergence of new biotechnologies has led to frequent legislation governing the use of genetic information in insurance. The federal regulation, GINA, prohibits the use of genetic information by health insurers, but it does not apply to life insurance or epigenetics at this time. To date, a small minority of states have adopted a GINA-like framework, essentially prohibiting the use of genetic information for life insurance underwriting and risk classification. Other states have laws regulating, though not prohibiting, the use of genetic information in life insurance. While epigenetics’ distinguishable features exempt it from the text of, and rationale behind, current laws regulating the use of genetic information in life insurance, any adverse change in present laws or regulations, or their interpretation in one or more states in which FOXO may operate (or an aggregation of states in which FOXO may conduct a significant amount of business) could result in FOXO’s curtailment or termination of operations in such jurisdictions, or cause it to modify its operations in a way that adversely affects its profitability. Any such action could have a corresponding material and negative impact on FOXO’s results of operations and financial condition, primarily through a material decrease in revenues, and could also have a material adverse effect on its business, financial condition and results of operations.

Failure to maintain FOXO Life Insurance Company’s risk-based capital at the required levels could adversely impact its ability to maintain regulatory authority to conduct its business.

FOXO Life Insurance Company must have sufficient capital to comply with insurance regulatory requirements and maintain authority to conduct its business. State regulators enforce a system that includes the implementation of standards developed by the NAIC to test the adequacy of statutory capital of U.S.-based insurers. This system establishes the minimum amount of capital necessary for an insurance company to support its overall business operations. It identifies insurers that may be inadequately capitalized by looking at certain inherent risks of each insurer’s assets and liabilities and its mix of net written premiums. Insurers falling below a calculated threshold may be subject to varying degrees of regulatory action, including supervision, rehabilitation or liquidation. Moreover, as a new entrant to the insurance industry, FOXO Life Insurance Company may face additional capital requirements from its domestic regulator or other state insurance departments as compared to those of its larger and more established competitors. Failure to maintain adequate risk-based capital at the required levels could adversely impact FOXO Life Insurance Company’s ability to conduct its business.

New legislation or legal requirements may affect how FOXO communicates with its customers, which could have a material adverse impact on its business model, financial condition, and results of operations.

State and federal lawmakers and insurance regulators are focusing upon the use of customer communications, including concerns about transparency, deception, and fairness, in particular. Changes in laws or regulations, or changes in the interpretation of laws or regulations by a regulatory authority may decrease FOXO’s revenues and earnings and

may require FOXO to change the manner in which it conducts some aspects of its business. In addition, FOXO’s business and operations are subject to various U.S. federal, state, and local consumer protection laws, including laws which place restrictions on the use of automated tools and technologies to communicate with wireless telephone subscribers or consumers generally. For example, a California law, effective as of July 2019, makes it unlawful for any person to use a bot to communicate with a person in California online with the intent to mislead the other person about its artificial identity for the purpose of knowingly deceiving the person about the content of the communication in order to incentivize a purchase of goods or services in a commercial transaction. Although FOXO takes steps to comply with this and other laws restricting the use of electronic communication tools, no assurance can be given that FOXO will not be exposed to civil litigation or regulatory enforcement. Further, to the extent that any changes in law or regulation further restrict the ways in which FOXO communicate with prospective or current customers before or during onboarding, customer care, or claims management, or otherwise, these restrictions could result in a material reduction in its customer acquisition and retention, reducing the growth prospects of its business, and materially adversely impact its business, financial condition and results of operations.

FOXO Life Insurance Company will be periodically subject to examinations by its primary state insurance regulator, which could result in adverse examination findings and necessitate remedial actions. In addition, insurance regulators of other states in which FOXO Life Insurance Company intends to seek licenses to operate may also conduct examinations or other targeted investigations, which may also result in adverse examination findings and necessitate remedial actions.

Periodically, state regulatory agencies may perform examinations of insurance companies under each respective jurisdiction to assess compliance with applicable laws and regulations, financial condition and the conduct of regulated activities. These periodic examinations provide regulatory agencies a significant opportunity to review and scrutinize FOXO’s business. Typically, financial examinations are carried out by the insurer’s domestic regulator under a system of domestic deference adopted by each state. Market conduct examinations can be and are done by any state where an insurer is licensed (sometimes in the form of multi-state examinations). If, as a result of any examination, a state regulatory agency determines that FOXO’s financial condition, capital resources, or other aspects of any of its planned insurance operations are less than satisfactory, or that FOXO is in violation of applicable laws or regulations, they may require FOXO to take one or more remedial actions or otherwise subject FOXO to regulatory scrutiny, such as pursuant to an enforcement action. FOXO cannot predict with precision the likelihood, nature, or extent of any necessary remedial actions, if any, resulting from any examination, or the associated costs of such remedial actions or regulatory scrutiny. Any regulatory or enforcement action or any regulatory order imposing remedial, injunctive, or other corrective action against FOXO resulting from these examinations or investigations could have a material adverse impact on FOXO’s reputation, business, financial condition and results of operations.

Risks Related to FOXO’s Intellectual Property

If FOXO is unable to retain its license for patent pending methods of identifying epigenetic biomarkers, its business plans, revenue generation, and ability to continue operating could be adversely impacted.

FOXO, through its subsidiary FOXO Labs, has an exclusive license for U.S. patent applications directed to three epigenetic clocks for use in life insurance, which are known as Mortality Predictor EEAA, PhenoAge and GrimAge. Subject matter that was directed solely to abstract ideas or natural laws, such as the discovery and determination of correlations, has been found to lack patent eligibility by the USPTO, if found to lack “something more.” If one or more of these three patent-pending methods of determining epigenetic estimations of age and/or age acceleration by use of a particular combination of epigenetic biomarkers of health and wellness and biological aging do not receive full patent approval, or if FOXO is unable to retain its exclusive license, it may not be able exclusively to apply such methods to its planned life insurance underwriting protocol, which may put FOXO at a competitive disadvantage, which could adversely impact its ability to operate its business as intended and achieve its business objectives.

If FOXO is unable to protect its patent pending methods of identifying saliva-based epigenetic biomarkers or intellectual property in general, the value of its brand and other intangible assets may be diminished, and its business may be adversely impacted.

FOXO depends on its proprietary technology, intellectual property and services for its business plans, success and ability to compete. FOXO relies and expects to continue to rely on a combination of confidentiality and other agreements with its employees, consultants and third parties with whom it has relationships or with whom it plans to have relationships,

and who may have access to confidential or patentable aspects of its research and development output, as well as the trademark, copyright, patent and trade secret protection and common law rights and laws, to protect its proprietary rights. For example, FOXO relies on trade secret protection for building and validating an extensive number of machine learning models that use epigenetic data derived from different types of tissues to predict a wide variety of targets, such as direct mappings to life insurance classification, smoking use and/or extent, alcohol use and/or extent, etc. Although FOXO enters into confidentiality and other agreements to protect these and other proprietary technologies, any of these parties may breach the agreements and disclose information before a patent application is filed, and jeopardize FOXO’s ability to seek patent protection, if it were not able to use the courts to enjoin the disclosure in advance. In addition, FOXO’s ability to obtain and maintain valid and enforceable patents or patent licenses depends on whether the differences between its inventions and the prior art allow its inventions to be patentable over the prior art. Since publications in the scientific literature often lag behind the actual discoveries, and patent applications do not publish until 18 months after filing, FOXO is never certain that it is the first to make the inventions claimed in any of its patents or that it is the first to file for patent protection of such patents. In other words, priority is never known until an application is prosecuted. Additionally, third parties may knowingly or unknowingly infringe FOXO’s proprietary rights, and third parties may challenge its proprietary rights held, pending and future patent, copyright, trademark and other applications, which, if successful, may not be approved and which may affect FOXO’s ability to prevent infringement without incurring substantial expense. In addition, the laws of some foreign countries do not protect proprietary rights to the same extent as do the laws of the United States.

If the protection of FOXO’s proprietary rights is inadequate to prevent use or appropriation by third parties, the value of its brand and other intangible assets may be diminished and competitors may be able to more effectively mimic its service and methods of operations. Despite its efforts to protect its proprietary rights, attempts may be made to copy or reverse engineer aspects of FOXO’s products or services, or to obtain and use information that FOXO regards as proprietary and which a judge may not enjoin. Accordingly, FOXO may be unable to protect its proprietary rights against unauthorized third-party copying or use. Furthermore, as a practical matter, policing the unauthorized use of its intellectual property would be difficult for FOXO, because of the private nature of its competitors and because FOXO’s competitors may offer competing products as software-as-a-service, which may limit the ability to discover a competitor’s use of FOXO’s proprietary technology. Litigation may be necessary in the future to enforce its intellectual property rights, to protect its trade secrets, or to determine the validity and scope of the proprietary rights of others. Litigation and/or any of the events above could result in substantial costs and diversion of resources, and could have a material adverse impact on FOXO’s business, financial condition and results of operations.

FOXO may be unable to obtain sufficiently broad protection, or it may lose intellectual property protection.

As patent and trademark prosecution of biotechnology inventions is highly uncertain, involves complex legal and factual questions, and has been the subject of litigation in recent years, the issuance, scope, validity, enforceability and commercial value of FOXO’s intellectual property rights are highly uncertain. FOXO’s pending and future trademark or patent applications may not result in issued trademarks and patents that protect its products and services, which would render it unable to prevent others from commercializing the same or similar products and services that it offers. The coverage of trademark and patent claims may be significantly reduced before such intellectual property approval is granted and the scope and validity of issued trademarks and patents can also be challenged after grant, which, if successful, may not provide FOXO meaningful protection, may not allow it to exclude competitors or may not provide it with any competitive advantage.

Despite its efforts, FOXO may not be able to maintain confidentiality for its trade secrets and proprietary know-how. In addition, FOXO’s trade secrets and proprietary know-how may otherwise become known or be independently discovered by others. No guarantee can be given that others will not independently develop substantially equivalent proprietary information or techniques, or otherwise gain access to FOXO’s proprietary technology. FOXO relies on a combination of patent, trademark, and trade secret protection to establish and protect the ideas, concepts, and know-how for the products, services and technology it develops. FOXO’s failure to establish patent, trademark and trade secret protection for its technology and intellectual property rights could enable its competitors to more effectively compete and have an adverse impact on FOXO’s business, financial condition and results of operations.

FOXO may not be able to protect its intellectual property rights throughout the world.

Filing, prosecuting and defending trademarks or future patents on FOXO’s products and services in all countries throughout the world would be prohibitively expensive. In addition, the laws of some foreign countries do not protect intellectual property rights to the same extent as the laws of the United States, and FOXO may encounter difficulties in protecting and defending such rights in foreign jurisdictions. FOXO’s owned and licensed patent applications are

pending in the U.S. only and thus these present patent applications, even if granted, cannot cover any foreign countries in the future. Consequently, FOXO may not be able to prevent third parties from practicing its inventions in all countries outside the United States, or from selling or importing products made using its inventions in and into the United States or other jurisdictions. Competitors may use FOXO’s technologies (even copying from the patent disclosures) in jurisdictions where FOXO has not obtained patent protection to develop their own products and may also export infringing products to territories where FOXO has patent protection. These products may compete with FOXO’s products and its patents or other intellectual property rights may not be effective or sufficient to prevent them from competing.

Many companies have encountered significant problems in protecting and defending intellectual property rights in various foreign jurisdictions. The legal systems of many other countries do not favor the enforcement of patents and other intellectual property protection, particularly those relating to biotechnology, which could make it difficult for FOXO to stop the infringement of its patents in such countries. Proceedings to enforce FOXO’s current trademark and potential future patent rights in foreign jurisdictions could result in substantial cost and divert its efforts and attention from other aspects of its business, could put its intellectual property at risk of not issuing, being invalidated, or interpreted narrowly, and could provoke third parties to assert claims against FOXO. FOXO may not prevail in any lawsuits that it initiates and the damages or other remedies awarded, if any, may not be commercially meaningful. Accordingly, FOXO’s efforts to enforce its intellectual property rights around the world may be inadequate to obtain a significant commercial advantage from the intellectual property that it develops or licenses.

Changes in trademark or patent law in the United States and other jurisdictions could diminish the value of FOXO’s potential future trademarks and patents in general, thereby adversely impacting FOXO’s ability to protect its products and services.

Changes in either the trademark or patent laws or in interpretations of trademark or patent laws in the United States or other countries or regions may diminish the value of FOXO’s intellectual property. FOXO cannot predict the breadth of claims that may be allowed or enforced in its potential future trademarks and patents or in third-party intellectual property. In the United States, prior to March 16, 2013, assuming that other requirements for patentability were satisfied, the first to invent the claimed invention was entitled to the patent, while outside the United States, the first to file a patent application was entitled to the patent. On or after March 16, 2013, under the Leahy-Smith America Invents Act (or the America Invents Act), enacted on September 16, 2011, the United States transitioned to a first inventor to file system in which, assuming that other requirements for patentability are satisfied, the first inventor to file a patent application will be entitled to the patent on an invention regardless of whether a third party was the first to invent the claimed invention. As such, a third party that files a patent application in the United States Patent and Trademark Office (or the USPTO) before FOXO could be awarded a patent covering an invention of ours even if FOXO had made the invention before it was made by such third party. This will require FOXO to be cognizant of the time from invention to filing of a patent application. Since patent applications in the United States and most other countries are confidential for a period of time after filing or until issuance, FOXO cannot be certain that FOXO or its licensors were the first to either file any patent application related to its products or services, or invent any of the inventions claimed in its or its licensor’s patents or patent applications.

The America Invents Act also includes a number of significant changes that affect the way patent applications will be prosecuted and also may affect patent litigation. These include allowing third-party submission of prior art to the USPTO during patent prosecution and additional procedures to attack the validity of a patent by USPTO-administered post-grant proceedings, including post-grant review, inter partes review, and derivation proceedings. Because of a lower evidentiary standard in USPTO proceedings compared to the evidentiary standard in U.S. federal courts necessary to invalidate a patent claim, a third party could potentially provide evidence in a USPTO proceeding sufficient for the USPTO to hold a claim invalid even though the same evidence would be insufficient to invalidate the claim if first presented in a district court action. Accordingly, a third party may attempt to use the USPTO procedures to invalidate FOXO’s patent claims that would not have been invalidated if first challenged by the third party as a defendant in a district court action. Therefore, the America Invents Act and its implementation could increase the uncertainties and costs surrounding the prosecution of FOXO’s owned or in-licensed patent applications and the enforcement or defense of its owned or in-licensed issued patents, all of which could have a material adverse impact on FOXO’s business.

Recent U.S. Supreme Court rulings have also narrowed the scope of patent protection available in specific circumstances (e.g., regarding domestic processes) and weakened the rights of patent owners in certain situations. In addition to increasing uncertainty with regard to FOXO’s ability to obtain patents in the future, this combination of events has created uncertainty with respect to the value of patents, once obtained. Depending on decisions by the U.S. Congress, the federal courts and the USPTO, the laws and regulations governing patents could change in unpredictable ways that would weaken FOXO’s ability to obtain new patents or to enforce its existing patents and patents that it might obtain in the future.

FOXO may be subject to claims that its employees, consultants or independent contractors have wrongfully used or disclosed confidential information of third parties or that its employees have wrongfully used or disclosed alleged trade secrets of their former employers.

FOXO has employed and expects to employ or contract with individuals who were previously employed by or were independent contractors for universities or other companies, including FOXO’s competitors or potential competitors. Although FOXO tries to ensure that its employees, consultants and independent contractors do not use the proprietary information or know-how of others in their work for FOXO, FOXO may be subject to claims that its employees, consultants or independent contractors have inadvertently or otherwise used or disclosed trade secrets or other proprietary information of their former employers or other third parties, or to claims that FOXO has improperly used or obtained such trade secrets. Litigation may be necessary to defend against these claims. If FOXO fails in defending such claims, in addition to paying monetary damages, FOXO may lose valuable intellectual property rights or personnel, or lose the ability to use certain technologies, all of which could adversely impact its business. A loss of use of certain technologies or key research personnel work product could hamper or prevent FOXO’s ability to commercialize potential products and services, which could harm its business. Even if FOXO is successful in defending against these claims, litigation could result in substantial costs and be a distraction to management and other employees.

FOXO may not be successful in registering and enforcing its trademarks.

As FOXO applies to register its unregistered trademarks in the United States and other countries, its applications may not be allowed for registration in a timely fashion or at all, and its registered trademarks may not be maintained or enforced. Trademark enforcement is always uncertain, since proving infringement requires a showing of consumer confusion in addition to use by the defendant of a similar or identical trademark. In addition, opposition or cancellation proceedings may be filed against FOXO’s trademark applications and registrations, and its trademarks may not survive such proceedings. In certain countries outside of the United States, trademark registration is required to enforce trademark rights. If FOXO does not secure registrations for its trademarks, FOXO may encounter more difficulty in enforcing them against third parties than it otherwise would.

FOXO may be subject to claims challenging the inventorship or ownership of its patents and other intellectual property.

FOXO may be subject to claims that former employees, collaborators or other third parties have an interest in its future owned or in-licensed patents, trade secrets or other intellectual property as an inventor or co-inventor. Ownership disputes may arise, for example, from conflicting obligations of employees, consultants or others who are involved in developing its future products and services.

Litigation may be necessary to defend against these and other claims by a third party challenging inventorship of FOXO’s or its licensors’ ownership of its future owned or in-licensed patents, trade secrets or other intellectual property. If FOXO or its licensors fail in defending any such claims, in addition to paying monetary damages, FOXO may lose valuable intellectual property rights, such as exclusive ownership of, or a right to use, intellectual property or technology that is important to its product or services. Alternatively, FOXO may need to obtain one or more additional licenses from certain third parties, which could be time-consuming and expensive and could result in substantial costs and diversion of resources and could have a material adverse effect on FOXO’s business. Even if FOXO is successful in defending against such claims, litigation could result in substantial costs and be a distraction to management and other employees. Any of the foregoing could have a material adverse impact on FOXO’s business, financial condition, and results of operations.

If FOXO becomes involved in trademark or patent litigation or other proceedings related to a determination of rights, it could incur substantial costs and expenses, substantial liability for damages or be required to stop its development and commercialization efforts of its products and services.

There is a substantial amount of litigation, both within and outside the United States, involving trademark, patent and other intellectual property rights in the insurance technology industry, including patent and trademark infringement lawsuits, declaratory judgment litigation and adversarial proceedings before the USPTO, including trademark oppositions and cancellations, and patent interferences, derivation proceedings, ex parte reexaminations, post-grant review and inter partes review, as well as corresponding proceedings in foreign courts and foreign patent offices.

FOXO may, in the future, become involved with litigation or actions at the USPTO or foreign patent offices with various third parties. FOXO expects that the number of such claims may increase as its industry expands, more trademarks and patents are issued, the number of products or services increases and the level of competition in its industry increases. Any

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

Defined terms included below shall have the same meaning as terms defined and included elsewhere in this joint proxy statement/consent solicitation statement/prospectus.

(Dollars in thousands, except per share data)

Introduction

The following unaudited pro forma condensed combined financial information presents the combination of financial information of Delwinds and FOXO. The following unaudited pro forma condensed combined financial information has been prepared in accordance with Article 11 of Regulation S-X, as amended by final rule, Release No. 33-10786 “Amendments to Financial Disclosures about Acquired and Disposed Businesses.” Specifically, Release No. 33-10786 requires that the pro forma condensed combined balance sheet and statements of operations must include and be limited to i) transaction accounting adjustments and ii) autonomous entity adjustments, if required, and optionally, management adjustments that capture synergies or dis-synergies from a business combination.

The following pro forma condensed combined balance sheet has been calculated assuming the Business Combination occurred on June 30, 2022. The following pro forma condensed combined statements of operations have been calculated assuming the Business Combination occurred on January 1, 2021 (the beginning of the fiscal year presented). We have concluded that no autonomous entity adjustments are required.

The unaudited pro forma condensed combined financial information does not purport to represent, and is not necessarily indicative of, the actual results of operations or financial condition had Delwinds and FOXO been combined during the periods presented in the unaudited pro forma condensed combined financial information and is not intended to project the future results of operations or financial condition that the Combined Company may achieve. The unaudited pro forma condensed combined financial information does not give effect to the potential impact of any anticipated synergies, operating efficiencies or cost savings that may result from the Business Combination, any integration costs or tax deductibility of transaction costs. Furthermore, the unaudited pro forma condensed combined statement of operations does not include certain nonrecurring charges and the related tax effects which result directly from the Business Combination as described in the notes to the unaudited pro forma condensed combined financial information.

Delwinds’ historical results reflect the unaudited balance sheet as of June 30, 2022, the unaudited statement of operations for the six months ended June 30, 2022 and the audited statement of operations as of and for the year ended December 31, 2021 prepared in accordance with GAAP. FOXO’s historical results reflect FOXO’s unaudited balance sheet as of June 30, 2022, the unaudited statement of operations for six months ended June 30, 2022, and the audited statement of operations for the year ended December 31, 2021 prepared in accordance with GAAP. The unaudited pro forma condensed combined financial information should be read in conjunction with the audited historical financial statements of each Delwinds and FOXO and the notes thereto, as well as the disclosures contained in the sections titled “Management’s Discussion and Analysis of Financial Condition and Results of Operations of Delwinds’’ and “Management’s Discussion and Analysis of Financial Condition and Results of Operations of FOXO.”

Description of the Business Combination

On February 24, 2022, Delwinds, Merger Sub, Sponsor, as Purchaser Representative, and FOXO entered into the Merger Agreement to effect the merger of Merger Sub with and into FOXO, with FOXO as the continuing company. The aggregate consideration at the closing of the Business Combination to the stockholders of FOXO in the form of Class A Common Stock will be (a) $300,000, minus (b) the amount of closing indebtedness (excluding the FOXO Convertible Debt converted into shares of FOXO Class A common stock), minus (c) Excess Transaction Expenses, minus (d) an amount equal to the Management Contingent Shares multiplied by $10.00, with outstanding options and warrants to purchase shares of FOXO Class A common stock to be assumed by Delwinds and converted into the Assumed Options and Assumed Warrants.

The following summarizes the pro forma common stock ownership on June 30, 2022 (but taking into account the subsequent redemptions by Delwinds’ Public Stockholders in connection with the Extension Meeting on June 6, 2022) assuming (i) no further Public Stockholders of Delwinds exercise redemption rights, and (ii) Public Stockholders holding 11,047,578 of Delwinds’ public shares exercise their redemption rights in connection with the Closing for aggregate proceeds of $111,636.

All of the relative percentages above are for illustrative purposes only and are based upon certain assumptions as described in the section entitled “Frequently Used Terms — Share Calculations and Ownership Percentages.” Additionally, the relative percentages above assume that the Business Combination and related transactions were consummated on June 30, 2022. Should one or more of the assumptions prove incorrect, actual ownership percentages may vary materially from those described in this joint proxy statement/consent solicitation statement/prospectus as anticipated, believed, estimated, expected or intended.

Accounting for the Business Combination

Under applicable accounting standards, FOXO has been determined to be the accounting acquirer in the Business Combination, which will be treated as a reverse recapitalization. Under this method of accounting, although Delwinds will acquire all of the outstanding equity interests of FOXO in the Business Combination, Delwinds will be treated as the “acquired” company and FOXO will be treated as the accounting acquirer for financial statement reporting purposes. Accordingly, the Business Combination will be treated as the equivalent of FOXO issuing stock for the net assets of Delwinds, accompanied by a recapitalization. The net assets of Delwinds will be stated at historical cost, with no goodwill or other intangible assets recorded. Operations prior to the Business Combination will be those of FOXO.

Management considered the following predominant quantitative and qualitative factors in the determination that FOXO is the accounting acquirer in the Business Combination:

•        FOXO’s existing stockholders will have the greatest voting interest in the Combined Company;

•        FOXO’s existing stockholders will have the ability to control decisions regarding election and removal of directors and officers of the Combined Company;

•        FOXO’s existing senior management will be the senior management of the Combined Company; and

•        FOXO will comprise the ongoing operations of the Company.

The unaudited pro forma condensed combined financial information has been prepared using the assumptions below with respect to the potential redemption for cash of Delwinds’ common stock:

•        Assuming No Further Redemptions:    This presentation assumes that no Public Stockholders of Delwinds exercise redemption rights with respect to their Public Shares (but taking into account the subsequent redemptions by Delwinds’ Public Stockholders in connection with the Extension Meeting on June 6, 2022).

•        Assuming Maximum Redemptions:    This presentation assumes that the remaining 11,047,578 Public Shares are redeemed for aggregate redemption payments of $111,636 assuming a $10.105 per share Redemption Price based on funds in the Trust Account, including $0.105 per share that has been paid to