8-K

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): December 29, 2004

Critical Path, Inc.

(Exact name of registrant as specified in its charter)

California	000-25331	91-1788300
(State or other jurisdiction of incorporation)	(Commission File Number)	(IRS Employer Identification No.)

350 The Embarcadero, San Francisco, CA	94105
(Address of principal executive offices)	(Zip Code)

(415) 541-2500

(Registrant’s telephone number, including area code)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instruction A.2. below):

¨ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

¨ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

¨ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

¨ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Item 1.01 Entry into a Material Definitive Agreement.

On December 29, 2004, Critical Path, Inc. (the “Company”) entered into a Note and Warrant Purchase Agreement (the “Purchase Agreement”) with certain accredited investors (the “Investors”). Under the Purchase Agreement, the Company agreed to issue, in two closings, unsecured promissory notes (the “Notes”) having an aggregate principal balance of $18,000,000, together with warrants (the “Warrants”) to purchase an aggregate of 385,710 shares of Series F Redeemable Convertible Preferred Stock (the “Series F Preferred Stock”) at a per-share purchase price of $14.00 (equivalent to $1.40 per share on a common equivalent basis).

On December 30, 2004, the Company received aggregate proceeds of $11,000,000 in exchange for Notes issued to the Investors in the aggregate principal amount of $11,000,000 and Warrants to purchase 235,712 shares of Series F Preferred Stock. In March 2005, at the option of the Company, the Company will receive aggregate proceeds of $7,000,000 in exchange for additional Notes issued to the Investors in the aggregate principal amount of $7,000,000 and Warrants to purchase 149,998 shares of Series F Preferred Stock. The Company has also agreed to provide certain incidental registration rights to Richmond III (one of the Investors) with respect to shares of common stock issuable upon conversion of the Series F Preferred Stock issuable upon exercise of the Warrants.

The proceeds from the sale of the Notes will be used for working capital purposes. Investors in the above-described private placement are affiliates of General Atlantic Partners 74, L.P., a Delaware limited partnership, Campina Enterprises Limited (an affiliate of Cheung Kong (Holdings) Ltd) and Richmond III, LLC (an affiliate of Peter Kellner), each of which is a current shareholder of the Company.

A copy of the Purchase Agreement is filed as Exhibit 10.1 hereto and is incorporated herein by reference.

The Notes

Each Note issued will bear interest at thirteen and nine-tenths percent (13.9%) per annum. All payments under the Notes are deferred until maturity of the Notes or until they are otherwise due and payable. The outstanding principal amount and all accrued and unpaid interest on the Notes are due and payable on the earlier to occur of (i) maturity of the Notes, which is December 30, 2007, (ii) when declared due and payable upon the occurrence of an event of default or (iii) a change of control of the Company. The Company must also prepay the Notes in part under certain circumstances upon the sale of a business unit or division.

A copy of the form of Note is filed as Exhibit 4.1 hereto and is incorporated herein by reference.

The Warrants

The Warrants entitle the holders thereof to purchase shares of the Company’s Series F Preferred Stock until July 9, 2007 at an exercise price of $14.00 per share (equivalent to $1.40 per share on a common equivalent basis). The exercise price and the number of shares of Series F Preferred Stock issuable upon exercise of the Warrants is subject to adjustment upon certain events such as any dividend or distribution on the outstanding shares of Series F Preferred Stock or common stock of the Company or any subdivision, combination or reclassification of the Series F Preferred Stock.

A copy of the form of Warrant is filed as Exhibit 4.2 hereto and is incorporated herein by reference.

Series F Redeemable Convertible Preferred Stock

The Series F Preferred Stock will rank pari passu with Series E Redeemable Convertible Preferred Stock, and will rank senior to all other capital stock with respect to rights on liquidation, dissolution and winding up. The Series F Preferred Stock will accrue dividends at a simple annual rate of 5 ³/4% of the purchase price of $14.00 (equivalent to $1.40 per share on a common equivalent basis), whether or not declared by the board of directors. Dividends in respect of the Series F Preferred Stock will not be paid in cash but will be added to the value of the Series F Preferred Stock and will be taken into account for purposes of determining the liquidation and change in control preference, conversion rate and voting rights. The Company must declare or pay dividends on the Series F Preferred Stock when the Company declares or pay dividends to the holders of common stock. Holders of Series F Preferred Stock are entitled to notice of all shareholders’ meetings and are entitled to vote on all matters submitted to the

shareholders for a vote, voting together with the holders of the common stock and all other classes of capital stock entitled to vote, voting as a single class (except where a separate vote is required by the Company’s amended and restated articles of incorporation, its bylaws or California law). The holders of Series F Preferred Stock will be entitled to vote as a separate class on any amendment to the terms or authorized number of shares of Series F Preferred Stock, the issuance of any equity security ranking senior to the Series F Preferred Stock and the redemption of or the payment of a dividend in respect of any junior security. At any time, holders of Series F Preferred Stock may elect to convert their Series F Preferred Stock into common stock. Each share of Series F Preferred Stock is currently convertible into ten shares of common stock. After three years from the date the Series E Redeemable Convertible Preferred Stock is first issued, the Company may call for redemption of the Series F Preferred Stock under certain circumstances. On the fourth anniversary of the date the Series E Redeemable Convertible Preferred Stock is first issued, the Company must call for redemption of the Series F Preferred Stock.

A copy of the Certificate of Determination of Preferences of Series F Redeemable Convertible Preferred Stock is filed as Exhibit 3.1 hereto and incorporated herein by reference.

Preferred Stock Rights Agreement

On December 29, 2004, the Company and Computershare Trust Company, Inc. (“Computershare”) amended (“Amendment No. 6”) the Preferred Stock Rights Agreement dated as of March 19, 2001 between the Company and Computershare, as Rights Agent, as amended by Amendment No. 1, dated as of November 6, 2001 (“Amendment No. 1”), Amendment No. 2, dated as of November 18, 2003 (“Amendment No. 2”) and Amendment No. 3, dated as of January 16, 2004 (“Amendment No. 3”), and Amendment No. 4, dated as of March 9, 2004 (“Amendment No. 4”) and Amendment No. 5, dated as of June 24, 2004 (collectively, the “Rights Agreement”). The following paragraphs summarize the principal amendments to the Rights Agreement as effectuated by Amendment No. 1, Amendment No. 2, Amendment No. 3, Amendment No. 4, Amendment No. 5 and Amendment No. 6. Capitalized terms not defined herein have the meanings as set forth in the Rights Agreement.

Under Amendment No. 6, the definition of Acquiring Person was revised to exclude GAP Coinvestment Partners II, L.P., Cenwell Limited and Peter Kellner (an affiliate of Richmond III, LLC) as a result of the execution of that certain Note and Warrant Purchase Agreement, dated December 29, 2004, among the Company and the Purchasers named therein or as a result of any of the transactions contemplated by such agreement. A copy of Amendment No. 6 is filed as Exhibit 4.9 hereto and is incorporated herein by reference.

Item 2.03 Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant.

See Item 1.01 above.

Item 3.02 Unregistered Sales of Equity Securities.

See Item 1.01 above.

Item 3.03 Material Modification to Rights of Security Holders.

See Item 1.01 above.

Item 5.03 Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year.

On December 29, 2004, in connection with the sale and issuance of the Notes and Warrants, the Company amended its Amended and Restated Articles of Incorporation by filing a Certificate of Determination of Preference of Series F Redeemable Convertible Preferred Stock, in the form attached to this report. For a summary of the certificate of determination, see Items 1.01 and 3.02.

A copy of the Certificate of Determination of Preferences of Series F Redeemable Convertible Preferred Stock is filed as Exhibit 3.1 hereto and incorporated herein by reference.

Item 9.01 Financial Statements and Exhibits

EXHIBIT NO.	DESCRIPTION OF DOCUMENT
3.1*	Certificate of Determination of Preferences of Series F Redeemable Convertible Preferred Stock.
4.1*	Form of Note dated as of December 30, 2004.
4.2*	Form of Warrant to Purchase Series F Redeemable Convertible Preferred Stock of the Company dated December 30, 2004.
4.3	Preferred Stock Rights Agreement dated as of March 19, 2001 between Critical Path, Inc. and Computershare Trust Company, Inc., including the Certificate of Determination, the form of Rights Certificate and the Summary of Rights attached thereto as Exhibits A, B and C, respectively (filed as Exhibit 4.5 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.4	Amendment No. 1 to Preferred Stock Rights Agreement dated as of November 6, 2001 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.2 to Amendment No. 1 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.5	Amendment No. 2 to Preferred Stock Rights Agreement dated as of November 18, 2003 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.3 to Amendment No. 1 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.6	Amendment No. 3 to Preferred Stock Rights Agreement dated as of January 16, 2004 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.4 to Amendment No. 1 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.7	Amendment No. 4 to Preferred Stock Rights Agreement dated as of March 9, 2004 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.5 to Amendment No. 2 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.8	Amendment No. 5 to Preferred Stock Rights Agreement dated as of June 24, 2004 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.6 to Amendment No. 3 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.9*	Amendment No. 6 to Preferred Stock Rights Agreement dated as of December 29, 2004, between the Company and Computershare Trust Company, Inc.
10.1*	Note and Warrant Purchase Agreement dated as of December 29, 2004, between the Company and the Investors.

* filed herewith

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

Critical Path, Inc.
By:	/s/ Michael J. Zukerman
	Michael J. Zukerman
	Executive Vice President, General Counsel and Secretary

Date: January 3, 2004

Index to Exhibits

EXHIBIT NO.	DESCRIPTION OF DOCUMENT
3.1*	Certificate of Determination of Preferences of Series F Redeemable Convertible Preferred Stock.
4.1*	Form of Note dated as of December 30, 2004.
4.2*	Form of Warrant to Purchase Series F Redeemable Convertible Preferred Stock of the Company dated December 30, 2004.
4.3	Preferred Stock Rights Agreement dated as of March 19, 2001 between Critical Path, Inc. and Computershare Trust Company, Inc., including the Certificate of Determination, the form of Rights Certificate and the Summary of Rights attached thereto as Exhibits A, B and C, respectively (filed as Exhibit 4.5 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.4	Amendment No. 1 to Preferred Stock Rights Agreement dated as of November 6, 2001 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.2 to Amendment No. 1 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.5	Amendment No. 2 to Preferred Stock Rights Agreement dated as of November 18, 2003 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.3 to Amendment No. 1 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.6	Amendment No. 3 to Preferred Stock Rights Agreement dated as of January 16, 2004 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.4 to Amendment No. 1 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.7	Amendment No. 4 to Preferred Stock Rights Agreement dated as of March 9, 2004 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.5 to Amendment No. 2 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.8	Amendment No. 5 to Preferred Stock Rights Agreement dated as of June 24, 2004 between Critical Path, Inc. and Computershare Trust Company, Inc., as Rights Agent (filed as Exhibit 4.6 to Amendment No. 3 to the Company’s Registration Statement on Form 8-A (File No. 000-25331) and incorporated herein by reference).
4.9*	Amendment No. 6 to Preferred Stock Rights Agreement dated as of December 29, 2004, between the Company and Computershare Trust Company, Inc.
10.1*	Note and Warrant Purchase Agreement dated as of December 29, 2004, between the Company and the Investors.

* filed herewith

EX-3.1

Exhibit 3.1

CERTIFICATE OF DETERMINATION OF PREFERENCES OF

SERIES F REDEEMABLE CONVERTIBLE PREFERRED STOCK,

PAR VALUE $0.001 PER SHARE, OF

CRITICAL PATH, INC.,

a California corporation

Pursuant to Section 401 of the California Corporations Code,

The undersigned, Mark J. Ferrer and Michael J. Zukerman, do hereby certify that:

They are the duly elected and acting Chief Executive Officer and Executive Vice President, General Counsel and Secretary, respectively, of Critical Path, Inc., a California corporation (the “Corporation”).

Pursuant to authority given in the Corporation’s Amended and Restated Articles of Incorporation, the following recitals and resolutions, creating a series of four hundred fifty thousand (450,000) shares of Series F Redeemable Convertible Preferred Stock were duly adopted by the Corporation’s Board of Directors on December 16, 2004.

WITNESSETH

WHEREAS, the Board of Directors is authorized, within the limitations and restrictions stated in the Amended and Restated Articles of Incorporation of the Corporation, to provide by resolution or resolutions for the issuance of shares of Preferred Stock, par value $0.001 per share, of the Corporation, in one or more classes or series with such voting powers, full or limited, or no voting powers, and such designations, preferences and relative, participating, optional or other special rights, and qualifications, limitations or restrictions as shall be stated and expressed in the resolution or resolutions providing for the issuance thereof adopted by the Board of Directors, and as are not stated and expressed in the Amended and Restated Articles of Incorporation, or any amendment thereto, including (but without limiting the generality of the foregoing) such provisions as may be desired concerning voting, redemption, dividends, dissolution or the distribution of assets and such other subjects or matters as may be fixed by resolution or resolutions of the Board of Directors under the California Corporations Code; and

WHEREAS, it is the desire of the Board of Directors, pursuant to its authority as aforesaid, to authorize and fix the terms of a series of Preferred Stock and the number of shares constituting such series:

NOW, THEREFORE, BE IT RESOLVED:

1. Designation and Number of Shares. There shall be hereby created and established a series of Preferred Stock designated as “Series F Redeemable Convertible Preferred Stock” (the “Series F Preferred Stock”). The authorized number of shares of Series F Preferred

Stock shall four hundred fifty thousand (450,000). Capitalized terms used herein and not otherwise defined shall have the meanings set forth in Section 10 below.

2. Rank. The Series F Preferred Stock shall with respect to the payment of the Series F Liquidation Payment in the event of Liquidation or Change of Control and with respect to dividend and redemption rights rank (i) pari passu with the Series E Preferred Stock and (ii) senior to (A) all series of common stock of the Corporation (including, without limitation, the Common Stock, par value $0.001 per share, of the Corporation (the “Common Stock”)), (B) all series of preferred stock of the Corporation other than the Series E Preferred Stock (including, without limitation, the Series C Participating Preferred Stock, par value $0.001 per share, and the Series D Preferred Stock) and (C) each other class or series of Capital Stock of the Corporation hereafter created which does not expressly rank pari passu with or senior to the Series F Preferred Stock (clauses (A), (B) and (C), together, the “Junior Stock”).

3. Dividends.

(a) Dividend Rate. The holders of shares of Series F Preferred Stock shall accrue dividends at an annual rate equal to five and three-fourths percent (5¾%) of the Series F Price Per Share, calculated on the basis of a 360-day year, consisting of twelve 30-day months, and shall accrue on a daily basis from the date of issuance thereof, whether or not the Corporation has earnings or profits, whether or not there are funds legally available for the payment of dividends and whether or not declared by the Board of Directors. Such dividends shall not be paid in cash and shall instead be added to the Series F Accreted Value on a semi-annual basis on December 31^st and June 30^th of each year (each such date, a “Series F Accrual Date”). In addition, if the Corporation declares and pays any dividends on the Common Stock, then, in that event, the holders of shares of Series F Preferred Stock shall be entitled to share in such dividends on a pro rata basis, as if their shares had been converted into shares of Common Stock pursuant to Section 7(a) below immediately prior to the record date for determining the stockholders of the Corporation eligible to receive such dividends.

(b) Other Dividends. The Corporation shall not declare or pay any dividends on, or make any other distributions with respect to or redeem, purchase or otherwise acquire for consideration, any other shares of Capital Stock unless and until all accrued and unpaid dividends on the Series F Preferred Stock have been paid in full. Notwithstanding Section 2 or this Section 3(b), dividends shall accrue on the Series D Preferred Stock as provided in Section 3 of the Amended and Restated Series D Certificate of Determination and on the Series E Preferred Stock as provided in Section 3 of the Series E Certificate of Determination.

4. Liquidation and Change of Control.

(a) Series F Liquidation Payment. Upon the occurrence of a Liquidation, the holders of shares of Series F Preferred Stock shall be paid in cash for each share of Series F Preferred Stock held thereby, out of, but only to the extent of, the assets of the Corporation legally available for distribution to its stockholders, an amount equal to the greater of (i) the sum of (A) the Series F Accreted Value of such share of Series F Preferred Stock on the date of such Liquidation plus (B) all dividends accrued since the previous Series F Accrual Date or (ii) the aggregate consideration that would be paid to the holder of the number of shares of Common

2

Stock into which such share of Series F Preferred Stock is convertible immediately prior to such Liquidation. If the assets of the Corporation available for distribution to the holders of shares of Series F Preferred Stock shall be insufficient to permit payment in full to such holders of the sums which such holders are entitled to receive in such case, then all of the assets available for distribution to holders of shares of Series F Preferred Stock shall be distributed among and paid to such holders ratably in proportion to the amounts that would be payable to such holders if such assets were sufficient to permit payment in full.

(b) Change of Control. In the event of a Change of Control, the holders of shares of Series F Preferred Stock shall be paid for each share of Series F Preferred Stock held thereby, an amount equal to the greater of (i) the sum of (A) the Series F Accreted Value of such share of Series F Preferred Stock on the date of such Change of Control plus (B) all dividends accrued since the previous Series F Accrual Date or (ii) the aggregate consideration that would be paid to the holder of the number of shares of Common Stock into which such share of Series F Preferred Stock is convertible immediately prior to the closing of such Change of Control. Such amount shall be paid in the form of consideration paid in such Change of Control on the closing date of such Change of Control.

5. Redemption.

(a) Optional Redemption.

(i) Series F Optional Redemption Period. The Corporation shall not have any right to redeem any shares of the Series F Preferred Stock on or prior to the third anniversary of the Series E Closing Date. If on any date after the third anniversary of the Series E Closing Date, but prior to the Series F Automatic Redemption Date, the average closing price per share of the Common Stock, as reported on NASDAQ or other nationally recognized securities exchange on which the shares of Common Stock trade, for any sixty (60) consecutive trading days after such third anniversary date, equals or exceeds four hundred percent (400%) of the Series F Accreted Value (the “Series F Optional Redemption Measurement Window”), the Corporation shall have the right, at its sole option and election, to redeem (unless otherwise prevented by law) within thirty (30) days following such Series F Optional Redemption Measurement Window (the “Series F Optional Redemption Period”), all, but not less than all, of the outstanding shares of Series F Preferred Stock in cash, at a price per share (the “Series F Optional Redemption Price”) equal to the sum of the Series F Accreted Value plus all dividends accrued since the previous Series F Accrual Date.

(ii) Optional Redemption Payment. Written notice of any election by the Corporation to redeem the shares of Series F Preferred Stock pursuant to Section 5(a) (with a closing date prior to the expiration of the Series F Optional Redemption Period selected for such redemption (the “Series F Optional Redemption Date”)), shall be delivered in person, mailed by certified mail, return receipt requested, mailed by overnight mail or sent by telecopier not less than ten (10), nor more than thirty (30), days prior to such Series F Optional Redemption Date to the holders of record of the shares of Series F Preferred Stock, such notice to be addressed to each such holder at its address as shown in the records of the Corporation. The Series F Optional Redemption Price shall be made with respect to each share of Series F Preferred Stock by wire transfer of immediately available funds or check as promptly

3

as practicable and, in any event, within seven (7) days after receipt by the Corporation of the Series F Preferred Stock certificates to accounts designated in writing by the holders of such shares of Series F Preferred Stock (in the case of wire transfer) after surrender of the Series F Preferred Stock certificates pursuant to the following sentence. Upon notice from the Corporation, each holder of shares of Series F Preferred Stock so redeemed shall promptly surrender to the Corporation, at any place where the Corporation shall maintain a transfer agent for its shares of Series F Preferred Stock, certificates representing the shares so redeemed, duly endorsed in blank or accompanied by proper instruments of transfer. Notwithstanding anything to the contrary set forth in this Certificate of Determination, any holder of Series F Preferred Stock may convert its shares of Series F Preferred Stock pursuant to Section 7(a) until the Series F Optional Redemption Price has been paid in full by the Corporation to such holder.

(iii) Termination of Rights. If shares of Series F Preferred Stock are redeemed in full on the Series F Optional Redemption Date, then after the Series F Optional Redemption Date, all rights of any holder of shares of Series F Preferred Stock shall cease and terminate, and such shares of Series F Preferred Stock shall no longer be deemed to be outstanding; provided, however, that, if the Corporation defaults in the payment in full of the Series F Optional Redemption Price, then, subject to Section 5(b), the Corporation may not redeem the shares of Series F Preferred Stock until the next Series F Optional Redemption Measurement Window.

(b) Automatic Redemption.

(i) Automatic Redemption Date and Payment. On the fourth anniversary of the Series E Closing Date (the “Series F Automatic Redemption Date”), all of the shares of Series F Preferred Stock shall automatically, with no further action required to be taken by the Corporation or the holder thereof, be redeemed (unless otherwise prevented by law) in cash, at a redemption price per share (the “Series F Redemption Price”) equal to the sum of the Series F Accreted Value plus all dividends accrued since the previous Series F Accrual Date. Written notice of the Series F Automatic Redemption Date shall be delivered in person, mailed by certified mail, return receipt requested, mailed by overnight mail or sent by telecopier not less than thirty (30), nor more than sixty (60), days prior to the Series F Automatic Redemption Date to the holders of record of the shares of Series F Preferred Stock, such notice to be addressed to each such holder at its address as shown in the records of the Corporation. The Series F Redemption Price shall be made with respect to each share of Series F Preferred Stock by wire transfer of immediately available funds or check as promptly as practicable and, in any event, within seven (7) days after receipt by the Corporation of the Series F Preferred Stock certificates to accounts designated (in the case of wire transfer) in writing by the holders of such shares of Series F Preferred Stock after surrender of the Series F Preferred Stock certificates pursuant to the following sentence. Upon notice from the Corporation, each holder of such shares of Series F Preferred Stock so redeemed shall promptly surrender to the Corporation, at any place where the Corporation shall maintain a transfer agent for its shares of Series F Preferred Stock, certificates representing the shares so redeemed, duly endorsed in blank or accompanied by proper instruments of transfer. Notwithstanding anything to the contrary set forth in this Certificate of Determination, any holder of Series F Preferred Stock may convert its shares of Series F Preferred Stock pursuant to Section 7(a) hereof until the Series F Redemption Price has been paid in full by the Corporation to any such holder.

4

(ii) Termination of Rights. If the shares of Series F Preferred Stock are redeemed in full on the Series F Automatic Redemption Date, then after the Series F Automatic Redemption Date, all rights of any holder of such shares of Series F Preferred Stock shall cease and terminate, and such shares of Series F Preferred Stock shall no longer be deemed to be outstanding, whether or not the certificates representing such shares have been received by the Corporation; provided, however, that, if the Corporation defaults in the payment in full of the Series F Redemption Price, the rights of the holders of shares of Series F Preferred Stock shall continue until the Corporation cures such default.

(iii) Insufficient Funds for Redemption. If the funds of the Corporation available for redemption of the shares of Series F Preferred Stock on the Series F Automatic Redemption Date are insufficient to redeem in full the shares of Series F Preferred Stock, the holders of shares of Series F Preferred Stock shall share ratably in any funds available by law for redemption of such shares according to the respective amounts which would be payable with respect to the number of shares owned by them if the shares to be so redeemed on such Series F Automatic Redemption Date were redeemed in full. Any shares of Series F Preferred Stock that the Corporation does not redeem on the Series F Automatic Redemption Date due to insufficient funds shall continue to be outstanding until redeemed and dividends on such shares shall continue to accrue and cumulate until redeemed. The Corporation shall in good faith use all commercially reasonable efforts as expeditiously as possible to eliminate, or obtain an exception, waiver or exemption from, any and all restrictions that prevented the Corporation from paying the Series F Redemption Price and redeeming all of the shares of Series F Preferred Stock. At any time thereafter when additional funds of the Corporation are available by law for the redemption of the shares of Series F Preferred Stock, such funds shall be used as promptly as practicable to redeem the balance of such shares, or such portion thereof for which funds are available, on the basis set forth above.

6. Voting Rights.

(a) General. In addition to the voting rights to which the holders of Series F Preferred Stock are entitled under or granted by California law, the holders of Series F Preferred Stock shall be entitled to vote, in person or by proxy, at a special or annual meeting of stockholders on all matters entitled to be voted on by holders of shares of Common Stock voting together as a single class with the Common Stock (and with other shares entitled to vote thereon, if any), including, without limitation, the election of all of the directors of the Corporation (other than the director elected solely by the holders of the shares of Series D Preferred Stock pursuant to Section 6(b) of the Amended and Restated Series D Certificate of Determination). With respect to any such vote, each share of Series F Preferred Stock shall entitle the holder thereof to cast that number of votes as is equal to the quotient of (i) the sum of the Series F Accreted Value plus all dividends accrued since the previous Series F Accrual Date divided by (ii) the Series F Conversion Price as provided in Section 7(c) below.

(b) Series F Actions. At any meeting of the holders of shares of Series F Preferred Stock held for the purpose of voting upon any resolutions requiring the approval of the holders of shares of Series F Preferred Stock, voting as a separate class or series, the presence in person or by proxy of the holders of a majority of the shares of Series F Preferred Stock then outstanding shall constitute a quorum of the Series F Preferred Stock; the holders of shares of

5

Series F Preferred Stock shall be entitled to cast one vote per share of Series F Preferred Stock; and such resolution shall be deemed approved upon the affirmative vote of the holders of a majority of the outstanding shares of Series F Preferred Stock present in person or represented by proxy at such meeting.

(c) Action Without a Meeting. Except as provided in Section 305(b) and Section 603(d) of the California Corporations Code, any action required by the California Corporations Code to be taken at any annual or special meeting of holders of Series F Preferred Stock, voting as a separate class or series, may be taken without a meeting, without prior notice and without a vote, if a consent or consents in writing, setting forth the action so taken, shall be signed by the holders of outstanding shares of Series F Preferred Stock having not less than the minimum number of votes that would be necessary to authorize or take such action at a meeting of the holders of Series F Preferred Stock pursuant to Section 6(b) and shall be delivered (by hand or certified or registered mail, return receipt requested) to the Corporation by delivery to its registered office in the State of California, its principal place of business, or any officer or agent of the Corporation having custody of the book in which proceedings of meetings of the holders of Series F Preferred Stock are recorded. Every written consent shall bear the date of signature of each holder of Series F Preferred Stock who signs the consent. Prompt notice of the taking of the corporate action without a meeting by less than unanimous written consent shall, to the extent, required by applicable law, be given to those holders of Series F Preferred Stock who have not consented in writing, and who, if the action had been taken at a meeting, would have been entitled to notice of the meeting if the record date for such meeting had been the date that written consents signed by a sufficient number of holders to take the action were delivered to the Corporation.

(d) Major Actions. Notwithstanding anything to the contrary set forth in the Amended and Restated Articles of Incorporation or the By-laws of the Corporation, the affirmative vote of the holders of the outstanding shares of Series F Preferred Stock acting in accordance with Section 6(b) or 6(c), voting as a separate class, shall be a prerequisite to:

(i) any amendment to, restatement of or waiver of the terms of the Series F Preferred Stock, including, without limitation, by merger, consolidation, business combination or otherwise that is not a Change of Control;

(ii) the issuance, reservation for issuance or authorization of any Capital Stock of the Corporation or any right or option to acquire shares of Capital Stock ranking senior to the shares of Series F Preferred Stock or any increase or decrease in the authorized number of shares of Series F Preferred Stock; provided, that the Corporation may issue (A) options or shares pursuant to the Stock Option Plans, and (B) shares of Series F Preferred Stock issuable by the Corporation pursuant to agreements entered into prior to the Series F Closing Date;

(iii) the redemption of any Junior Stock other than the repurchase of unvested stock options or restricted stock from employees, officers, directors or consultants of the Corporation upon termination of service or in accordance with the Stock Option Plans;

6

(iv) prior to the payment in full of the Series F Liquidation Payment, any distribution or payment of any dividend or other distribution to any Junior Stock, provided that, no consent of the holders of Series F Preferred Stock shall be required for the accrual of dividends on the Series D Preferred Stock as provided in Section 3 of the Amended and Restated Certificate of Determination of Preferences of Series D Preferred Stock; and

(v) any amendment to this Section 6(d).

7. Conversion.

(a) Optional Conversion. Any holder of shares of Series F Preferred Stock shall have the right, at its option, at any time and from time to time, to convert, subject to the terms and provisions of this Section 7, any or all of such holder’s shares of Series F Preferred Stock into such number of fully paid and non-assessable shares of Common Stock as is equal to the product of (i) the number of shares of Series F Preferred Stock being so converted multiplied by (ii) the quotient of (x) the Series F Accreted Value divided by (y) the Series F Conversion Price, subject to adjustment as provided in Section 7(c) below. Such conversion right shall be exercised by the surrender of certificate(s) representing the shares of Series F Preferred Stock to be converted to the Corporation at any time during usual business hours at its principal place of business maintained by it (or such other office or agency of the Corporation as the Corporation may designate by notice in writing to the holders of shares of Series F Preferred Stock), accompanied by written notice that the holder elects to convert such shares of Series F Preferred Stock and specifying the name or names (with address) in which a certificate or certificates for shares of Common Stock are to be issued and (if so required by the Corporation) by a written instrument or instruments of transfer in form reasonably satisfactory to the Corporation duly executed by the holder or its duly authorized legal representative and transfer tax stamps or funds therefor, if required pursuant to Section 7(i) below. All certificates representing shares of Series F Preferred Stock surrendered for conversion shall be delivered to the Corporation for cancellation and canceled by it. As promptly as practicable after the surrender of any shares of Series F Preferred Stock, in any event within seven (7) days of the receipt of such certificates, the Corporation shall (subject to compliance with the applicable provisions of federal and state securities laws) deliver to the holder of such shares so surrendered certificate(s) representing the number of fully paid and nonassessable shares of Common Stock into which such shares are entitled to be converted. At the time of the surrender of such certificate(s), the Person in whose name any certificate(s) for shares of Common Stock shall be issuable upon such conversion shall be deemed to be the holder of record of such shares of Common Stock on such date, notwithstanding that the share register of the Corporation shall then be closed or that the certificates representing such Common Stock shall not then be actually delivered to such Person.

(b) Termination of Rights. On the date of such optional conversion pursuant to Section 7(a) above all rights with respect to the shares of Series F Preferred Stock so converted, including the rights, if any, to receive notices and vote, shall terminate, except only the rights of holders thereof to (i) receive certificates for the number of shares of Common Stock into which such shares of Series F Preferred Stock have been converted and (ii) exercise the rights to which they are entitled as holders of Common Stock.

7

(c) (i) Dividend, Subdivision, Combination or Reclassification of Common Stock. In the event that the Corporation shall at any time or from time to time after the date hereof, prior to conversion of shares of Series F Preferred Stock (w) pay a dividend or make a distribution on the outstanding shares of Common Stock payable in Capital Stock of the Corporation, (x) subdivide the outstanding shares of Common Stock into a larger number of shares, (y) combine the outstanding shares of Common Stock into a smaller number of shares or (z) issue any shares of its Capital Stock in a reclassification of the Common Stock (other than any such event for which an adjustment is made pursuant to another clause of this Section 7(c)), then, and in each such case, the Series F Conversion Price in effect immediately prior to such event shall be adjusted (and any other appropriate actions shall be taken by the Corporation) so that the holder of any share of Series F Preferred Stock thereafter surrendered for conversion shall be entitled to receive the number of shares of Common Stock or other securities of the Corporation that such holder would have owned or would have been entitled to receive upon or by reason of any of the events described above, had such share of Series F Preferred Stock been converted immediately prior to the occurrence of such event. An adjustment made pursuant to this Section 7(c)(i) shall become effective retroactively (x) in the case of any such dividend or distribution, to a date immediately following the close of business on the record date for the determination of holders of Common Stock entitled to receive such dividend or distribution or (y) in the case of any such subdivision, combination or reclassification, to the close of business on the day upon which such corporate action becomes effective.

(ii) Certain Distributions. In case the Corporation shall at any time or from time to time after the date hereof, prior to conversion of shares of Series F Preferred Stock, distribute to all holders of shares of the Common Stock (including any such distribution made in connection with a merger or consolidation in which the Corporation is the resulting or surviving Person and the Common Stock is not changed or exchanged) cash, evidences of indebtedness of the Corporation or another issuer, securities of the Corporation or another issuer or other assets (excluding cash dividends in which holders of shares of Series F Preferred Stock participate, in the manner provided in Section 3(b); dividends payable in shares of Common Stock for which adjustment is made under another paragraph of this Section 7(c); and any distribution in connection with an Excluded Transaction) or rights or warrants to subscribe for or purchase of any of the foregoing, then, and in each such case, the Series F Conversion Price then in effect shall be adjusted (and any other appropriate actions shall be taken by the Corporation) by multiplying the Series F Conversion Price in effect immediately prior to the date of such distribution by a fraction (x) the numerator of which shall be the Current Market Price of the Common Stock immediately prior to the date of distribution less the then fair market value (as determined by the Board of Directors in the exercise of their fiduciary duties) of the portion of the cash, evidences of indebtedness, securities or other assets so distributed or of such rights or warrants applicable to one share of Common Stock and (y) the denominator of which shall be the Current Market Price of the Common Stock immediately prior to the date of distribution (but such fraction shall not be greater than one); provided, however, that no adjustment shall be made with respect to any distribution of rights or warrants to subscribe for or purchase securities of the Corporation if the holder of shares of Series F Preferred Stock would otherwise be entitled to receive such rights or warrants upon conversion at any time of shares of Series F Preferred Stock into Common Stock. Such adjustment shall be made whenever any such distribution is made and shall become effective retroactively to a date immediately following the close of business on the record date for the determination of stockholders entitled to receive such distribution.

8

(iii) Other Changes. In case the Corporation at any time or from time to time after the date hereof, prior to the conversion of shares of Series F Preferred Stock, shall take any action affecting its Common Stock similar to or having an effect similar to any of the actions described in Sections 7(c)(i) or (ii) above or Section 7(f) below (but not including any action described in any such Section) and the Board of Directors shall consider whether an adjustment should thereupon be made in the Series F Conversion Price. If the Board of Directors in good faith determines that it would be equitable in the circumstances to adjust the Series F Conversion Price as a result of such action, then, and in each such case, the Series F Conversion Price shall be adjusted in such manner and at such time as the Board of Directors in good faith determines would be equitable in the circumstances (such determination to be evidenced in a resolution, a certified copy of which shall be mailed to the holders of shares of Series F Preferred Stock).

(iv) No Adjustment. Notwithstanding anything herein to the contrary, no adjustment under this Section 7(c) need be made to the Series F Conversion Price if the Corporation receives written notice from holders of a majority of the outstanding shares of Series F Preferred Stock that no such adjustment is required.

(d) Abandonment. If the Corporation shall take a record of the holders of its Common Stock for the purpose of entitling them to receive a dividend or other distribution, and shall thereafter and before the distribution to stockholders thereof legally abandon its plan to pay or deliver such dividend or distribution, then no adjustment in the Series F Conversion Price shall be required by reason of the taking of such record.

(e) Certificate as to Adjustments. Upon any adjustment in the Series F Conversion Price, the Corporation shall within a reasonable period (not to exceed ten (10) Business Days) following any of the foregoing transactions deliver to each registered holder of shares of Series F Preferred Stock a certificate, signed by (i) the Chief Executive Officer of the Corporation and (ii) the Chief Financial Officer of the Corporation, setting forth in reasonable detail the event requiring the adjustment and the method by which such adjustment was calculated and specifying the increased or decreased Series F Conversion Price then in effect following such adjustment.

(f) Reorganization, Reclassification. In case of any merger or consolidation of the Corporation (other than a Change of Control) or any capital reorganization, reclassification or other change of outstanding shares of Common Stock (other than a change in par value, or from par value to no par value, or from no par value to par value) after the date hereof (each, a “Transaction”), the holder of each share of Series F Preferred Stock shall have the right to receive in such Transaction, in exchange for each share of Series F Preferred Stock, a security identical to (and not less favorable than) the Series F Preferred Stock, and provision shall be made therefor in the agreement, if any, relating to such Transaction.

(g) Reservation of Common Stock. The Corporation shall at all times reserve and keep available for issuance upon the conversion of shares of Series F Preferred Stock, such number of its authorized but unissued shares of Common Stock as will from time to time be sufficient to permit the conversion of all outstanding shares of Series F Preferred Stock, and shall take all action to increase the authorized number of shares of Common Stock if at any time there

9

shall be insufficient authorized but unissued shares of Common Stock to permit such reservation or to permit the conversion of all outstanding shares of Series F Preferred Stock; provided, that the holders of shares of Series F Preferred Stock shall vote such shares in favor of any such action that requires a vote of stockholders.

(h) No Conversion Tax or Charge. The issuance or delivery of certificates for Common Stock upon the conversion of shares of Series F Preferred Stock shall be made without charge to the converting holder of shares of Series F Preferred Stock for such certificates or for any tax in respect of the issuance or delivery of such certificates or the securities represented thereby, and such certificates shall be issued or delivered in the respective names of, or (subject to compliance with the applicable provisions of federal and state securities laws) in such names as may be directed by, the holders of the shares of Series F Preferred Stock converted; provided, however, that the Corporation shall not be required to pay any tax which may be payable in respect of any transfer involved in the issuance and delivery of any such certificate in a name other than that of the holder of the shares of Series F Preferred Stock converted, and the Corporation shall not be required to issue or deliver such certificate unless or until the Person or Persons requesting the issuance or delivery thereof shall have paid to the Corporation the amount of such tax or shall have established to the reasonable satisfaction of the Corporation that such tax has been paid.

(i) Limitations on Conversions. Each holder of the Series F Preferred Stock’s right to convert its shares of Series F Preferred Stock into shares of Common Stock shall not be limited by any notice delivered by the Corporation of any proposed redemption, Change of Control or any other event that notwithstanding this subsection (i) shall purport to limit such conversion right.

8. Certain Remedies. Any registered holder of shares of Series F Preferred Stock shall be entitled to an injunction or injunctions to prevent breaches of the provisions of this Certificate of Determination and to enforce specifically the terms and provisions of this Certificate of Determination in any court of the United States or any state thereof having jurisdiction, this being in addition to any other remedy to which such holder may be entitled at law or in equity.

9. Business Day. If any payment shall be required by the terms hereof to be made on a day that is not a Business Day, such payment shall be made on the immediately succeeding Business Day.

10. Definitions. As used in this Certificate of Determination, the following terms shall have the following meanings (with terms defined in the singular having comparable meanings when used in the plural and vice versa), unless the context otherwise requires:

“Affiliate” shall mean any Person who is an “affiliate” as defined in Rule 12b-2 of the General Rules and Regulations under the Exchange Act.

“Amended and Restated Series D Certificate of Determination” means the Corporation’s Certificate of Determination of Preference of Series D Cumulative Redeemable Convertible Preferred Stock, as amended from time to time.

10

“Board of Directors” means the Board of Directors of the Corporation.

“Business Day” means any day except a Saturday, a Sunday, or other day on which commercial banks in the State of New York or the State of California are authorized or required by law or executive order to close.

“Capital Stock” means, with respect to any Person, any and all shares, interests, participations, rights in, or other equivalents (however designated and whether voting or non-voting) of, such Person’s capital stock (including, without limitation, common stock and preferred stock) and any and all rights, warrants or options exchangeable for or convertible into such capital stock.

“Certificate of Determination” means this Certificate of Determination of Preferences of Series F Redeemable Convertible Preferred Stock, as amended from time to time.

“Change of Control” means (i) any merger, consolidation or other business combination transaction (or series of related transactions) in which the stockholders owning a majority of the voting securities of the Corporation prior to such transaction do not own a majority of the voting securities of the surviving entity, (ii) any tender offer, exchange offer or other transaction whereby any person or “group” other than the Investors obtains a majority of the outstanding shares of capital stock entitled to vote in the election of the Board of Directors, (iii) any proxy contest in which a majority of the Board of Directors (or persons appointed by such Board of Directors) prior to such contest do not constitute a majority of the Board of Directors after such contest, (iv) a sale of all or substantially all of the assets of the Corporation or (v) ) any other transaction described in any stockholder rights agreement or “poison pill”, if any, to which the Corporation is party, which permits the holders of any rights or similar certificates to exercise the rights evidenced thereby and would require the Board of Directors to waive the application of such stockholder rights agreement or “poison pill” unless the Board of Directors has determined in good faith that such Person has inadvertently triggered such right

“Commission” means the United States Securities and Exchange Commission.

“Common Stock” shall have the meaning ascribed to it in Section 2 hereof.

“Common Stock Equivalent” shall mean any security or obligation which is by its terms convertible, exchangeable or exercisable into or for shares of Common Stock, including, without limitation, shares of Series D Preferred Stock, Series E Preferred Stock and Series F Preferred Stock and any option, warrant or other subscription or purchase right with respect to Common Stock or any Common Stock Equivalent.

“Corporation” shall have the meaning ascribed to it in the first paragraph of this Certificate of Determination.

“Current Market Price” per share of Capital Stock of any Person shall mean, as of the date of determination, (a) the average of the daily Market Price under clause (a), (b) or (c), as applicable, of the definition thereof of such Capital Stock during the immediately preceding thirty (30) trading days ending on such date, and (b) if such Capital Stock is not then listed or

11

admitted to trading on any national securities exchange or quoted in the over-the-counter market, then the Market Price under clause (d) of the definition thereof on such date.

“Exchange Act” means the Securities Exchange Act of 1934, as amended, and the rules and regulations of the Commission promulgated thereunder.

“Excluded Transaction” means (a) any issuance of shares of stock or options to purchase shares of Series F Preferred Stock, Series E Preferred Stock or Common Stock pursuant to the Stock Option Plans, (b) any issuance of Common Stock (i) upon the conversion of shares of Series F Preferred Stock, Series E Preferred Stock or Series D Preferred Stock, (ii) as a dividend on shares of Series F Preferred Stock, Series E Preferred Stock or Series D Preferred Stock or (iii) upon conversion or exercise of any Common Stock Equivalents, (c) any issuance of Common Stock in connection with any Series F Liquidation Payment, Series E Liquidation Payment or Series D Liquidation Payment, (d) Capital Stock issued in consideration of an acquisition, approved by the Board of Directors, of another Person, (e) shares of Common Stock and Common Stock Equivalents issued in strategic transactions (which may not be private equity or venture capital financing transactions), approved by the Board of Directors, to Persons that are not principally engaged in financial investing, and (f) shares of Series F Preferred Stock issuable pursuant to agreements entered into prior to the Series F Closing Date.

“GAAP” means United States generally accepted accounting principles in effect from time to time.

“Investors” means General Atlantic Partners 74, L.P., GAP Coinvestment Partners II, L.P., GapStar, LLC, GAPCO GmbH & Co. KG, Campina Enterprises Limited, and Richmond III, LLC and the Affiliates of the foregoing, provided that Affiliates shall be deemed not to include any portfolio companies of any of the foregoing.

“Junior Stock” shall have the meaning ascribed to it in Section 2(a) hereof.

“Liquidation” shall mean the voluntary or involuntary liquidation under applicable bankruptcy or reorganization legislation, or the dissolution or winding up of the Corporation.

“Market Price” shall mean, with respect to the Capital Stock of any Person, as of the date of determination, (a) if such Capital Stock is listed on a national securities exchange, the closing price per share of such Capital Stock on such date published in The Wall Street Journal (National Edition) or, if no such closing price on such date is published in The Wall Street Journal (National Edition), the average of the closing bid and asked prices on such date, as officially reported on the principal national securities exchange on which such Capital Stock is then listed or admitted to trading; or (b) if such Capital Stock is not then listed or admitted to trading on any national securities exchange but is designated as a national market system security by the National Association of Securities Dealers, Inc., the last trading price of such Capital Stock on such date; or (c) if there shall have been no trading on such date or if such Capital Stock is not designated as a national market system security by the National Association of Securities Dealers, Inc., the average of the reported closing bid and asked prices of such Capital Stock on such date as shown by the National Market System of the National Association of

12

Securities Dealers, Inc. Automated Quotations System and reported by any member firm of the New York Stock Exchange selected by the Corporation; or (d) if none of (a), (b) or (c) is applicable, the fair market value thereof as reasonably determined by the Board of Directors.

“NASDAQ” shall mean The Nasdaq Stock Market, Inc.

“Note and Warrant Purchase Agreement” means that certain Note and Warrant Purchase Agreement among the Corporation and certain of the Investors pursuant to which the Investors agreed to loan an aggregate of $18,000,000 to the Corporation.

“Person” means any individual, firm, corporation, partnership, limited liability company, trust, incorporated or unincorporated association, joint venture, joint stock company, governmental body or other entity of any kind.

“Securities Act” means the Securities Act of 1933, as amended, and the rules and regulations of the Commission promulgated thereunder.

“Series D Liquidation Payment” shall have the meaning ascribed to it in the Amended and Restated Certificate of Determination of Preferences of Series D Preferred Stock.

“Series D Preferred Stock” shall have the meaning ascribed to it in the Amended and Restated Certificate of Determination of Preferences of Series D Preferred Stock, as the same may be amended from time to time.

“Series E Closing Date” means July 9, 2004.

“Series E Preferred Stock” shall have the meaning ascribed to it in the Series E Certificate of Determination, as the same may be amended from time to time.

“Series E Certificate of Determination” means the Corporation’s Certificate of Determination of Preference of Series E Redeemable Convertible Preferred Stock, as the same may be amended from time to time.

“Series E Liquidation Payment” shall have the meaning ascribed to it in the Series E Certificate of Determination.

“Series F Accreted Value” shall mean as of any date, with respect to each share of Series F Preferred Stock, the Series F Price Per Share plus the amount of dividends that have accrued from the Series F Closing Date to the then most recent Series F Accrual Date pursuant to Section 3(a) of this Certificate of Determination.

“Series F Automatic Redemption Date” shall have the meaning ascribed to it in Section 5(b) hereof.

“Series F Closing Date” shall have the meaning ascribed to it in the Note and Warrant Purchase Agreement.

13

“Series F Conversion Price” shall mean the closing bid price of the Common Stock immediately preceding the execution of the Note and Warrant Purchase Agreement, as adjusted pursuant to Section 7(c). The dollar amount of the initial Series F Conversion Price is set forth in the Note and Warrant Purchase Agreement.

“Series F Liquidation Payment” shall mean, with respect to each share of Series F Preferred Stock, those amounts payable pursuant to Section 4(a)(i) or Section 4(b)(i), as the case may be.

“Series F Optional Redemption Date” shall have the meaning ascribed to it in Section 5(a)(ii) hereof.

“Series F Optional Redemption Measurement Window” shall have the meaning ascribed to it in Section 5(a)(i) hereof.

“Series F Optional Redemption Period” shall have the meaning ascribed to it in Section 5(a)(i) hereof.

“Series F Optional Redemption Price” shall have the meaning ascribed to it in Section 5(a)(i) hereof.

“Series F Preferred Stock” shall have the meaning ascribed to it in Section 1 hereof.

“Series F Price Per Share” shall mean the product of (i) the closing bid price of the Common Stock immediately preceding the execution of the Note and Warrant Purchase Agreement multiplied by (ii) ten (10) (subject to anti-dilution adjustment for stock splits of, combinations of and capital reorganizations with respect to the Series F Preferred Stock). The dollar amount of the initial Series F Price Per Share is set forth in the Note and Warrant Purchase Agreement.

“Series F Redemption Price” shall have the meaning ascribed to it in Section 5(b) hereof.

“Stock Option Plans” means the Corporation’s stock option plans and employee purchase plans approved by the Board of Directors, pursuant to which shares of restricted stock and options to purchase shares of Series F Preferred Stock, Series E Preferred Stock and/or Common Stock are reserved and available for grant to officers, directors, employees and consultants of the Corporation.

*****

14

This Certificate of Determination has been duly approved by the Board of Directors. The authorized number of shares of Preferred Stock of the Corporation is 75,000,000, of which one share constitutes the Special Voting Share, which share has been issued, 75,000 shares constitute Series C Participating Preferred Stock, none of which has been issued, 4,188,587 shares of Series D Preferred Stock, of which 4,102,355 shares are outstanding 68,000,000 shares of Series E Preferred Stock, of which 55,896,867 shares are outstanding, and 450,000 shares of Series F Preferred Stock, none of which has been issued. The number of shares voting in favor of this Certificate of Determination equaled or exceeded the vote required. The percentage vote required under the Amended and Restated Articles of Incorporation in effect at the time of this Certificate of Determination was more than 50% of the outstanding shares of Series D Preferred Stock, voting separately as a class.

[the remainder of this page intentionally left blank]

15

The undersigned, Mark J. Ferrer and Michael J. Zukerman, the Chief Executive Officer and Executive Vice President and Secretary, respectively, of Critical Path, Inc., declare under penalty of perjury that the matters set out in the foregoing Certificate are true of their own knowledge.

Executed at San Francisco, California on this 29 day of December, 2004.

/s/ Mark J. Ferrer

Mark J. Ferrer,

Chief Executive Officer

/s/ Michael J. Zukerman

Michael J. Zukerman,

Executive Vice President, General Counsel and Secretary

EX-4.1

Exhibit 4.1

THIS NOTE HAS BEEN ACQUIRED FOR INVESTMENT AND NOT WITH A VIEW TO, OR FOR SALE IN CONNECTION WITH, THE DISTRIBUTION THEREOF. THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY STATE SECURITIES LAWS, AND MAY NOT BE PLEDGED, SOLD, OFFERED FOR SALE, TRANSFERRED, OR OTHERWISE DISPOSED OF IN THE ABSENCE OF REGISTRATION UNDER OR EXEMPTION FROM SUCH ACT AND ALL APPLICABLE STATE SECURITIES LAWS.

CRITICAL PATH, INC.

PROMISSORY NOTE

$________________	San Francisco, California
	December 30, 2004

Critical Path, Inc., a California corporation (the “Company”), the principal office of which is located in San Francisco, California, for value received hereby promises to pay to the order of                                     , or its registered assigns (“Holder”), the sum of                                                   dollars ($                    ), or such lesser amount as shall then equal the outstanding principal amount hereof on the terms and conditions set forth hereinafter. The outstanding principal amount hereof and all accrued and unpaid interest hereon, as set forth below, shall be due and payable on the earlier to occur of (i) December 30, 2007, (ii) when declared due and payable by Holder upon the occurrence of an Event of Default or (iii) a Change of Control (the earliest of the events set forth in items (i)-(iii) immediately above, the “Maturity Date”). In addition, if the Company or any of its Subsidiaries consummates a Business Unit Sale resulting in proceeds to the Company and/or any of its Subsidiaries of less than forty million dollars ($40,000,000) but at least twenty million dollars ($20,000,000), then the Company shall pay (x) thirty-three percent (33%) of the Accreted Principal Amount, together with accrued and unpaid interest thereon since the most recent Interest Compounding Date, to the Holder from the first twenty million dollars ($20,000,000) of such proceeds and (y) from each incremental five million dollars ($5,000,000) of proceeds in excess of twenty million dollars ($20,000,000), sixteen and seventy-five one-hundredths percent (16.75%) of the unpaid Accreted Principal Amount, together with accrued and unpaid interest thereon since the most recent Interest Compounding Date, to the Holder from such proceeds immediately after the receipt of such proceed by the Company.

The Company may prepay this Note in cash in full at any time commencing on June 30, 2005 for an amount equal to the sum of (i) the Accreted Principal Amount of the Notes plus (ii) all accrued and unpaid interest thereon since the most recent Interest Compounding Date; provided, however, that if the Company wishes to prepay any of the Notes (including this Note) issued pursuant to the Note Purchase Agreement, then such prepayment(s) must be made pro rata with respect to all such Notes.

The following is a statement of the rights of the Holder of this Note and the conditions to which this Note is subject, and to which the Holder hereof, by the acceptance of this Note, agrees:

1. Definitions. Except as otherwise defined herein, each capitalized term used herein shall have the meaning assigned to it in the Note Purchase Agreement, as in effect on the date hereof, and without regard to any subsequent termination of the Note Purchase Agreement. All other references to the Note Purchase Agreement in this Note refer to the Note Purchase Agreement as in effect on the date hereof, and without regard to any subsequent termination of the Note Purchase Agreement. As used in this Note, the following terms, unless the context otherwise requires, have the following meanings:

1.1 “Accreted Principal Amount” shall have the meaning set forth in Section 2 hereof.

1.2 “Affiliate” means any Person who is an “affiliate” as defined in Rule 12b-2 of the General Rules and Regulations of the Securities Exchange Act of 1934, as amended.

1.3 “Business Unit Sale” means a sale by the Company or any of its Subsidiaries of any business unit.

1.4 “Capitalized Lease Obligations” means, with respect to any Person, all rental obligations of such Person which, under GAAP, are or will be required to be capitalized on the books of such Person, in each case taken at the amount thereof accounted for as indebtedness in accordance with such principles.

1.5 “Change of Control” shall mean (i) any merger, consolidation or other business combination transaction (or series of related transactions) in which the stockholders owning a majority of the voting securities of the Company prior to such transaction do not own a majority of the voting securities of the Company or the surviving entity, as the case may be, (ii) any tender offer, exchange offer or other transaction whereby any Person or “group” (as defined in Rule 13d-3 of the General Rules and Regulations of the Securities Exchange Act of 1934, as amended) other than the Investors obtains a majority of the outstanding shares of capital stock entitled to vote in the election of directors, (iii) a sale of all or substantially all of the Company’s assets or properties in one or a series of related transactions, (iv) a Business Unit Sale resulting in proceeds to the Company and/or any of its subsidiaries of at least forty million dollars ($40,000,000) or (v) any other transaction described in any stockholder rights agreement or “poison pill”, if any, to which the Company is party, which permits the holders of any rights or similar certificates to exercise the rights evidenced thereby and would require the Board of Directors to waive the application of such stockholder rights agreement or “poison pill” unless the Board of Directors has determined in good faith that such Person has inadvertently triggered such right.

2

1.6 “Company” shall have the meaning set forth in the recitals hereto, and includes any corporation that shall succeed to or assume the obligations of the Company under this Note.

1.7 “Domestic Subsidiary” shall have the meaning set forth in Section 3.8 hereof.

1.8 “Event of Default” shall have the meaning set forth in Section 4 hereof.

1.9 “GAP Entities” shall mean General Atlantic Partners 74, L.P., GAP Coinvestment Partners II, L.P., GapStar, LLC and GAPCO GmhH & Co. KG.

1.10 “Holder” shall mean the registered holder of this Note from time to time, and in the plural, shall mean all registered holders of Notes from time to time issued by the Company pursuant to the Note Purchase Agreement.

1.11 “Interest Compounding Date” shall have the meaning set forth in Section 2 hereof.

1.12 “Investment” means (i) the acquisition (whether for cash, property, services, assumption of Indebtedness, securities or otherwise) of assets (other than equipment, inventory, supplies or other assets acquired in the ordinary course of business of the Company), capital stock, bonds, notes, debentures, partnership, joint venture or other ownership interests or other securities of any Person, (ii) any deposit with, or advance, loan or other extension of credit to, or on behalf of, any Person (other than deposits made in connection with the purchase of equipment, inventory, services, leases, supplies or other assets in the ordinary course of business of the Company), and (iii) any other capital contribution to or investment in any Person, including, without limitation, any guaranty obligation incurred for the benefit of any Person. For the sake of clarity, Investments shall include any transfer of property or assets by the Company to any of its Subsidiaries or by any Subsidiary of the Company to any other Subsidiary.

1.13 “Note” shall mean this note, and in the plural, shall mean all notes issued to the Investors pursuant to the terms of the Note Purchase Agreement, including this Note, and all amendments, modifications and extensions thereto.

1.14 “Note Purchase Agreement” means that certain Note and Warrant Purchase Agreement, dated December 29, 2004, among the Company, the Holder and the other parties thereto from time to time, and all amendments, modifications and extensions thereto.

1.15 “Permitted Investments” means (i) Investments in cash or cash equivalents, (ii) accounts receivable created, acquired or made in the ordinary course of business and payable or dischargeable in accordance with customary trade terms; (iii) Investments existing on the closing date, and listed on Schedule 3.26 to the Note Purchase Agreement, (iv) loans to employees, directors or officers of the Company in connection with the award of convertible bonds or capital stock under a stock incentive

3

plan, stock option plan or other equity-based compensation plan or arrangement, (v) other advances or loans to employees, directors, officers or agents of the Company in the ordinary course of business not to exceed $500,000 in the aggregate at any time outstanding; (vi) loans, advances and investments in foreign Subsidiaries made after the date hereof (that are not incorporated or otherwise organized under the laws of the United States of America or any state thereof) in an amount not to exceed $1,000,000 in the aggregate at any time outstanding provided, however, that the foregoing shall not apply to loans, advances and investments in the Company’s Canadian Subsidiaries; (vii) any acquisition for which the prior written consent of the Holders of a majority of the outstanding principal amount of all of the Notes issued by the Company pursuant to the Note Purchase Agreement has been obtained, or (viii) other loans, advances and investments of a nature not contemplated by the foregoing sections in an amount not to exceed $500,000 in the aggregate at any time outstanding.

1.16 “Permitted Liens” shall have the meaning set forth in Section 3.3.

1.17 “Person” means any individual, firm, corporation, partnership, trust, joint venture, joint stock company, limited liability company, Governmental Authority or other entity of any kind, and shall include any successor (by merger or otherwise) of such entity.

1.18 “Restricted Payment” means (a) any dividend or other distribution (whether in cash, securities or other property) with respect to any shares of any class of capital stock of the Company or any of its Subsidiaries or (b) any payment (whether in cash, securities or other property), including any sinking fund or similar deposit, on account of the purchase, redemption, retirement, acquisition, cancellation or termination of any shares of any class of capital stock of the Company or any Subsidiary or any option, warrant or other right to acquire any such shares of capital stock of the Company or any Subsidiary.

1.19 “UCC” shall have the meaning set forth in Section 3.3.

2. Interest. Interest shall accrue at the rate of thirteen and nine-tenths percent (13.9%) per annum (or such lesser amount as shall equal the highest rate of interest allowable under applicable law) (the “Interest Rate”), on the outstanding Accreted Principal Amount (as hereinafter defined), from the date of this Note until the Maturity Date or the date this Note is otherwise repaid. The Company shall not be obligated to make any payments of interest which shall have accrued under this Note prior to the Maturity Date. Interest shall be calculated on the basis of a 365-day year for the actual number of days elapsed. Accrued interest shall compound to the Accreted Principal Amount on the last day of each calendar quarter from the date of this Note until the Maturity Date or the date this Note is otherwise repaid (each such quarterly date, the “Interest Compounding Date”). “Accreted Principal Amount” means the principal amount of the Notes plus the amount of interest that has accrued and compounded thereon on each Interest Compounding Date. In the event that the principal amount of this Note, any interest, or any amount payable hereunder is not paid in full when such

4

amount becomes due and payable, or upon the occurrence of an Event of Default, interest shall accrue at the lesser of (a) the initial Interest Rate plus five percent (5%) per annum or (b) the highest rate of interest allowable under applicable law, on the balance of all amounts outstanding until such overdue amounts are paid or the Event of Default is cured, and such interest shall be payable on demand.

3. Covenants. The Company covenants and agrees until the date on which all present and future obligations and liabilities of the Company to the Holder for the payment of money under this Note (extending to all principal amounts, interest, late charges, fees and all other charges and sums, as well as all costs and expenses payable by the Company under this Note, including interest accruing at the then applicable rate provided in this Note after the filing of any petition in bankruptcy, or the commencement of any insolvency, reorganization or like proceedings, relating to the Company, whether or not a claim for post-filing post-petition interest is allowed in such proceeding) have been paid in full:

3.1 Financial Statements and Other Information.

(a) The Company shall deliver to the Holder of this Note the financial statements and other information required to be delivered under Section 8.1 of the Note Purchase Agreement.

(b) Not later than 15 days after the end of each month, the Company will provide a statement of the Company’s results of operations (on an adjusted EBITDA basis) and capital expenditures for such preceding month, each compared to the Company’s annual operating budget.

3.2 Indebtedness. The Company shall not, and shall not permit any Subsidiary to, issue, incur, assume, create or have outstanding any Indebtedness; provided, however, that the foregoing shall not restrict nor operate to prevent:

(a) Indebtedness in favor of the Holders under this Note and the Note Purchase Agreement;

(b) Indebtedness existing on the date hereof, as set forth on Schedule 3.22 to the Note Purchase Agreement;

(c) Indebtedness for accounts payable incurred in the ordinary course of business by the Company;

(d) Indebtedness incurred solely for the purpose of financing the acquisition of any equipment, machinery, software, improvements or any other similar property, or extensions, renewals or replacements of any of the foregoing for the same or a lesser amount; provided, that the aggregate outstanding principal amount of all Indebtedness permitted pursuant to this clause (d) outstanding for more than sixty (60) days after the incurrence of such Indebtedness shall not at any time exceed $500,000;

5

(e) Indebtedness of the Company evidenced by Capitalized Lease Obligations, provided, that in no event shall the aggregate principal amount of Capitalized Lease Obligations permitted by this clause (e) exceed $500,000 at any time outstanding; and

(f) Any extension, renewal, refinancing, refunding, or replacement (each, a “refinancing”) of Indebtedness permitted by clauses (b) through (e) above, on such terms and conditions as are, on the whole, not materially more onerous to the Company than the terms and conditions of such original Indebtedness on the date of such refinancing (including that the principal amount of such refinancing Indebtedness does not exceed the principal amount of, plus the amount of accrued and unpaid interest on, the Indebtedness so refinanced (plus the amount of reasonable premium and fees and expenses incurred in connection therewith)).

3.3 Liens. The Company shall not, and shall not permit any of its Subsidiaries to, create, incur, assume or suffer to exist any Lien upon or with respect to any property or assets (real or personal, tangible or intangible) of the Company or any of its Subsidiaries, whether now owned or hereafter acquired, or sell any such property or assets subject to an understanding or agreement, contingent or otherwise, to repurchase such property or assets (including sales of accounts receivable), or assign any right to receive income or permit the filing of any financing statement under the Uniform Commercial Code, as from time to time in effect in the relevant jurisdiction (the “UCC”), or any other similar notice of Lien under any similar recording or notice statute; provided, that the provisions of this Section 3.3 shall not prevent the creation, incurrence, assumption or existence of the following:

(a) Liens arising in the ordinary course of business by statute in connection with worker’s compensation, unemployment insurance, old age benefits, social security obligations, statutory obligations or other similar charges (other then Liens arising under ERISA), good faith cash deposits in connection with tenders, contracts or leases to which the Company or any Subsidiary is a party or other cash deposits required to be made in the ordinary course of business, provided, that such Liens do not have a material adverse effect on the ability of the Company to repay amounts due under the Notes;

(b) inchoate Liens for taxes, assessments or governmental charges or levies not yet due or Liens for taxes, assessments or governmental charges or levies being contested in good faith and by appropriate proceedings for which adequate reserves have been established in accordance with GAAP;

(c) Liens in respect of property or assets of the Company or its Subsidiaries imposed by law, which were incurred in the ordinary course of business and do not secure Indebtedness for borrowed money, such as carriers’, warehousemen’s, materialmen’s and mechanics’ liens and other similar Liens arising in the ordinary course of business, and (i) which do not in the aggregate materially detract from the value of the Company’s and its Subsidiaries’ property or assets taken as a whole

6

or result in a material adverse effect on the Condition of the Company or (ii) which are being contested in good faith by appropriate proceedings, which proceedings have the effect of preventing the forfeiture or sale of the property or assets subject to any such Lien;

(d) the pledge of assets for the purpose of securing an appeal, stay or discharge in the course of any legal proceeding, provided that the aggregate amount of liabilities of the Company and its Subsidiaries secured by a pledge of assets permitted under this subsection, including interest and penalties thereon, if any, shall not be in excess of $500,000 at any one time outstanding;

(e) any interest or title of a lessor under any operating lease;

(f) easements, rights-of-way, restrictions and other similar encumbrances against real property incurred in the ordinary course of business;

(g) the Liens existing on the date hereof identified on Schedule 3.22 to the Note Purchase Agreement;

(h) Liens on cash deposited with account debtors to secure performance by the Company or any Subsidiary in the ordinary course of business subject to customary and reasonable terms;

(i) Liens upon assets of the Company or its Subsidiaries subject to Capitalized Lease Obligations, provided, that (A) such Liens only serve to secure the payment of Indebtedness permitted by Section 3.2(e) arising under such Capitalized Lease Obligation and (B) the Lien encumbering the asset giving rise to the Capitalized Lease Obligation does not encumber any other asset of the Company or its Subsidiaries;

(j) Liens placed upon equipment, machinery, software, improvements or any other similar property, used in the ordinary course of business of the Company or any of its Subsidiaries at the time of the acquisition thereof by the Company or any of its Subsidiaries or within ninety (90) days thereafter to secure Indebtedness permitted by Section 3.2(d) above; provided, that the Liens encumbering the equipment, machinery software, improvements or any other similar property so acquired do not encumber any other asset of the Company or its Subsidiaries; and

(k) set-off rights of depository institutions (collectively with clauses (a) through (k) hereof, the “Permitted Liens”).

3.4 Fundamental Changes. The Company will not (i) consummate any Change of Control, (ii) sell, transfer, lease or otherwise dispose of (in one transaction or a series of transactions) assets for a purchase price in excess of five million dollars ($5,000,000) or outside of the ordinary course of business (other than (A) sales or disposals of obsolete assets that the Company has determined, in good faith, not

7

to be useful in the conduct of its business or (B) a Business Unit Sale resulting in proceeds to the Company and/or any of its Subsidiaries of less than forty million dollars ($40,000,000), but at least twenty million dollars ($20,000,000)) or all or substantially all of the stock of any of its Subsidiaries (in each case, whether now owned or hereafter acquired), or (iii) liquidate or dissolve, except that, if at the time and immediately after giving effect thereto no Event of Default shall have occurred and be continuing, provided that (A) the Company or any of its Subsidiaries may, with the prior written consent of the Holders, merge with or into any other wholly-owned Subsidiary of the Company and, except as otherwise prohibited by this Note, may sell, transfer, lease or otherwise dispose of its assets to the Company or to another wholly-owned Subsidiary of the Company; and (B) any Subsidiary may liquidate or dissolve if the Board of Directors of the Company determines in good faith that such liquidation or dissolution is in its best interests and is not disadvantageous to the Holders.

3.5 Restricted Payments. The Company will not, and the Company will not permit any Subsidiary to, declare or make, or agree to pay or make, directly or indirectly, any Restricted Payment, except that (i) any Subsidiary may make a Restricted Payment to the Company or any of its wholly-owned Subsidiaries, and (ii) the Company or any of its Subsidiaries may make any Restricted Payment required by the terms of the Note Purchase Agreement and the other documents executed in connection therewith.

3.6 Transactions with Affiliates. The Company will not, and the Company will not permit any Subsidiary to, sell, lease or otherwise transfer any property or assets to, or purchase lease or otherwise acquire any property or assets from, or otherwise engage in any other transactions with, any of its Affiliates, except (a) transactions that are at prices and on terms and conditions not less favorable to the Company or such Subsidiary than could be obtained on an arm’s length basis from unrelated third parties, and (b) transactions under the agreements listed on Schedule 3.17 to the Note Purchase Agreement.

3.7 Investments. The Company will not, and the Company will not permit any Domestic Subsidiary (as hereinafter defined) to, make an Investment in any Person, except for Permitted Investments.

3.8 Property of Existing Domestic Subsidiaries. The Company will not permit, or suffer to allow, any Subsidiary that is incorporated or otherwise organized under the laws of the United States of America or any state thereof (a “Domestic Subsidiary”), to (i) own, hold, lease, license, purchase or otherwise acquire any personal or real property (excluding any material intellectual property) in excess of $50,000 for all property held by such Subsidiary, or $250,000 in the aggregate for all property held by all Domestic Subsidiaries (ii) maintain any deposit account in its name, (iii) own or otherwise hold any rights to any material intellectual property or (iv) otherwise conduct any business or maintain operations.

3.9 Books and Records. The Company shall not make any material changes in accounting policies and shall keep proper books of record and

8

account, in which full and correct entries shall be made of all financial transactions and the assets, liabilities and business of the Company and its Subsidiaries in accordance with GAAP consistently applied.

3.10 Inspection. The Company shall, and shall cause each of its Subsidiaries to, permit representatives of the Holders to visit and inspect any of its properties, to examine its corporate, financial and operating records and make copies thereof or abstracts therefrom, and to discuss its affairs, finances and accounts with their respective directors, officers and independent public accountants, all at such reasonable times during normal business hours and as often as may be reasonably requested upon notice to the Company.

3.11 Maintenance of Business. The Company shall, and shall cause each Subsidiary to, preserve and maintain its existence. The Company shall, and shall cause each Subsidiary to, preserve and keep in force and effect all licenses, permits, franchises, approvals, patents, trademarks, trade names, trade styles, copyrights, and other property rights necessary to the proper conduct of its business, except where the failure to do so could not reasonably be expected to have a material adverse effect on the Condition of the Company or on the prospects of repayment of the Notes.

3.12 Maintenance of Properties. The Company shall, and shall cause each Subsidiary to, maintain, preserve and keep its property and equipment in good repair, working order and condition (ordinary wear and tear excepted) and shall from time to time make all needful and proper repairs, renewals, replacements, additions and betterments thereto so that at all times the efficiency thereof shall by fully preserved and maintained, except in each case to the extent that, in the reasonable business judgment of such Person, any such property or equipment is no longer necessary for the proper conduct of the business of such Person.

4. Events of Default. The occurrence of any one or more of the following events shall constitute an “Event of Default”:

4.1 Failure To Pay. (i) The failure of the Company to pay any principal due under any of the Notes when due and payable (whether by acceleration, declaration, extension or otherwise), or (ii) the failure of the Company to pay any other amounts due under any of the Notes when due and payable if such failure is not cured within five (5) days of Company’s receipt of notice thereof from any of the Holders.

4.2 Other Covenants and Agreements. The failure of Company or any of its Subsidiaries to perform, observe or comply with any of the covenants of this Note and the Note Purchase Agreement, if such failure is not cured within sixty (60) days from its respective due date.

4.3 Representations and Warranties. If any representation or warranty made by the Company or any of its Subsidiaries in the Note Purchase Agreement is not true and correct in all material respects on the Initial Closing Date or the Second Closing Date, as the case may be.

9

4.4 Default on Other Obligations. The occurrence of any condition resulting in the acceleration of or default under any other Indebtedness for borrowed money of the Company or any of its Subsidiaries.

4.5 Involuntary Bankruptcy. There shall be filed against the Company or any of its Subsidiaries an involuntary petition or other pleading seeking the entry of a decree or order for relief under the United States Bankruptcy Code or any similar federal or state insolvency or similar laws ordering: (a) the liquidation of the Company or any of its Subsidiaries or (b) a reorganization of the Company or any of its Subsidiaries or the business and affairs of the Company or any of its Subsidiaries or (c) the appointment of a receiver, liquidator, assignee, custodian, trustee or similar official for the Company or any of its Subsidiaries of the property of the Company or any of its Subsidiaries.

4.6 Voluntary Bankruptcy. The commencement by the Company or any of its Subsidiaries of a voluntary case under the federal bankruptcy laws or any federal or state insolvency or similar laws or the consent by the Company or any of its Subsidiaries to the appointment of or taking possession by a receiver, liquidator, assignee, trustee, custodian or similar official for the Company or any of its Subsidiaries of any of the property of the Company or any of its Subsidiaries or the making by the Company or any of its Subsidiaries of an assignment for the benefit of creditors, or the failure by Company or any of its Subsidiaries generally to pay its debts as the debts become due.

4.7 Judgments, Awards. Any judgment or order for the payment of money is rendered against the Company or any of its Subsidiaries in an amount in excess of two hundred fifty thousand dollars ($250,000) individually or in the aggregate and either (i) enforcement proceedings are commenced by any creditor upon such judgment or order and not stayed, or (ii) there is any period of thirty (30) consecutive days during which such judgment has not been paid in full or a stay of enforcement of such judgment or order, by reason of a pending appeal or otherwise, is not in effect.

4.8 Attachment by Lenders. Any assets of the Company or any of its Subsidiaries shall be attached, levied upon, seized or repossessed, or come into the possession of a trustee, receiver or other custodian and a determination by any Holder, in good faith but in its sole discretion, that the same could have a material adverse effect on the prospect for the Holders to fully and punctually realize the full benefits conferred on the Holders by the Notes and/or the Note Purchase Agreement.

5. Remedies. Upon and after the occurrence of an Event of Default, the Holder shall be entitled to the exercise the rights and remedies set forth in the Note Purchase Agreement, this Note and under applicable law, all such rights and remedies being cumulative and enforceable alternatively, successively or concurrently. The Holder acknowledges and agrees that notwithstanding the terms and provisions of this Note, the Holder shall not be entitled to take any action permitted to be taken by the Holder under this Note unless the Holder holds, together with its Affiliates, Notes having an aggregate

10

principal amount equal to at least 40% of the aggregate principal amount of all of the Notes issued at the Initial Closing and the Holder gives prompt written notice to the other Holders after such exercise or exercises.

6. Assignment. Subject to the restrictions on transfer described in Section 9 below, the rights and obligations of the Company and Holder shall be binding upon and benefit the successors, assigns, heirs, administrators and transferees of the parties. The Company shall not be permitted to assign this Note without the prior written consent of the Holders.

7. Waiver of Notice. The Company hereby waives notice, presentment, demand, protest and notice of dishonor.

8. Transfer of This Note. With respect to any offer, sale or other disposition of this Note, the Holder will give written notice to the Company prior thereto, describing briefly the manner thereof, together with a written opinion of such Holder’s counsel, to the effect that such offer, sale or other distribution may be effected without registration or qualification (under any federal or state law then in effect); provided, that no opinion shall be required for any transfer to an Affiliate or if the transfer is made in compliance with the Securities Act, so long as the transferee can make the same representations and warranties at the time of transfer as set forth in Sections 4.5, 4.6, 4.7, 4.8, 4.9, 4.10 and 4.11 of the Note Purchase Agreement. Promptly upon delivering such written notice and opinion, if so required, the Holder may sell or otherwise dispose of this Note, all in accordance with the terms of the notice delivered to the Company. Each Note thus transferred shall bear a legend as to the applicable restrictions on transferability in order to ensure compliance with the Securities Act, unless in the opinion of counsel for the Company such legend is not required in order to ensure compliance with the Securities Act. The Company may issue stop transfer instructions to its transfer agent in connection with such restrictions. This Note is registered as to both principal and stated interest with the Company (or its agent) within the meaning of section 1.871-14(c)(1)(i) of the Income Tax Regulations. Accordingly, notwithstanding anything to the contrary in this paragraph, this Note, together with any interest thereon, may be transferred only (i) upon surrender of the Note by the transferor to the Company (or its agent) and the reissuance of the Note (or the issuance of a new Note) to the transferee, or (ii) by transfer of the right to principal and interest through a book-entry system meeting the requirements of section 1.871-14(c)(1)(i)(B) of the Income Tax Regulations that is maintained by the Company (or its agent). In the case of a Holder that is not a “United States person” within the meaning of section 7701(a)(30) of the Internal Revenue Code of 1986, as amended (the “Code”), so long as an exception under section 871(h) or section 881(c) of the Code does not apply, the Company (or its agent) shall not withhold any U.S. federal income tax with respect to such Holder provided that the Holder timely provides the Company (or its agent) with a statement that meets the requirements of section 871(h)(5) of the Code.

9. Treatment of Note. To the extent permitted by generally accepted accounting principles, the Company will treat, account and report the Note as debt and not equity for accounting purposes and with respect to any returns filed with federal, state or local tax authorities.

11

10. Notices. Any notice, request or other communication required or permitted hereunder shall be in writing and shall be deemed to have been duly given if personally delivered or if sent by nationally recognized courier service or mailed by registered or certified mail, postage prepaid, to the respective addresses of the parties as set forth on the signature pages hereto or if sent by facsimile to the respective facsimile numbers of the parties set forth on the signature pages hereto. Any party hereto may by notice so given change its address for future notice hereunder. Notice shall conclusively be deemed to have been given and received when personally delivered or three (3) business days after deposited in the mail or one business day after sent by courier or upon confirmation of facsimile delivery in the manner set forth above.

11. No Stockholder Rights. Nothing contained in this Note shall be construed as conferring upon Holder or any other Person the right to vote or to consent or to receive notice as a stockholder in respect of meetings of stockholders for the election of directors of the Company or any other matters or any rights whatsoever as a stockholder of the Company.

12. Governing Law. This Note shall be governed by and construed in accordance with the laws of the State of New York, excluding that body of law relating to conflict of laws.

13. Amendments and Waivers. No amendments or waivers of any provision of this Note, and no consent by the Holder to any departure by the Company, shall in any event be effective unless the same shall be in writing, and signed by the Holders of 66 2/3% of the outstanding principal amount of all of the Notes issued by the Company pursuant to the Note Purchase Agreement, and then such waiver or consent shall be effective only in the specific instance and for the purpose for which given. Any such amendment or waiver shall be binding upon all Notes and all holders thereof.

14. Severability. Any provision of this Note that is prohibited or unenforceable in a jurisdiction shall, as to such jurisdiction, be ineffective to the extent of such prohibition or unenforceability without invalidating the remaining provisions hereof, and any such prohibition or unenforceability in any jurisdiction shall not invalidate or render unenforceable such provision in any other jurisdiction.

15. WAIVER OF JURY TRIAL. EACH OF THE COMPANY AND THE HOLDER HEREBY (A) COVENANTS AND AGREES NOT TO ELECT A TRIAL BY JURY OF ANY ISSUE TRIABLE OF RIGHT BY A JURY, AND (B) WAIVES TRIAL BY JURY IN ANY ACTION OR PROCEEDING TO WHICH THE COMPANY AND THE HOLDER MAY BE PARTIES, ARISING OUT OF, IN CONNECTION WITH OR IN ANY WAY PERTAINING TO THIS NOTE AND THE NOTE PURCHASE AGREEMENT AND/OR ANY TRANSACTIONS, OCCURRENCES, COMMUNICATIONS, OR UNDERSTANDINGS (OR THE LACK OF ANY OF THE FOREGOING) RELATING IN ANY WAY TO DEBTOR-CREDITOR RELATIONSHIP

12

BETWEEN THE PARTIES. IT IS UNDERSTOOD AND AGREED THAT THIS WAIVER CONSTITUTES A WAIVER OF TRIAL BY JURY OF ALL CLAIMS AGAINST ALL PARTIES TO SUCH ACTIONS OR PROCEEDINGS, INCLUDING CLAIMS AGAINST PARTIES WHO ARE NOT PARTIES TO THIS NOTE. THIS WAIVER OF JURY TRIAL IS SEPARATELY GIVEN, KNOWINGLY, WILLINGLY AND VOLUNTARILY MADE BY THE COMPANY AND THE HOLDER, AND THE COMPANY AND THE HOLDER HEREBY AGREE THAT NO REPRESENTATIONS OF FACT OR OPINION HAVE BEEN MADE BY ANY INDIVIDUAL TO INDUCE THIS WAIVER OF TRIAL BY JURY OR TO IN ANY WAY MODIFY OR NULLIFY ITS EFFECT. THE COMPANY AND THE HOLDER ARE HEREBY AUTHORIZED TO SUBMIT THIS NOTE TO ANY COURT HAVING JURISDICTION OVER THE SUBJECT MATTER AND THE COMPANY AND THE HOLDER, SO AS TO SERVE AS CONCLUSIVE EVIDENCE OF SUCH WAIVER OF RIGHT TO TRIAL BY JURY. EACH OF THE COMPANY AND THE HOLDER REPRESENTS AND WARRANTS THAT IT HAS BEEN REPRESENTED IN THE SIGNING OF THIS NOTE AND IN THE MAKING OF THIS WAIVER BY INDEPENDENT LEGAL COUNSEL, SELECTED OF ITS OWN FREE WILL, AND/OR THAT IT HAS HAD THE OPPORTUNITY TO DISCUSS THIS WAIVER WITH COUNSEL.

16. Heading; References. All headings used herein are used for convenience only and shall not be used to construe or interpret this Note. Except as otherwise indicated, all references herein to Sections refer to Sections hereof.

[the remainder of this page intentionally left blank]

13

IN WITNESS WHEREOF, the Company has caused this Note to be issued this      day of December, 2004.

COMPANY:
	CRITICAL PATH, INC., a California corporation
	By:
		Name:
		Title:
	Critical Path, Inc. 350 The Embarcadero San Francisco, CA 94105-1204 Telecopy: (415) 541-2300 Attention: Chief Financial Officer
	With a copy to:
	Paul, Hastings, Janofsky & Walker, LLP 55 Second Street, 24th Floor San Francisco, California 94105-3441 Telecopy: (415) 856-7100 Attention: Gregg Vignos, Esq.

Name of Holder:

Address:

Telephone:

Facsimile:

EX-4.2

Exhibit 4.2

THIS WARRANT AND ANY SECURITIES ACQUIRED UPON THE EXERCISE OF THIS WARRANT HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE OF THE UNITED STATES OR FOREIGN JURISDICTION. NEITHER THIS WARRANT, SUCH SECURITIES NOR ANY INTEREST THEREIN MAY BE TRANSFERRED EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER SUCH ACT AND APPLICABLE STATE AND FOREIGN SECURITIES LAWS OR PURSUANT TO AN APPLICABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT AND SUCH LAWS.

CRITICAL PATH, INC.

SERIES F REDEEMABLE CONVERTIBLE PREFERRED

STOCK PURCHASE WARRANT

This certifies that, for good and valuable consideration, Critical Path, Inc., a California corporation (the “Company”), grants to                                                      , a Delaware limited liability company (the “Warrantholder”), the right to subscribe for and purchase from the Company, during the Exercise Period (as hereinafter defined),                      validly issued, fully paid and nonassessable shares, par value $0.001, of Series F Redeemable Convertible Preferred Stock of the Company (the “Warrant Shares”), at the exercise price of $1.40 per share (the “Exercise Price”), all subject to the terms, conditions and adjustments herein set forth. Capitalized terms used herein shall have the meanings ascribed to such terms in Section 9 below.

1. Warrant. This Warrant is issued pursuant to, and in accordance with, the Note and Warrant Purchase Agreement and is subject to the applicable terms thereof.

2. Exercise of Warrant; Payment of Taxes.

2.1 Exercise of Warrant. Subject to the terms and conditions set forth herein, this Warrant may be exercised at any time, in whole or in part, by the Warrantholder during the Exercise Period by:

(a) the surrender of this Warrant to the Company, with a duly executed Exercise Form, and

(b) at the option of the Warrantholder, any of (i) the delivery of payment to the Company, for the account of the Company, by cash, wire transfer, certified or official bank check or any other means approved by the Company, of the aggregate Exercise Price in lawful money of the United States of America, (ii) the exercise of the Conversion Right as provided in Section 2.2 below or (iii) the tendering to the Company of Notes having an aggregate unpaid principal and interest amount equal to the aggregate Exercise Price (the foregoing clause (iii), the “Tender Exercise”).

The Company agrees that the Warrant Shares shall be deemed to be issued to the Warrantholder as the record holder of such Warrant Shares as of the close of business on the date on which this Warrant shall have been surrendered and payment made for the Warrant Shares as aforesaid. The Company agrees that if the Warrantholder elects the Tender Exercise and delivers this Note in connection with such Tender Exercise having an aggregate unpaid principal and interest amount that is greater than the aggregate Exercise Price, then, the Company shall promptly (but in any event not later than five days) after such Tender Exercise, issue to the Warrantholder new Notes identical to the Notes having an aggregate principal amount equal to the excess of (i) the aggregate and unpaid principal and interest amount of the Notes delivered to the Company in connection with the Tender Exercise minus (ii) the portion of the aggregate unpaid principal and interest amount of such Notes that was used in the Tender Exercise to pay the aggregate Exercise Price.

If during the Exercise Period (i) the Warrantholder exercises this Warrant or any of the events described in Section 5.7 occur and (ii) prior to the receipt of the Warrant Shares, the shares of Common Stock issuable upon conversion of the Warrant Shares and/or any of the consideration described in Section 5.7(a) or Section 5.7(b) the Warrantholder is required to obtain a consent or waiver under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended, then the Exercise Period of this Warrant shall be extended to the extent necessary to enable the Warrantholder to obtain such consent or waiver and the Company shall reserve and set aside such Warrant Shares, shares of Common Stock and consideration, as the case may be, for the benefit of the Warrantholder for delivery to the Warrantholder after such consent or waiver is obtained.

2.2 Conversion Right.

(a) In lieu of the payment of the aggregate Exercise Price, the Warrantholder shall have the right (but not the obligation), to require the Company to convert this Warrant, in whole or in part, into shares of Series F Preferred Stock (the “Conversion Right”) as provided for in this Section 2.2. Upon exercise of the Conversion Right, the Company shall deliver to the Warrantholder (without payment by the Warrantholder of any of the Exercise Price) in accordance with Section 2.1(b) that number of whole shares of Series F Preferred Stock equal to the quotient (rounded down to the nearest whole share) obtained by dividing (i) the value of the Warrant or portion thereof at the time the Conversion Right is exercised (determined by subtracting the aggregate Exercise Price at the time of the exercise of the Conversion Right from the aggregate Current Market Price for the shares of Series F Preferred Stock issuable upon exercise of the Warrant at the time of the exercise of the Conversion Right) by (ii) the Current Market Price of one share of Series F Preferred Stock at the time of the exercise of the Conversion Right.

(b) The Conversion Right may be exercised by the Warrantholder on any Business Day prior to the end of the Exercise Period by surrender of this Warrant to the Company, with a duly executed Exercise Form with the conversion section completed, exercising the Conversion Right and specifying the total number of shares of Series F Preferred Stock that the Warrantholder will be issued pursuant to such conversion.

- 2 -

(c) No fractional shares of Series F Preferred Stock shall be issued upon exercise of this Warrant. If such exercise would result in the issuance of any fractional shares, then the Company shall, in lieu of issuing any such fractional share, pay cash equal to the product of such fraction multiplied by the Current Market Price of one share of Series F Preferred Stock on the date of exercise.

2.3 Warrant Shares Certificate. A stock certificate or certificates for the Warrant Shares specified in the Exercise Form shall be delivered to the Warrantholder within ten (10) Business Days after receipt of the Exercise Form by the Company and, if the Conversion Right is not exercised, the payment by the Warrantholder of the aggregate Exercise Price. If this Warrant shall have been exercised only in part, the Company shall, at the time of delivery of the stock certificate or certificates, deliver to the Warrantholder a new Warrant evidencing the right to purchase the remaining Warrant Shares, which new Warrant shall in all other respects be identical to this Warrant.

2.4 Payment of Taxes. The Company will pay all documentary stamp or other issuance taxes, if any, attributable to the issuance of Warrant Shares upon the exercise of this Warrant; provided, however, that the Company shall not be required to pay any tax or taxes which may be payable in respect of any transfer involved in the issue or delivery of any Warrants or Warrant certificates or Warrant Shares in a name other than that of the then Warrantholder as reflected upon the books of the Company.

3. Restrictive Legends. Except as otherwise permitted by this Section 3, (a) each Warrant (and each Warrant issued in substitution for any Warrant pursuant to Section 6) shall be stamped or otherwise imprinted with a legend in substantially the form as set forth on the cover of this Warrant and (b) each certificate for Warrant Shares issued upon the exercise of any Warrant and each certificate issued upon the direct or indirect transfer of any such Warrant Shares shall be stamped or otherwise imprinted with the following legend:

THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”) OR THE SECURITIES LAWS OF ANY STATE OF THE UNITED STATES OR ANY FOREIGN JURISDICTION. THE SECURITIES MAY NOT BE TRANSFERRED EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER SUCH ACT AND APPLICABLE STATE AND FOREIGN SECURITIES LAWS OR PURSUANT TO AN APPLICABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT AND SUCH LAWS.

Notwithstanding the foregoing, the Warrantholder may require the Company to issue a Warrant or a certificate for Warrant Shares, in each case without a legend, if either

(i) such Warrant or such Warrant Shares, as the case may be, have been registered for resale under the Securities Act, (ii) the Warrantholder has delivered to the Company an opinion of legal counsel (from a firm reasonably satisfactory to the Company) which opinion shall be addressed to the Company and be reasonably satisfactory in form and

- 3 -

substance to the Company’s counsel, to the effect that such registration is not required with respect to such Warrant or such Warrant Shares, as the case may be or (iii) such Warrant or Warrant Shares may be sold pursuant to Rule 144 (or any successor provision then in effect) under the Securities Act.

4. Reservation and Registration of Shares. The Company covenants and agrees as follows:

(a) All Warrant Shares that are issued upon the exercise of this Warrant and all shares of Common Stock that are issued upon the conversion of the Warrant Shares shall, upon issuance, be validly issued, fully paid and non-assessable, and not subject to any preemptive rights, and be free from all taxes, liens, security interests, charges, and other encumbrances with respect to the issuance thereof, other than taxes in respect of any transfer occurring contemporaneously with such issue.

(b) The Company shall at all times have authorized and reserved, and shall keep available and free from preemptive rights, a sufficient number of shares of Series F Preferred Stock to provide for the exercise of the rights represented by this Warrant and a sufficient number of shares of Common Stock to provide for the conversion of the Warrant Shares.

(c) The Company shall not, by amendment of its Articles of Incorporation or through any reorganization, transfer of assets, spin-off, consolidation, merger, dissolution, issue or sale of securities or any other action or inaction, seek to avoid the observance or performance of any of the terms of this Warrant, and shall at all times in good faith assist in performing and giving effect to the terms hereof and in the taking of all such actions as may be necessary or appropriate in order to protect the rights of the Warrantholder against dilution or other impairment.

5. Anti-dilution Adjustments. The Exercise Price and the number of Warrant Shares to be received upon exercise of this Warrant shall be subject to adjustment as follows:

5.1 Dividend, Subdivision, Combination or Reclassification of Series F Preferred Stock. Notwithstanding that no shares of Series F Preferred Stock may be outstanding, in the event that the Company shall at any time or from time to time, after the issuance of this Warrant but prior to the exercise hereof, (v) make a dividend or distribution on the outstanding shares of Series F Preferred Stock payable in Capital Stock, (w) subdivide the outstanding shares of Series F Preferred Stock into a larger number of shares, (x) combine the outstanding shares of Series F Preferred Stock into a smaller number of shares, (y) issue any shares of its Capital Stock in a reclassification of the Series F Preferred Stock or (z) take any of the actions described in the foregoing clauses (v)-(y) with respect to its shares of Common Stock for which an adjustment is not made pursuant to the anti-dilution provisions set forth in Sections 7(c) and 7(f) of the Series F Certificate of Determination (other than any such event for which an adjustment is made pursuant to another clause of this Section 5), then, and in each such case, (A) the aggregate number of Warrant Shares for which this Warrant is exercisable (the “Warrant Share Number”) immediately prior to such event shall be adjusted (and any other appropriate actions shall be taken by the Company) so that the Warrantholder shall be entitled to receive upon exercise of

- 4 -

this Warrant the number of shares of Series F Preferred Stock and other securities of the Company that it would have owned or would have been entitled to receive upon or by reason of any of the events described above, had this Warrant been exercised immediately prior to the occurrence of such event and had the shares of Series F Preferred Stock been converted to shares of Common Stock immediately prior to the occurrence of such event and (B) the Exercise Price payable upon the exercise of this Warrant shall be adjusted by multiplying such Exercise Price immediately prior to such adjustment by a fraction, the numerator of which shall be the number of Warrant Shares issuable upon the exercise of this Warrant immediately prior to such adjustment, and the denominator of which shall be the number of Warrant Shares issuable immediately thereafter. An adjustment made pursuant to this Section 5.1 shall become effective retroactively (x) in the case of any such dividend or distribution, to a date immediately following the close of business on the record date for the determination of holders of shares of Series F Preferred Stock entitled to receive such dividend or distribution or (y) in the case of any such subdivision, combination or reclassification, to the close of business on the day upon which such corporate action becomes effective.

5.2 Certain Distributions. Notwithstanding that no shares of Series F Preferred Stock may be outstanding, in case the Company shall at any time or from time to time, after the issuance of this Warrant but prior to the exercise hereof, distribute to all holders of shares of Series F Preferred Stock or all holders of shares of Common Stock (including any such distribution made in connection with a merger or consolidation in which the Company is the resulting or surviving Person and shares of Series F Preferred Stock and shares of Common Stock are not changed or exchanged) cash, evidences of indebtedness of the Company or another issuer, securities of the Company or another issuer or other assets (excluding dividends or distributions payable in shares of Series F Preferred Stock for which adjustment is made under Section 5.1 and any distribution in connection with an Excluded Transaction) or rights or warrants to subscribe for or purchase any of the foregoing, then, and in each such case, (A) the Exercise Price then in effect shall be adjusted (and any other appropriate actions shall be taken by the Company) by being multiplied by a fraction (i) the numerator of which shall be such Current Market Price of Series F Preferred Stock immediately prior to the date of distribution less the then fair market value (as determined by the Board of Directors in the exercise of their fiduciary duties) of the portion of the cash, evidences of indebtedness, securities or other assets so distributed or of such rights or warrants applicable to one share of Series F Preferred Stock and (ii) the denominator of which shall be the Current Market Price of the Series F Preferred Stock immediately prior to the date of distribution (but such fraction shall not be greater than one) and (B) the Warrant Share Number shall be increased by being multiplied by a fraction (i) the numerator of which shall be the Current Market Price of one share of Series F Preferred Stock immediately prior to the record date for the distribution of such cash, evidences of indebtedness, securities, other assets or rights or warrants and (ii) the denominator of which shall be the Current Market Price of one share of Series F Preferred Stock immediately prior to such record date less the fair market value (as determined by the Board of Directors in the exercise of their fiduciary duties) of the portion of such cash, evidences of indebtedness, securities, other assets or rights or warrants so distributed. Such adjustment shall be made whenever any such distribution is made and shall become effective retroactively to a date immediately following the close of business on the record date for the determination of stockholders entitled to receive such distribution.

- 5 -

5.3 Other Changes. In case the Company at any time or from time to time, after the issuance of this Warrant but prior to the exercise hereof, shall take any action affecting its Series F Preferred Stock or its Common Stock similar to or having an effect similar to any of the actions described in any of Sections 5.1, 5.2, or 5.7 (but not including any action described in any such Section) and the Board of Directors in good faith determines that it would be equitable in the circumstances to adjust the Exercise Price and Warrant Share Number as a result of such action, then, and in each such case, the Exercise Price and Warrant Share Number shall be adjusted in such manner and at such time as the Board of Directors in good faith determines would be equitable in the circumstances (such determination to be evidenced in a resolution, a certified copy of which shall be mailed to the Warrantholder).

5.4 No Adjustment; Par Value Minimum. Notwithstanding anything herein to the contrary, no adjustment under this Section 5 need be made to the Exercise Price or Warrant Share Number if the Company receives written notice from the Warrantholder that no such adjustment is required. Notwithstanding any other provision of this Warrant, the Exercise Price shall not be adjusted below the par value of a share of Series F Preferred Stock.

5.5 Abandonment. If the Company shall take a record of the holders of shares of its Series F Preferred Stock or its Common Stock for the purpose of entitling them to receive a dividend or other distribution, and shall thereafter and before the distribution to stockholders thereof legally abandon its plan to pay or deliver such dividend or distribution, then no adjustment in the Exercise Price or Warrant Share Number shall be required by reason of the taking of such record.

5.6 Certificate as to Adjustments. Upon any adjustment in the Exercise Price or Warrant Share Number, the Company shall within a reasonable period (not to exceed ten (10) days) following any of the foregoing transactions deliver to the Warrantholder a certificate, signed by (i) the Chief Executive Officer of the Company and (ii) the Chief Financial Officer of the Company, setting forth in reasonable detail the event requiring the adjustment and the method by which such adjustment was calculated and specifying the Exercise Price and Warrant Share Number in effect following such adjustment.

5.7 Spin-off; Reorganization, Reclassification or Change of Control.

(a) In case of any spin-off by the Company of another Person (the “Spin-off Entity”) at any time after the issuance of this Warrant but prior to the exercise hereof, the Company shall issue to the Warrantholder a new warrant, in form and substance satisfactory to the Company and the Majority Warrantholders, entitling the Warrantholder to purchase, at the exercise price equal to the excess of the Exercise Price in effect immediately prior to such spin-off over the adjusted Exercise Price pursuant to Section 5.2, the number of shares of preferred stock or other proprietary interest in the Spin-off Entity that the Warrantholder would have owned had the Warrantholder, immediately prior to such spin-off, exercised this Warrant.

(b) In case of any capital reorganization, reclassification, Change of Control, merger or consolidation (other than a “reincorporation” merger or consolidation of the Company in which the Company is the surviving corporation) of the Company or other change of outstanding shares of Series F Preferred Stock (other than a change in par value, or from par

- 6 -

value to no par value, or from no par value to par value) (each, a “Transaction”) at any time after the issuance of this Warrant but prior to the exercise hereof, the Company shall execute and deliver to the Warrantholder at least ten (10) Business Days prior to effecting such Transaction a certificate stating that the Warrantholder shall have the right thereafter to exercise this Warrant for, or exchange this Warrant for a new Warrant exercisable for, the kind and amount of shares of stock or other securities, property or cash receivable upon such Transaction by a holder of the number of shares of Series F Preferred Stock into which this Warrant could have been exercised immediately prior to such Transaction, and provision shall be made therefor in the agreement, if any, relating to such Transaction. Such certificate shall provide for adjustments which shall be as nearly equivalent as may be practicable to the adjustments provided for in this Section 5. The provisions of this Section 5.7 and any equivalent thereof in any such certificate similarly shall apply to successive transactions.

5.8 Notices. In case at any time or from time to time:

(a) the Company shall declare a dividend (or any other distribution) on its shares of Series F Preferred Stock or its shares of Common Stock;

(b) the Company shall authorize the granting to the holders of shares of its Series F Preferred Stock or its shares of Common Stock rights or warrants to subscribe for or purchase any shares of Capital Stock or any other rights or warrants;

(c) there shall occur a spin-off or Transaction; or

(d) the Company shall take any other action that would require a vote of the Company’s stockholders;

then the Company shall mail to the Warrantholder, as promptly as possible but in any event at least ten (10) Business Days prior to the applicable date hereinafter specified, a notice stating (A) the date on which a record is to be taken for the purpose of such dividend, distribution or granting of rights or warrants or, if a record is not to be taken, the date as of which the holders of Series F Preferred Stock of record and the holders of Common Stock of record to be entitled to such dividend, distribution or granting of rights or warrants are to be determined, or (B) the date on which such spin-off or Transaction is expected to become effective and the date as of which it is expected that holders of Series F Preferred Stock of record and the holders of Common Stock of record shall be entitled to exchange their Series F Preferred Stock or Common Stock, as the case may be, for shares of stock or other securities or property or cash deliverable upon such spin-off or Transaction. Notwithstanding the foregoing, in the case of any event to which Section 5.7 is applicable, the Company shall also deliver the certificate described in such Section 5.7 to the Warrantholder at least ten (10) Business Days prior to effecting such reorganization or reclassification as aforesaid.

6. Loss or Destruction of Warrant. Subject to the terms and conditions hereof, upon receipt by the Company of evidence reasonably satisfactory to it of the loss, theft, destruction or mutilation of this Warrant and, in the case of loss, theft or destruction, of such bond or indemnification as the Company may reasonably require, and, in the case of such mutilation, upon surrender and cancellation of this Warrant, the Company will execute and deliver a new Warrant of like tenor.

- 7 -

7. Ownership of Warrant. The Company may deem and treat the person in whose name this Warrant is registered as the holder and owner hereof (notwithstanding any notations of ownership or writing hereon made by anyone other than the Company) for all purposes and shall not be affected by any notice to the contrary, until presentation of this Warrant for registration of transfer.

8. Amendments. No amendments or waivers of any provision of this Warrant, and no consent by the Warrantholder to any departure by the Company, shall in any event be effective unless the same shall be in writing, and signed by Warrantholders holding Warrants exercisable for shares of Series F Preferred Stock representing at least 66 2/3% of the shares of Series F Preferred Stock issuable upon exercise of all of the Warrants then outstanding, and then such waiver or consent shall be effective only in the specific instance and for the purpose for which given. Any such amendment or waiver shall be binding upon all Warrantholders and all holders thereof.

9. Series F Preferred Stock. The Company shall not propose, make, effect or approve any amendment or restatement of its Articles of Incorporation or By-Laws which adversely affects or harms the Series F Preferred Stock (notwithstanding that no Series F Preferred Stock may then be outstanding), whether by merger, consolidation, business combination or otherwise.

10. Definitions. As used herein, unless the context otherwise requires, the following terms have the following respective meanings:

“Board of Directors” means the Board of Directors of the Company.

“Business Day” means any day other than a Saturday, Sunday or other day on which commercial banks in the State of New York or the State of California are authorized or required by law or executive order to close.

“Capital Stock” means, with respect to any Person, any and all shares, interests, participations, rights in, or other equivalents (however designated and whether voting or non-voting) of such Person’s capital stock and any and all rights, warrants or options exchangeable for or convertible into such capital stock (but excluding any debt security whether or not it is exchangeable for or convertible into such capital stock).

“Change of Control” means (i) any merger, consolidation or other business combination transaction (or series of related transactions) in which the stockholders owning a majority of the voting securities of the Company prior to such transaction do not own a majority of the voting securities of the surviving entity, (ii) any tender offer, exchange offer or other transaction whereby any person or “group” obtains a majority of the outstanding shares of capital stock entitled to vote in the election of the Board of Directors, (iii) any proxy contest in which a majority of the Board of Directors (or persons appointed by such Board of Directors) prior to such contest do not constitute a majority of the Board of Directors after such contest, (iv) a sale of all or substantially all of the assets of the Company or (v) any other transaction described in any stockholder rights agreement or “poison pill”, if any, to which the Company is a party,

- 8 -

which permits the holders of any rights or similar certificates to exercise the rights evidenced thereby and would require the Board of Directors to waive the application of such stockholder rights agreement or “poison pill” unless the Board of Directors has determined in good faith that such Person has inadvertently triggered such right.

“Common Stock” means the Common Stock, par value $0.001 per share, of the Company.

“Common Stock Equivalent” means any security or obligation which is by its terms convertible into or exercisable into shares of Common Stock, including, without limitation, any option, warrant or other subscription or purchase right with respect to Common Stock.

“Company” has the meaning set forth in the first paragraph of this Warrant.

“Conversion Right” has the meaning set forth in Section 2.2(a) of this Warrant.

“Current Market Price” means, as of the date of determination, (a) the average of the daily Market Price under clause (a), (b) or (c) of the definition thereof of the Series F Preferred Stock during the immediately preceding thirty (30) trading days ending on such date, and (b) if the Common Stock is not then listed or admitted to trading on any national securities exchange or quoted in the over-the-counter market, then the Market Price under clause (d) of the definition thereof on such date.

“Excluded Transaction” means (a) any issuance of shares of stock or options to purchase shares of Common Stock (subject to adjustment in the event of stock splits, combinations or similar occurrences) to employees, officers, directors or consultants of the Company pursuant to a stock option plan or other employee benefit arrangement approved by the Board of Directors, (b) any issuance of Common Stock upon the conversion of Series F Preferred Stock, (ii) as a dividend on shares of Series F Preferred Stock or (iii) upon conversion or exercise of any Common Stock Equivalents, (c) any issuance of Warrant Shares, (d) any issuance of capital stock of the Company issued in consideration of an acquisition, approved by the Board of Directors, by the Company of another Person and (e) any issuance of shares of Common Stock and Common Stock Equivalents in strategic transactions (which may not be private equity or venture capital financing transactions) approved by the Board of Directors to Persons that are not principally engaged in financial investing.

“Exercise Form” means an Exercise Form in the form annexed hereto as Exhibit A.

“Exercise Period” means the period beginning on December 30, 2004 and terminating on the Series F Automatic Redemption Date (as defined in the Series F Certificate of Determination).

“Exercise Price” has the meaning set forth in the first paragraph of this Warrant.

“Market Price” means, as of the date of determination, the greater of (a) (i) if the Common Stock is listed on a national securities exchange, the closing price per share of Common Stock on such date published in The Wall Street Journal (National Edition) or, if no

- 9 -

such closing price on such date is published in The Wall Street Journal (National Edition), the average of the closing bid and asked prices on such date, as officially reported on the principal national securities exchange on which the Common Stock is then listed or admitted to trading; or (ii) if the Common Stock is not then listed or admitted to trading on any national securities exchange but is designated as a National Market System security by Nasdaq, the last trading price of the Common Stock on such date; or (iii) if there shall have been no trading on such date or if the Common Stock is not designated as a National Market System security by Nasdaq, the average of the reported closing bid and asked prices of the Common Stock on such date as shown by Nasdaq and reported by any member firm of the New York Stock Exchange selected by the Company; or (iv) if none of (i), (ii) or (iii) is applicable, a market price per share determined mutually by the Board of Directors and the Majority Warrantholders or, if the Board of Directors and the Majority Warrantholders shall fail to agree, at the Company’s expense by an appraiser chosen by the Board of Directors and reasonably acceptable to the Majority Warrantholders and (b) the sum of the Series F Accreted Value (as defined in the Series F Certificate of Determination), plus all dividends accrued since the previous Series F Accrual Date (as defined in the Series F Certificate of Determination). Any determination of the Market Price by an appraiser shall be based on a valuation of the Company as an entirety without regard to any discount for minority interests or disparate voting rights among classes of capital stock.

“Majority Warrantholders” means the holders of a majority of Warrant Shares issuable upon exercise of all of the warrants issued pursuant to the Note and Warrant Purchase Agreement assuming the exercise of all such warrants.

“Nasdaq” means The Nasdaq Stock Market, Inc.

“Note and Warrant Agreement” means the Note and Warrant Purchase Agreement, dated December 29, 2004, among the Company and the parties listed therein.

“Notes” has the meaning set forth in the Note and Warrant Purchase Agreement.

“Person” means any individual, firm, corporation, partnership, limited liability company, trust, incorporated or unincorporated association, joint venture, joint stock company, governmental body or other entity of any kind.

“Securities Act” means the Securities Act of 1933, as amended, and the rules and regulations of the Securities and Exchange Commission thereunder.

“Series F Certificate of Determination” means the Certificate of Determination of Preferences of the Series F Preferred Stock.

“Series F Preferred Stock” means the Series F Cumulative Redeemable Convertible Participating Preferred Stock, par value $0.001 per share, of the Company.

“Spin-off Entity” has the meaning set forth in Section 5.7 of this Warrant.

“Transaction” has the meaning set forth in Section 5.8 of this Warrant.

“Warrant Share Number” has the meaning set forth in Section 5.1 of this Warrant.

- 10 -

“Warrant Shares” has the meaning set forth in the first paragraph of this Warrant.

“Warrantholder” has the meaning set forth in the first paragraph of this Warrant.

11. Miscellaneous.

11.1 Entire Agreement. This Warrant and the Note and Warrant Purchase Agreement constitute the entire agreement between the Company and the Warrantholder with respect to this Warrant and supersede all prior agreements and understanding with respects to the subject matter of this Warrant.

11.2 Binding Effect; Benefits. This Warrant shall inure to the benefit of and shall be binding upon the Company and the Warrantholder and their respective permitted successors and assigns. Nothing in this Warrant, expressed or implied, is intended to or shall confer on any person other than the Company and the Warrantholder, or their respective permitted successors or assigns, any rights, remedies, obligations or liabilities under or by reason of this Warrant.

11.3 Headings. The headings in this Warrant are for convenience of reference only and shall not limit or otherwise affect the meaning of this Warrant.

11.4 Notices. All notices, demands and other communications provided for or permitted hereunder shall be made in writing and shall be by registered or certified first-class mail, return receipt requested, facsimile, courier service or personal delivery:

(a) if to the Company:

Critical Path, Inc.

350 The Embarcadero

San Francisco, CA 94105

Facsimile:

Attention:

with a copy to:

Paul, Hastings, Janofsky & Walker LLP

55 Second Street, 24th Floor

San Francisco, CA 94105-3441

Facsimile: (415) 856-7100

Attention:

(b) if to the Warrantholder:

c/o General Atlantic Service Corporation

3 Pickwick Plaza

Greenwich, CT 06830

Telecopy: (203) 622-8818

Attention: Matthew Nimetz

- 11 -

[Campina:

c/o 7th Cheung Kong Center

2 Queen’s Road Central

Hong Kong

Attention: Edmond IP]

[Richmond III:

10563 Brunswick Road, Suite 7

Grass Valley, CA 95945]

with a copy to:

Paul, Weiss, Rifkind, Wharton & Garrison LLP

1285 Avenue of the Americas

New York, NY 10019-6064

Telecopy: (212 757-3990)

Attention: Douglas A. Cifu, Esq.

All such notices, demands and other communications shall be deemed to have been duly given when delivered by hand, if personally delivered; when delivered by courier, if delivered by commercial courier service; five (5) Business Days after being deposited in the mail, postage prepaid, if mailed; and when receipt is mechanically acknowledged, if faxed. Any party may by notice given in accordance with this Section 10.4 designate another address or Person for receipt of notices hereunder.

11.5 Severability. Any term or provision of this Warrant which is invalid or unenforceable in any jurisdiction shall, as to such jurisdiction, be ineffective to the extent of such invalidity or unenforceability without rendering invalid or unenforceable the terms and provisions of this Warrant or affecting the validity or enforceability of any of the terms or provisions of this Warrant in any other jurisdiction.

11.6 GOVERNING LAW. THIS WARRANT SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK WITHOUT REGARD TO THE CONFLICTS OF LAW PRINCIPLES THEREOF.

11.7 No Rights or Liabilities as Stockholder. Nothing contained in this Warrant shall be determined as conferring upon the Warrantholder any rights as a stockholder of the Company or as imposing any liabilities on the Warrantholder to purchase any securities, whether such liabilities are asserted by the Company or by creditors or stockholders of the Company or otherwise.

[Remainder of this page intentionally left blank]

- 12 -

IN WITNESS WHEREOF, the Company has caused this Warrant to be signed by its duly authorized officer.

CRITICAL PATH, INC.

By:

Name:

Title:

Dated: December 30, 2004

- 13 -

Exhibit A

EXERCISE FORM *

(To be executed upon exercise of this Warrant)

The undersigned hereby irrevocably elects to exercise the right, represented by this Warrant, to purchase              shares of Series F Preferred Stock and [herewith tenders payment for such shares to the order of the Company in the amount of $                    ] [hereby exercises its Conversion Right] in accordance with the terms of this Warrant. The undersigned requests that a certificate for such [Warrant Shares] [that number of Warrant Shares to which the undersigned is entitled as calculated pursuant to Section 2.2] be registered in the name of the undersigned and that such certificates be delivered to the undersigned’s address below.

The undersigned represents that it is acquiring such shares for its own account for investment and not with a view to or for sale in connection with any distribution thereof (subject, however, to any requirement of law that the disposition thereof shall at all times be within its control).

Dated:                     , 200  

Signature
	(Print Name and Title)
	(Street Address)
	(City)            (State)             (Zip Code)

* The Investors may have a reporting obligation under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended, upon exercise of the Warrants and acquiring the Warrant Shares and should consult counsel prior to exercising the Warrant.

EX-4.9

Exhibit 4.9

AMENDMENT NO. 6

TO

PREFERRED STOCK RIGHTS AGREEMENT

This Amendment No. 6 to Preferred Stock Rights Agreement (this “Amendment”) is dated as of December 29, 2004, between Critical Path, Inc. (the “Company”), and Computershare Trust Company, Inc. (the “Rights Agent”), with reference to the following:

A. The Company and the Rights Agent entered into that certain Preferred Stock Rights Agreement, dated as of March 19, 2001, as amended by that certain Amendment No. 1 to Preferred Stock Rights Agreement, dated as of November 6, 2001, that certain Amendment No. 2 to Preferred Stock Rights Agreement, dated as of November 18, 2003, that certain Amendment No. 3 to Preferred Stock Rights Agreement, dated as of January 16, 2004, that certain Amendment No. 4 to Preferred Stock Rights Agreement, dated as of March 9, 2004 and that certain Amendment No. 5 to Preferred Stock Rights Agreement dated as of June 24, 2004 (the “Agreement”).

B. The Company desires to amend the Agreement in certain respects in order to permit certain investors to purchase securities being offered by the Company without causing such investors to become Acquiring Persons (as defined in the Agreement) and thereby trigger the occurrence of a Distribution Date (as defined in the Agreement).

C. Under the Agreement, the Company and the Rights Agent may amend the Agreement, at any time prior to a Distribution Date, which has yet to occur.

NOW, THEREFORE, pursuant to Section 27 of the Agreement, the Company and the Rights Agent hereby amend, effective upon the date hereof, the definition of the term “Acquiring Person” set forth in Section 1(a) of the Agreement to read in its entirety as follows:

“(a) “ACQUIRING PERSON” shall mean any Person who or which, together with all Affiliates and Associates of such Person, shall be the Beneficial Owner of 15% or more of the Common Shares of the Company then outstanding, but shall not include the Company, any Subsidiary of the Company or any employee benefit plan of the Company or of any Subsidiary of the Company, or any entity holding Common Shares for or pursuant to the terms of any such plan. Notwithstanding the foregoing, no Person shall be deemed to be an Acquiring Person as the result of an acquisition of Common Shares or Exchangeable Shares by the Company which, by reducing the number of shares outstanding, increases the proportionate number of shares beneficially owned by such Person to 15% or more of the Common Shares of the Company then outstanding; provided, however, that if a Person shall become the Beneficial Owner of 15% or more of the Common Shares of the Company then outstanding by reason of share repurchases by the Company and shall, after such share repurchases by the Company, become the Beneficial Owner of any additional Common Shares of the Company (other than pursuant to a dividend or distribution paid or made by (i) the Company on the outstanding Common Shares in Common Shares or pursuant to a split or subdivision of the outstanding Common Shares or (ii) Exchangeco on the outstanding Exchangeable Shares in Exchangeable Shares or pursuant to a split or subdivision of the outstanding Exchangeable Shares), then such Person shall be deemed to be an Acquiring Person unless, upon becoming the Beneficial Owner of such additional

Common Shares of the Company, such Person does not beneficially own 15% or more of the Common Shares of the Company then outstanding. Notwithstanding the foregoing:

(i) if the Company’s Board of Directors determines in good faith that a Person who would otherwise be an “Acquiring Person,” as defined pursuant to the provisions of this Section 1(a), has become such inadvertently (including, without limitation, because (x) such Person was unaware that such Person Beneficially Owned a percentage of the Common Shares of the Company that would otherwise cause such Person to be an “Acquiring Person,” as defined pursuant to the provisions of this Section 1(a), or (y) such Person was aware of the extent of the Common Shares of the Company such Person Beneficially Owned but had no actual knowledge of the consequences of such Beneficial Ownership under this Agreement) and without any intention of changing or influencing control of the Company, and if such Person divested or divests as promptly as practicable a sufficient number of Common Shares so that such Person would no longer be an “Acquiring Person,” as defined pursuant to the provisions of this Section 1(a), then such Person shall not be deemed to be or to have become an “Acquiring Person” for any purposes of this Agreement;

(ii) if, as of the date of this Agreement, any Person is the Beneficial Owner of 15% or more of the Common Shares of the Company outstanding, such Person shall not be or become an “Acquiring Person,” as defined pursuant to the provisions of this Section 1(a), unless and until such time as such Person shall become the Beneficial Owner of additional Common Shares of the Company (other than pursuant to a dividend or distribution paid or made by (x) the Company on the outstanding Common Shares in Common Shares or pursuant to a split or subdivision of the outstanding Common Shares or (y) Exchangeco on the outstanding Exchangeable Shares in Exchangeable Shares or pursuant to a split or subdivision of the outstanding Exchangeable Shares), unless, upon becoming the Beneficial Owner of such additional Common Shares of the Company, such Person is not then the Beneficial Owner of 15% or more of the Common Shares of the Company then outstanding; and

(iii) the term “Acquiring Person” shall not mean:

A. General Atlantic Partners 74, L.P., a Delaware limited partnership, GAP Coinvestment Partners II, L.P., a Delaware limited partnership, GapStar, LLC, a Delaware limited liability company and GAPCO GmbH & Co. KG, a German limited partnership (referred to collectively with their respective Affiliates and Associates as “GAP”) so long as GAP does not increase (other than an increase resulting solely from a reduction of the number of shares of outstanding Common Stock, including by reason of repurchases of Common Stock or Exchangeable Shares by the Company, or a dividend or distribution paid or made by the Company or Exchangeco on, or a split or subdivision of, any shares of their respective capital stock) its Beneficial Ownership of

2

Common Stock to a percentage of the outstanding shares of Common Stock at any time that is greater than: (1) the percentage of the outstanding shares of Common Stock represented by the sum of (x) the shares as to which GAP has Beneficial Ownership as of the close of business on December 29, 2004, assuming, for purposes of this calculation, all warrants and other securities convertible into or exercisable for Common Stock, or any other rights to purchase Common Stock, in all cases where held or enjoyed by GAP, are immediately convertible or exercisable, plus (y) the shares as to which GAP obtains (or is entitled to obtain) Beneficial Ownership directly from the Company pursuant to the consummation of the transactions described in that certain Note and Warrant Purchase Agreement (the “December Purchase Agreement”), dated December 29, 2004, by and among the Company and the “Investors” party thereto, including; or (2) such lesser percentage as to which GAP has Beneficial Ownership following any transfer of securities by GAP after consummation of the transactions described in the December Purchase Agreement (except that this clause A shall pertain only until such time as GAP has Beneficial Ownership of less than fifteen percent (15%) of the outstanding shares of Common Stock); provided, that any shares of Common Stock Beneficially Owned by one or more officers or directors of the Company where (x) such officers or directors are also included within the term “GAP” and (y) such shares of Common Stock were distributed directly by the Company to such officers or directors as equity-based compensation, shall be excluded from the calculation of the Beneficial Ownership of GAP for purposes of the definition of “Acquiring Person” if the inclusion of such shares of Common Stock in such calculation, by itself, would otherwise cause GAP to be an Acquiring Person;

B. Cenwell Limited, Campina Enterprises Limited, Great Affluent Limited, Lion Cosmos Limited and Dragonfield Limited (referred to collectively with their respective Affiliates and Associates as “Cenwell”) so long as Cenwell does not increase (other than an increase resulting solely from a reduction of the number of shares of outstanding Common Stock, including by reason of repurchases of Common Stock or Exchangeable Shares by the Company, or a dividend or distribution paid or made by the Company or Exchangeco on, or a split or subdivision of, any shares of their respective capital stock) its Beneficial Ownership of Common Stock to a percentage of the outstanding shares of Common Stock at any time that is greater than: (1) the percentage of the outstanding shares of Common Stock represented by the sum of (x) the shares as to which Cenwell has Beneficial Ownership as of the close of business on December 29, 2004, assuming, for purposes of this calculation, all warrants and other

3

securities convertible into or exercisable for Common Stock, or any other rights to purchase Common Stock, in all cases where held or enjoyed by Cenwell, are immediately convertible or exercisable, plus (y) the shares as to which Cenwell obtains (or is entitled to obtain) Beneficial Ownership directly from the Company pursuant to the consummation of the transactions described in the December Purchase Agreement; or (2) such lesser percentage as to which Cenwell has Beneficial Ownership following any transfer of securities by Cenwell after consummation of the transactions described in the December Purchase Agreement (except that this clause B. shall pertain only until such time as Cenwell has Beneficial Ownership of less than fifteen percent (15%) of the outstanding shares of Common Stock);

C. Vectis CP Holdings, LLC (referred to collectively with its Affiliates and Associates as “Vectis”) so long as Vectis does not increase (other than an increase resulting solely from a reduction of the number of shares of outstanding Common Stock, including by reason of repurchases of Common Stock or Exchangeable Shares by the Company, or a dividend or distribution paid or made by the Company or Exchangeco on, or a split or subdivision of, any shares of their respective capital stock) its Beneficial Ownership of Common Stock to a percentage of the outstanding shares of Common Stock at any time that is greater than: (1) the percentage of the outstanding shares of Common Stock represented by the sum of (x) the shares as to which Vectis has Beneficial Ownership as of the close of business on November 7, 2001 (if any), plus (y) the shares as to which Vectis obtains Beneficial Ownership directly from the Company pursuant to the consummation of the transactions described in that certain Stock and Warrant Purchase and Exchange Agreement (the “2001 Purchase Agreement”), dated November 7, 2001, by and among the Company and the “Purchasers” named therein, plus (z) the shares as to which Vectis obtains Beneficial Ownership directly from the Company pursuant to the rights offering for an aggregate amount up to $21,000,000 of Series E Preferred Stock of the Company pursuant to which the Company will distribute transferable rights to certain holders of Common Stock; or (2) such lesser percentage as to which Vectis has Beneficial Ownership following any transfer of securities by Vectis after consummation of the transactions described in the 2001 Purchase Agreement (except that this clause C. shall pertain only until such time as Vectis has Beneficial Ownership of less than fifteen percent (15%) of the outstanding shares of Common Stock); provided, that any shares of Common Stock Beneficially Owned by one or more officers or directors of the Company where (x) such officers or directors are also included within the term “Vectis” and (y) such shares of Common Stock were distributed

4

directly by the Company to such officers or directors as equity-based compensation, shall be excluded from the calculation of the Beneficial Ownership of Vectis for purposes of the definition of “Acquiring Person” if the inclusion of such shares of Common Stock in such calculation, by itself, would otherwise cause Vectis to be an Acquiring Person;

D. Permal U.S. Opportunities Limited, Zaxis Equity Neutral, L.P., Zaxis Institutional Partners, L.P., Zaxis Offshore Limited and Zaxis Partners, L.P., (referred to collectively with their Affiliates and Associates as “Apex”) so long as Apex does not increase (other than an increase resulting solely from a reduction of the number of shares of outstanding Common Stock, including by reason of repurchases of Common Stock or Exchangeable Shares by the Company, or a dividend or distribution paid or made by the Company or Exchangeco on, or a split or subdivision of, any shares of their respective capital stock) its Beneficial Ownership of Common Stock to a percentage of the outstanding shares of Common Stock at any time that is greater than: (1) the percentage of the outstanding shares of Common Stock represented by the sum of (x) the shares as to which Apex has Beneficial Ownership as of the close of business on January 16, 2004, assuming, for purposes of this calculation, all warrants and other securities convertible into or exercisable for Common Stock, or any other rights to purchase Common Stock, in all cases where held or enjoyed by Apex, are immediately convertible or exercisable, plus (y) the shares as to which Apex obtains (or is entitled to obtain) Beneficial Ownership directly from the Company pursuant to the consummation of the transactions described in the Convertible Note Purchase Agreement (the “January Purchase Agreement”), dated January 16, 2004, by and among the Company and the “Lenders” party thereto, including, without limitation, the Issuable Shares or the Common Shares (each as defined in the January Purchase Agreement), plus (z) the shares as to which Apex obtains (or is entitled to obtain) Beneficial Ownership directly from the Company pursuant to the consummation of the transactions described in the Convertible Note Purchase Agreement (the “March Purchase Agreement”), dated March 9, 2004, by and among the Company and the “Lenders” party thereto, including, without limitation, the Issuable Shares or the Common Shares (each as defined in the March Purchase Agreement); or (2) such lesser percentage as to which Apex has Beneficial Ownership following any transfer of securities by Apex after consummation of the transactions described in the February Purchase Agreement (except that this clause D. shall pertain only until such time as Apex has Beneficial Ownership of less than fifteen percent (15%) of the outstanding shares of Common Stock).”

5

E. Peter Kellner (referred to collectively with his Affiliates and Associates as “Kellner”) so long as Kellner does not increase (other than an increase resulting solely from a reduction of the number of shares of outstanding Common Stock, including by reason of repurchases of Common Stock or Exchangeable Shares by the Company, or a dividend or distribution paid or made by the Company or Exchangeco on, or a split or subdivision of, any shares of their respective capital stock) its Beneficial Ownership of Common Stock to a percentage of the outstanding shares of Common Stock at any time that is greater than: (1) the percentage of the outstanding shares of Common Stock represented by the sum of (x) the shares as to which Kellner has Beneficial Ownership as of the close of business on December 29, 2004, assuming, for purposes of this calculation, all warrants and other securities convertible into or exercisable for Common Stock, or any other rights to purchase Common Stock, in all cases where held or enjoyed by Kellner, are immediately convertible or exercisable, plus (y) the shares as to which Kellner obtains (or is entitled to obtain) Beneficial Ownership directly from the Company pursuant to the consummation of the transactions described in the December Purchase Agreement; or (2) such lesser percentage as to which Kellner has Beneficial Ownership following any transfer of securities by Kellner after consummation of the transactions described in the December Purchase Agreement (except that this clause E. shall pertain only until such time as Kellner has Beneficial Ownership of less than fifteen percent (15%) of the outstanding shares of Common Stock).”

The undersigned officer of the Company, being an appropriate officer of the Company and authorized to do so by resolution of the board of directors of the Company, hereby certifies to the Rights Agent that this Amendment is in compliance with the terms of Section 27 of the Agreement.

This Amendment may be executed in any number of counterparts, each of which shall be deemed an original, and all of which together shall constitute one instrument.

[the remainder of this page intentionally left blank]

6

IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be duly executed as of the day and year first above written.

CRITICAL PATH, INC.
By	/s/ Michael J. Zukerman
Name:	Michael J. Zukerman
Title:	General Counsel and Senior Vice President

COMPUTERSHARE TRUST COMPANY, INC.
By	/s/ Zachary DeLisa
Name:	Zachary DeLisa
Title:	Operations Manager
COMPUTERSHARE TRUST COMPANY, INC.
By	/s/ John M. Wahl
Name:	John M. Wahl
Title:	Corporate Trust Officer

COUNTERPART SIGNATURE PAGE TO AMENDMENT TO PREFERRED STOCK RIGHTS AGREEMENT

EX-10.1

Exhibit 10.1

NOTE AND WARRANT PURCHASE AGREEMENT

among

CRITICAL PATH, INC.,

GENERAL ATLANTIC PARTNERS 74, L.P.,

GAPSTAR, LLC,

GAP COINVESTMENT PARTNERS II, L.P.,

GAPCO GMBH & CO. KG,

CAMPINA ENTERPRISES LIMITED,

AND

RICHMOND III, LLC

Dated: December 29, 2004

Table of Contents

Page

ARTICLE I DEFINITIONS		1
1.1	Definitions	1
ARTICLE II PURCHASE AND SALE OF NOTES AND WARRANTS		9
2.1	Purchase and Sale of Notes and Warrants	9
2.2	Filings	9
2.3	Certificate of Determination	9
2.4	Closings; Deliveries	9
ARTICLE III REPRESENTATIONS AND WARRANTIES OF THE COMPANY		11
3.1	Corporate Existence and Power	11
3.2	Authorization; No Contravention	12
3.3	Governmental Authorization; Third Party Consents	12
3.4	Binding Effect	12
3.5	Litigation	12
3.6	Compliance with Laws	13
3.7	Capitalization	13
3.8	No Default or Breach; Contractual Obligations	14
3.9	Title to Properties	15
3.10	Reports; Financial Statements	15
3.11	Taxes	15
3.12	No Material Adverse Change; Ordinary Course of Business	16
3.13	Private Offering	16
3.14	Labor Relations	16
3.15	Employee Benefit Plans	17
3.16	Liabilities	18
3.17	Affiliate Transactions	18
3.18	Intellectual Property	18
3.19	Privacy of Customer Information	20
3.20	Potential Conflicts of Interest	20
3.21	Trade Relations	20
3.22	Outstanding Borrowing	20
3.23	Broker’s, Finder’s or Similar Fees	21
3.24	CCC Section	21
3.25	Disclosure	21
3.26	Investments	21
3.27	Sarbanes-Oxley Compliance	21
ARTICLE IV REPRESENTATIONS AND WARRANTIES OF THE INVESTORS		22
4.1	Existence and Power	22
4.2	Authorization; No Contravention	23

i

4.3	Governmental Authorization; Third Party Consents	23
4.4	Binding Effect	23
4.5	Purchase for Own Account	23
4.6	Restricted Securities	24
4.7	Accredited Investor	24
4.8	Experience	24
4.9	Access to Information	24
4.10	General Solicitation	25
4.11	Reliance	25
ARTICLE V CONDITIONS TO INITIAL CLOSING		25
5.1	Conditions to Investors’ Obligations	25
5.2	Conditions to Company’s Obligations	26
ARTICLE VI CONDITIONS TO SECOND CLOSING		27
6.1	Conditions to Investors’ Obligations	27
6.2	Conditions to Company’s Obligations	28
ARTICLE VII INDEMNIFICATION		29
7.1	Indemnification	29
7.2	Notification	29
7.3	Contribution	30
ARTICLE VIII COVENANTS		31
8.1	Financial Statements and Other Information	31
8.2	FIRPTA Certificate	31
8.3	Reservation of Series F Preferred Stock and Common Stock	32
ARTICLE IX TERMINATION		32
9.1	Termination	32
ARTICLE X MISCELLANEOUS		33
10.1	Survival of Representations and Warranties	33
10.2	Notices	33
10.3	Successors and Assigns; Third Party Beneficiaries	35
10.4	Amendment and Waiver	35
10.5	Counterparts	35
10.6	Richmond III Registration Rights	35
10.7	Coinvestor Sub-Group Board Seat	36
10.8	Observer Rights	36
10.9	Certain Series F Preferred Stock Terms	36
10.10	Headings	37
10.11	Governing Law	37
10.12	Severability	37
10.13	Rules of Construction	37
10.14	Entire Agreement	37
10.15	Fees	37
10.16	Publicity; Confidentiality	37
10.17	Further Assurances	38

ii

EXHIBITS

A	Form of Note
B	Form of Warrant
C	Articles of Incorporation
D	By-laws
E	Form of Series F Certificate of Determination
F	Form of Paul, Hastings, Janofsky & Walker, LLP Opinion

SCHEDULES

2.1(a)	Purchased Notes and Warrants at Initial Closing
2.1(b)	Purchased Notes and Warrants at Second Closing
3.3	Governmental Authorization and Third Party Consents
3.5	Claims
3.7(a)	Capitalization
3.10(a)	SEC Reports
3.12	Material Adverse Changes
3.17	Affiliate Transactions
3.20	Conflicts of Interest
3.22	Indebtedness
3.26	Investments

iii

NOTE AND WARRANT PURCHASE AGREEMENT

NOTE AND WARRANT PURCHASE AGREEMENT, dated December 29, 2004 (this “Agreement”), among General Atlantic Partners 74, L.P., a Delaware limited partnership, GapStar, LLC, a Delaware limited liability company, GAP Coinvestment Partners II, L.P., a Delaware limited partnership, GAPCO GmbH & Co. KG, a German limited partnership, Campina Enterprises Limited (“Campina”), and Richmond III, LLC (collectively, the “Investors”) and Critical Path, Inc., a California corporation (the “Company”),

WHEREAS, upon the terms and conditions set forth in this Agreement, the Company proposes to issue and sell to the Investors, at the Initial Closing (as hereinafter defined), (i) senior notes, substantially in the form attached hereto as Exhibit A (each a “Note” and, collectively, the “Notes”) having an aggregate principal amount of eleven million dollars ($11,000,000), allocated among each Investor in the principal amount set forth opposite such Investor’s name on Schedule 2.1(a) hereto and (ii) warrants, substantially in the form attached hereto as Exhibit B (each a “Warrant” and, collectively, the “Warrants”) to purchase, subject to the terms and conditions thereof, the aggregate number of shares of the Company’s Series F Redeemable Convertible Preferred Stock, $0.001 par value per share (the “Series F Preferred Stock”) set forth opposite each Investor’s name on Schedule 2.1(a) hereto, at an exercise price per share equal to $14.00 (the “Warrant Exercise Price”); and

WHEREAS, upon the terms and conditions set forth in this Agreement, the Company proposes to issue and sell to the Investors, at the Second Closing, (i) Notes having an aggregate principal amount of seven million dollars ($7,000,000), allocated among each Investor in the principal amount set forth opposite such Investor’s name on Schedule 2.1(b) hereto and (ii) Warrants to purchase, subject to the terms and conditions thereof, the aggregate number of shares of Series F Preferred Stock set forth opposite each Investor’s name on Schedule 2.1(b) hereto, at the Warrant Exercise Price.

NOW, THEREFORE, in consideration of the mutual covenants and agreements set forth herein and for good and valuable consideration, the receipt and adequacy of which are hereby acknowledged, the parties hereto agree as follows:

ARTICLE I

DEFINITIONS

1.1 Definitions. As used in this Agreement, and unless the context requires a different meaning, the following terms have the meanings indicated:

“Affiliate” shall mean any Person who is an “affiliate” as defined in Rule 12b-2 of the General Rules and Regulations under the Exchange Act.

“Agreement” means this Agreement as the same may be amended, supplemented or modified in accordance with the terms hereof.

“Registration Rights Agreement” means the Company’s Third Amended and Restated Registration Rights Agreement, dated as of March 9, 2004.

“Amendment to Preferred Stock Rights Agreement” means an amendment to the Company’s Preferred Stock Rights Agreement to permit the Investors to purchase the Warrants hereunder without causing such Investors to become Acquiring Persons (as defined in the Preferred Stock Rights Agreement).

“Articles of Incorporation” means the Amended and Restated Articles of Incorporation of the Company in effect on the Initial Closing Date and attached hereto as Exhibit C.

“Board of Directors” means the Board of Directors of the Company.

“Business Day” means any day other than a Saturday, Sunday or other day on which commercial banks in the State of New York or the State of California are authorized or required by law or executive order to close.

“By-laws” means the by-laws of the Company in effect on the Initial Closing Date and attached hereto as Exhibit D.

“CK Purchasers” means Campina Enterprises Limited, Cenwell Limited, Great Affluent Limited, Dragonfield Limited and Lion Cosmos Limited and their transferees.

“Claims” has the meaning set forth in Section 3.5 of this Agreement.

“Code” means the Internal Revenue Code of 1986, as amended, or any successor statute thereto.

“Commission” means the United States Securities and Exchange Commission or any similar agency then having jurisdiction to enforce the Securities Act and Exchange Act.

“Common Stock” means the common stock of the Company, par value $0.001 per share.

“Common Stock Warrant” or “Common Stock Warrants,” as the case may be, means those certain warrants to purchase Common issued to General Atlantic Entities pursuant to that certain Stock and Warrant Purchase and Exchange Agreement, dated as of November 8, 2001.

“Commonly Controlled Entity” means any entity which is under common control with the Company within the meaning of Code Section 414(b), (c), (m), (o) or (t).

2

“Common Shares” means the shares of Common Stock issuable on conversion of the shares of Series F Preferred Stock.

“Company” has the meaning set forth in the preamble to this Agreement.

“Company Plans” has the meaning set forth in Section 3.15 of this Agreement.

“Condition of the Company” means the assets, business, properties, operations or condition (financial or otherwise) of the Company and its Subsidiaries, taken as a whole.

“Contingent Obligation” means, as applied to any Person, any direct or indirect liability of that Person with respect to any Indebtedness, lease, dividend, guaranty, letter of credit or other obligation, contractual or otherwise (the “primary obligation”) of another Person (the “primary obligor”), whether or not contingent, (a) to purchase, repurchase or otherwise acquire such primary obligations or any property constituting direct or indirect security therefor, (b) to advance or provide funds (i) for the payment or discharge of any such primary obligation, or (ii) to maintain working capital or equity capital of the primary obligor or otherwise to maintain the net worth or solvency or any balance sheet item, level of income or financial condition of the primary obligor, (c) to purchase property, securities or services primarily for the purpose of assuring the owner of any such primary obligation of the ability of the primary obligor to make payment of such primary obligation, or (d) otherwise to assure or hold harmless the owner of any such primary obligation against loss or failure or inability to perform in respect thereof. The amount of any Contingent Obligation shall be deemed to be an amount equal to the stated or determinable amount of the primary obligation in respect of which such Contingent Obligation is made or, if not stated or determinable, the maximum reasonably anticipated liability in respect thereof.

“Contractual Obligations” means, as to any Person, any provision of any security issued by such Person or of any agreement, undertaking, contract, indenture, mortgage, deed of trust or other instrument to which such Person is a party or by which it or any of its property is bound.

“Conversion” has the meaning set forth in Section 2.1(a).

“Conversion Notice” has the meaning set forth in Section 2.5 of this Agreement.

“Copyrights” means any foreign or United States copyright registrations and applications for registration thereof, and any non-registered copyrights.

“Environmental Laws” means federal, state, local and foreign laws, principles of common laws, civil laws, regulations, and codes, as well as orders, decrees, judgments or injunctions, issued, promulgated, approved or entered thereunder relating to pollution, protection of the environment or public health and safety.

3

“ERISA” means the Employee Retirement Income Security Act of 1974, as amended.

“Exchange Act” means the Securities Exchange Act of 1934, as amended, and the rules and regulations of the Commission thereunder.

“Financial Statements” has the meaning set forth in Section 3.10 of this Agreement.

“GAAP” means United States generally accepted accounting principles in effect from time to time.

“General Atlantic Entities” means General Atlantic Partners 74, L.P., a Delaware limited partnership, GAP Coinvestment Partners II, L.P., a Delaware limited partnership, GapStar, LLC, a Delaware limited liability company, and GAPCO GmbH & Co. KG, a German limited partnership.

“Governmental Authority” means the government of any nation, state, city, locality or other political subdivision thereof, any entity exercising executive, legislative, judicial, regulatory or administrative functions of or pertaining to government, and any corporation or other entity owned or controlled, through stock or capital ownership or otherwise, by any of the foregoing.

“Indebtedness” means, as to any Person, (a) all obligations of such Person for borrowed money (including, without limitation, reimbursement and all other obligations with respect to surety bonds, letters of credit and bankers’ acceptances, whether or not matured), (b) all obligations of such Person to pay the deferred purchase price of property or services, except trade accounts payable and accrued commercial or trade liabilities arising in the ordinary course of business, (c) all interest rate and currency swaps, caps, collars and similar agreements or hedging devices under which payments are obligated to be made by such Person, whether periodically or upon the happening of a contingency, (d) all indebtedness created or arising under any conditional sale or other title retention agreement with respect to property acquired by such Person (even though the rights and remedies of the seller or Investor under such agreement in the event of default are limited to repossession or sale of such property), (e) all obligations of such Person under leases which have been or should be, in accordance with GAAP, recorded as capital leases, (f) all indebtedness secured by any Lien (other than Permitted Liens) on any property or asset owned or held by that Person regardless of whether the indebtedness secured thereby shall have been assumed by that Person or is non-recourse to the credit of that Person, and (g) any Contingent Obligation of such Person.

“Indemnified Party” has the meaning set forth in Section 7.1 of this Agreement.

“Indemnifying Party” has the meaning set forth in Section 7.1 of this Agreement.

4

“Initial Closing” has the meaning set forth in Section 2.4(a) of this Agreement.

“Initial Closing Date” has the meaning set forth in Section 2.4(a) of this Agreement.

“Intellectual Property” has the meaning set forth in Section 3.18 of this Agreement.

“Internet Assets” means any Internet domain names and other computer user identifiers and any rights in and to sites on the worldwide web, including rights in and to any text, graphics, audio and video files and html or other code incorporated in such sites.

“Investment” means (i) the acquisition (whether for cash, property, services, assumption of Indebtedness, securities or otherwise) of assets (other than equipment, inventory, supplies or other assets acquired in the ordinary course of business of the Company), capital stock, bonds, notes, debentures, partnership, joint venture or other ownership interests or other securities of any Person, (ii) any deposit with, or advance, loan or other extension of credit to, or on behalf of, any Person (other than deposits made in connection with the purchase of equipment, inventory, services, leases, supplies or other assets in the ordinary course of business of the Company), (iii) any other capital contribution to or investment in such Person, including, without limitation, any guaranty obligation incurred for the benefit of such Person. For the sake of clarity, Investments shall include any transfer of property or assets by the Company to any of its Subsidiaries or by any Subsidiary of the Company to any other Subsidiary.

“IP Agreements” has the meaning set forth in Section 3.18(a)(iii) of this Agreement.

“Knowledge” means the knowledge of the Company and Chief Executive Officer, Chief Financial Officer, and Senior Vice President, General Counsel of the Company (who are Mark J. Ferrer, James Clark and Michael J. Zukerman) after due inquiry.

“Liabilities” has the meaning set forth in Section 3.16 of this Agreement.

“Lien” means any mortgage, deed of trust, pledge, hypothecation, assignment, encumbrance, lien (statutory or other) or preference, priority, right or other security interest or preferential arrangement of any kind or nature whatsoever (excluding preferred stock and equity related preferences).

“Losses” has the meaning set forth in Section 7.1 of this Agreement.

“Material Contractual Obligations” has the meaning set forth in Section 3.8 of this Agreement.

5

“NASD Rules” has the meaning set forth in Section 3.27(b).

“Nasdaq” means The Nasdaq Stock Market, Inc.

“Notes” has the meaning set forth in the recitals to this Agreement.

“Orders” has the meaning set forth in Section 3.2 of this Agreement.

“Patents” means any foreign or United States patents and patent applications, including any divisions, continuations, continuations-in-part, substitutions or reissues thereof, whether or not patents are issued on such applications and whether or not such applications are modified, withdrawn or resubmitted.

“Permitted Investments” means (i) Investments in cash or cash equivalents, (ii) accounts receivable created, acquired or made in the ordinary course of business and payable or dischargeable in accordance with customary trade terms; (iii) Investments existing on the Initial Closing Date, and listed on Schedule 3.26 hereto, (iv) loans to employees, directors or officers of the Company in connection with the award of convertible bonds or capital stock under a stock incentive plan, stock option plan or other equity-based compensation plan or arrangement, (v) other advances or loans to employees, directors, officers or agents of the Company in the ordinary course of business not to exceed $500,000 in the aggregate at any time outstanding; (vi) loans, advances and Investments in or by foreign Subsidiaries; (vii) any acquisition for which the prior written consent of the holders of a majority of the outstanding principal amount of Notes issued by the Company pursuant to this Agreement has been obtained, or (viii) other loans, advances and investments of a nature not contemplated by the foregoing sections in an amount not to exceed $500,000 in the aggregate at any time outstanding.

“Permitted Liens” has the meaning set forth in the Note.

“Person” means any individual, firm, corporation, partnership, trust, incorporated or unincorporated association, joint venture, joint stock company, limited liability company, Governmental Authority or other entity of any kind, and shall include any successor (by merger or otherwise) of such entity.

“Plan” means any employee benefit plan, arrangement, policy, program, agreement or commitment (whether or not an employee plan within the meaning of Section 3(3) of ERISA), including, without limitation, any employment, consulting or deferred compensation agreement, executive compensation, bonus, incentive, pension, profit-sharing, savings, retirement, stock option, stock purchase or severance pay plan, any life, health, disability or accident insurance plan, whether oral or written, whether or not subject to ERISA, as to which the Company or any Commonly Controlled Entity has or in the future could have any direct or indirect, actual or contingent liability.

“Requirements of Law” means, as to any Person, any law (including Environmental Laws), statute, treaty, rule, regulation, right, privilege, qualification,

6

license or franchise or determination of an arbitrator or a court or other Governmental Authority or stock exchange, in each case applicable or binding upon such Person or any of its property or to which such Person or any of its property is subject or pertaining to any or all of the transactions contemplated or referred to herein.

“Retiree Welfare Plan” means any welfare plan (as defined in Section 3(1) of ERISA) that provides benefits to current or former employees beyond their retirement or other termination of service (other than coverage mandated by Section 4980A of the Code, commonly referred to as “COBRA,” the cost of which is fully paid by the current or former employee or his or her dependents).

“Richmond III” means Richmonds III, LLC.

“Sarbanes-Oxley Act” has the meaning set forth in Section 3.27(a) of this Agreement.

“SEC Reports” has the meaning set forth in Section 3.10 of this Agreement.

“Securities” has the meaning set forth in Section 4.8 of this Agreement.

“Securities Act” means the Securities Act of 1933, as amended, and the rules and regulations of the Commission thereunder.

“Second Closing” has the meaning set forth in Section 2.4(b) of this Agreement.

“Second Closing Date” has the meaning set forth in Section 2.4(b) of this Agreement.

“Series D Preferred Stock” means the Series D Cumulative Redeemable Convertible Preferred Stock of the Company, par value $0.001 per share.

“Series F Certificate of Determination” means the Certificate of Determination of Preferences of Series F Redeemable Convertible Preferred Stock, substantially in the form attached hereto as Exhibit E.

“Series E Preferred Stock” means the Series E Redeemable Convertible Preferred Stock of the Company, par value $0.001 per share.

“Series F Preferred Stock” has the meaning set forth in the recitals to this Agreement.

“Software” means any computer software programs, source code, object code, data and documentation, including, without limitation, any computer software programs that incorporate and run the Company’s pricing models, formulae and algorithms.

7

“Stock Equivalents” means any security or obligation which is by its terms convertible into or exchangeable or exercisable for shares of common stock or other capital stock of the Company, and any option, warrant or other subscription or purchase right with respect to common stock or such other capital stock.

“Stock Option Plans” means the Company’s stock option plans and employee purchase plans pursuant to which shares of restricted stock and options to purchase shares of Common Stock are reserved and available for grant to officers, directors, employees and consultants of the Company.

“Stockholders Agreement” means the Amended and Restated Stockholders Agreement, dated as of November 26, 2003, by and among the Company and the parties named therein.

“Subsidiaries” means, as of the relevant date of determination, with respect to any Person, a corporation or other Person of which 50% or more of the voting power of the outstanding voting equity securities or 50% or more of the outstanding economic equity interest is held, directly or indirectly, by such Person. Unless otherwise qualified, or the context otherwise requires, all references to a “Subsidiary” or to “Subsidiaries” in this Agreement shall refer to a Subsidiary or Subsidiaries of the Company.

“Taxes” means any federal, state, provincial, county, local, foreign and other taxes (including, without limitation, income, profits, windfall profits, alternative, minimum, accumulated earnings, personal holding company, capital stock, premium, estimated, excise, sales, use, occupancy, gross receipts, franchise, ad valorem, severance, capital levy, production, transfer, withholding, employment, unemployment compensation, payroll and property taxes, import duties and other governmental charges and assessments), whether or not measured in whole or in part by net income, and including deficiencies, interest, additions to tax or interest, and penalties with respect thereto, and including expenses associated with contesting any proposed adjustments related to any of the foregoing.

“Trade Secrets” means any trade secrets, research records, processes, procedures, manufacturing formulae, technical know-how, technology, blue prints, designs, plans, inventions (whether patentable and whether reduced to practice), invention disclosures and improvements thereto.

“Trademarks” means any foreign or United States trademarks, service marks, trade dress, trade names, brand names, designs and logos, corporate names, product or service identifiers, whether registered or unregistered, and all registrations and applications for registration thereof.

“Transaction Documents” means, collectively, this Agreement, the Notes, the Warrants, the Amendment to the Preferred Stock Rights Agreement and the Waivers.

8

“Waivers” means the waivers and consents, dated the date hereof, executed by (i) the requisite holders of the Company’s Series D Preferred Stock and (ii) the requisite General Atlantic Entities, CK Purchasers and Vectis CP Holdings, LLC, in each case to consent to and approve, to the extent necessary, the transactions and agreements contemplated by the Transaction Documents and to waive any rights they may have under that certain Amended and Restated Stockholders Agreement, dated November 26, 2003.

“Warrant” or “Warrants,” as the case may be, has the meaning set forth in the recitals to this Agreement.

“Warrant Exercise Price” has the meaning set forth in the recitals to this Agreement.

“Warrant Shares” means the shares of Series F Preferred Stock issuable upon exercise of the Warrants.

ARTICLE II

PURCHASE AND SALE OF NOTES AND WARRANTS

2.1 Purchase and Sale of Notes and Warrants. Subject to the terms and conditions of this Agreement, (a) on the Initial Closing Date, each of the Investors, severally and not jointly, agrees to purchase, and the Company agrees to sell and issue to each Investor, (i) a Note, in the aggregate principal amount set forth opposite such Investor’s name on Schedule 2.1(a) hereto and (ii) a Warrant to purchase the aggregate number of shares of Series F Preferred Stock set forth opposite such Investor’s name on Schedule 2.1(a) hereto and (b) on the Second Closing Date, each of the Investors, severally and not jointly, agrees to purchase, and the Company agrees to sell and issue to each Investor, (i) a Note, in the aggregate principal amount set forth opposite such Investor’s name on Schedule 2.1(b) hereto and (ii) a Warrant to purchase the aggregate number of shares of Series F Preferred Stock set forth opposite such Investor’s name on Schedule 2.1(b) hereto. Each of the Notes shall be due and payable upon the terms and conditions set forth in the Notes and herein. All payments by the Company under the Notes of principal and interest shall be as set forth in the Notes.

2.2 Filings. Upon the terms and conditions of this Agreement, on the Initial Closing Date, the Company shall file with the Secretary of State of the State of California the Series F Certificate of Determination.

2.3 Certificate of Determination. The Series F Preferred Stock shall have the preferences and rights set forth in the Series F Certificate of Determination.

2.4 Closings; Deliveries.

(a) Initial Closing. Subject to the terms and conditions of this Agreement, the initial purchase and sale of the Notes and Warrants contemplated by

9

Section 2.1(a) of this Agreement (the “Initial Closing”) shall be held on December 30, 2004 (the “Initial Closing Date”), at the offices of Paul, Hastings, Janofsky & Walker, LLP, 55 Second Street, San Francisco, California, or at such other time and place as the Company and the Investors may mutually agree. At the Initial Closing, signature pages transmitted by facsimile will be acceptable, with originals to immediately follow.

(b) Second Closing. Subject to the terms and conditions of this Agreement, the second purchase and sale of the Notes and Warrants contemplated by Section 2.1(b) of this Agreement (the “Second Closing”) shall be held on the third Business Day after the last to occur of the satisfaction or waiver by the Investors of the conditions set forth in Section 6.1 and the satisfaction or waiver by the Company of the conditions set forth in Section 6.2 (the “Second Closing Date”), at the offices of Paul, Hastings, Janofsky & Walker, LLP, 55 Second Street, San Francisco, California, or at such other time and place as the Company and the Investors may mutually agree. At the Second Closing, signature pages transmitted by facsimile will be acceptable, with originals to immediately follow.

(c) Deliveries by the Company at the Initial Closing. At the Initial Closing, subject to the terms and conditions hereof, the Company shall execute and deliver to each Investor:

(i) a duly executed Note representing the aggregate principal amount set forth opposite such Investor’s name on Schedule 2.1(a), a duly executed Warrant to purchase the aggregate number of shares of Series F Preferred Stock set forth opposite such Investor’s name on Schedule 2.1(a) and each of the other Transaction Documents to which the Company is a party; and

(ii) such other documentation required to be provided by the Company pursuant to Section 5.1.

(d) Deliveries by each Investor at the Initial Closing. At the Initial Closing, subject to the terms and conditions hereof, each Investor shall:

(i) execute and deliver to the Company each of the other Transaction Documents to which it is a party; and

(ii) pay the aggregate purchase price for the Notes and the Warrants to be purchased at the Initial Closing, by wire transfer, in the aggregate amount set forth opposite such Investor’s name on Schedule 2.1(a) to the following account (the “Account”):

Silicon Valley Bank

3003 Tasman Dr

Santa Clara, CA 95054

Tel: 415-512-4224

10

Account Name:	Critical Path, Inc.
	350 The Embarcadero 6th Floor San Francisco, CA 95648

Bank Acct: 3300229151

ABA: 121140399

SWIFT CODE: SVBKUS6S

(e) Deliveries by the Company at the Second Closing. At the Second Closing, subject to the terms and conditions hereof, the Company shall execute and deliver to each Investor a duly executed Note representing the aggregate principal amount set forth opposite such Investor’s name on Schedule 2.1(b), a duly executed Warrant to purchase the aggregate number of shares of Series F Preferred Stock set forth opposite such Investor’s name on Schedule 2.1(b) and such documentation required to be provided by the Company pursuant to Section 6.1.

(f) Deliveries by each Investor at the Second Closing. At the Second Closing, subject to the terms and conditions hereof, each Investor shall pay the aggregate purchase price for the Notes and the Warrants to be purchased at the Second Closing by wire transfer to the Account, in the aggregate amount set forth opposite such Investor’s name on Schedule 2.1(b).

ARTICLE III

REPRESENTATIONS AND WARRANTIES OF THE COMPANY

The Company represents and warrants to each of the Investors that, except as disclosed or incorporated by reference in the SEC Reports or the Disclosure Schedules:

3.1 Corporate Existence and Power. The Company and each of its Subsidiaries (a) is a corporation duly organized, validly existing and in good standing under the laws of the jurisdiction of its incorporation; (b) has all requisite corporate power and authority to own and operate its property, to lease the property it operates as lessee and to conduct the business in which it is currently engaged; (c) is duly qualified as a foreign corporation, licensed and in good standing under the laws of each jurisdiction in which its ownership, lease or operation of property or the conduct of its business requires such qualification, except where the failure to be so qualified could not reasonably be expected to have a material adverse effect on the Condition of the Company and (d) has the corporate power and authority to execute, deliver and perform its obligations under this Agreement and each of the other Transaction Documents. No jurisdiction, other than those referred to in clause (c) above, has claimed, in writing or otherwise, that the Company or any of its Subsidiaries is required to qualify as a foreign corporation or other entity therein, and the Company or any of its Subsidiaries does not file any franchise,

11

income or other tax returns in any other jurisdiction based upon the ownership or use of property therein or the derivation of income therefrom.

3.2 Authorization; No Contravention. The execution, delivery and performance by the Company of this Agreement and each of the other Transaction Documents and the transactions contemplated hereby and thereby (a) have been duly authorized by all necessary corporate action of the Company; (b) do not contravene the terms of the Articles of Incorporation or the By-laws; (c) do not violate, conflict with or result in any breach, default or contravention of (or with due notice or lapse of time or both would result in any breach, default or contravention of), or the creation of any Lien under, any Contractual Obligation of the Company or any of its Subsidiaries or any Requirement of Law applicable to the Company or any of its Subsidiaries except such violations or conflicts that would not reasonably be expected to have a material adverse effect on the Condition of the Company; and (d) do not violate any judgment, injunction, writ, award, decree or order of any nature (collectively, “Orders”) of any Governmental Authority against, or binding upon, the Company or any of its Subsidiaries.

3.3 Governmental Authorization; Third Party Consents. Except as set forth in Schedule 3.3, no approval, consent, compliance, exemption, authorization or other action by, or notice to, or filing with, any Governmental Authority or any other Person, and no lapse of a waiting period under a Requirement of Law, is necessary or required in connection with the execution, delivery or performance (including, without limitation, the sale, issuance and delivery of the Warrants, the Warrant Shares or the Common Shares) by, or enforcement against, the Company of this Agreement and the other Transaction Documents or the transactions contemplated hereby and thereby, other than (a) the notification to The NASDAQ National Market for the listing of the shares of Common Shares and applicable blue-sky filings, (b) such as have already been obtained or such exemptive filings as may be required under applicable securities laws, and (c) such other filings as may be required following the Initial Closing Date or the Second Closing Date under the Exchange Act.

3.4 Binding Effect. This Agreement and each of the other Transaction Documents to which the Company is a party have been duly executed and delivered by the Company, and this Agreement and each of the other Transaction Documents to which the Company is a party constitute the legal, valid and binding obligations of the Company, enforceable against the Company in accordance with their terms, except as enforceability may be limited by applicable bankruptcy, insolvency, reorganization, fraudulent conveyance or transfer, moratorium or similar laws affecting the enforcement of creditors’ rights generally and by general principles of equity relating to enforceability (regardless of whether considered in a proceeding at law or in equity).

3.5 Litigation. Except as set forth on Schedule 3.5, there are no actions, suits, proceedings, claims, complaints, disputes, arbitrations or investigations

12

(collectively, “Claims”) pending or, to the Knowledge of the Company, threatened, at law, in equity, in arbitration or before any Governmental Authority against the Company or any of its Subsidiaries that seeks in excess of $50,000 in damages nor is the Company aware that there is any basis for any of the foregoing. The foregoing includes, without limitation, Claims pending or, to the Knowledge of the Company, threatened or any basis therefor known by the Company involving the prior employment of any employee of the Company or any of its Subsidiaries, their use in connection with the business of the Company or any of its Subsidiaries of any information or techniques allegedly proprietary to any of their former employers or their obligations under any agreements with prior employers. No Order has been issued by any court or other Governmental Authority against the Company or any of its Subsidiaries purporting to enjoin or restrain the execution, delivery or performance of this Agreement or any of the other Transaction Documents.

3.6 Compliance with Laws. The Company and each of its Subsidiaries is in compliance in all material respects with all Requirements of Law and all Orders issued by any court or Governmental Authority against the Company in all respects. To the Company’s Knowledge, there are no Requirements of Law which could reasonably be expected to prohibit or restrict the Company or any of its Subsidiaries from, or otherwise materially adversely effect the Company or any of its Subsidiaries in, conducting its business in any jurisdiction in which it now conducts its business.

3.7 Capitalization.

(a) (i) As of the Initial Closing Date, the authorized capital stock of the Company shall consist of (A) 200,000,000 shares of Common Stock, of which 23,025,902 shares are outstanding, (B) one share of Special Voting Stock, par value $0.001 per share, of the Company (C) 4,188,587 shares of Series D Preferred Stock, of which 4,102,355 shares are outstanding, (E) 68,000,000 shares of Series E Preferred Stock, of which 55,894,801 shares are outstanding, (F) 450,000 shares of Series F Preferred Stock, 385,710 of which shall be reserved for issuance upon exercise of the Warrants, and (G) 2,286,412 shares of undesignated “blank check” preferred stock. As of the date of this Agreement, the aggregate number of shares of restricted stock and options to purchase shares of Common Stock which may be issued under the Stock Option Plans are 18,745,440, of which 17,427,864 have been granted. The Company has reserved an adequate number of shares of Common Stock for issuance upon conversion of the Series F Preferred Stock.

(ii) As of the Second Closing Date, the authorized capital stock of the Company shall consist of (A) 200,000,000 shares of Common Stock, (B) one share of Special Voting Stock, par value $0.001 per share, of the Company, (C) 4,188,587 shares of Series D Preferred Stock, of which 4,102,355 shares shall be outstanding, except that the number of shares of Series D Preferred Stock outstanding may decrease due to the conversion of such shares to Common Stock, (E) 68,000,000 shares of Series E Preferred Stock, of which 55,894,801 shares shall be outstanding, (F) 450,000 of shares of Series F Preferred Stock,

13

385,710 of which shall be reserved for issuance upon exercise of the Warrants, except that the number of shares of Series E Preferred Stock outstanding may decrease due to the conversion of such shares to Common Stock, and (G) 2,286,412 shares of undesignated blank check” preferred stock.

(iii) Except as set forth on Schedule 3.7(a) and except for the Warrants and the Common Stock Warrants, there are no options, warrants, conversion privileges, subscription or purchase rights or other rights presently outstanding to purchase or otherwise acquire (A) any authorized but unissued, unauthorized or treasury shares of the Company’s capital stock, (B) any Stock Equivalents or (C) any other securities of the Company and there are no commitments, contracts, agreements, arrangements or understandings to which the Company is a party to issue any shares of the Company’s capital stock or any Stock Equivalents or other securities of the Company.

(b) Effective as of not later than the Initial Closing Date and the Second Closing Date, the Notes and Warrants to be issued at the First Closing and the Second Closing, respectively, shall be duly authorized, and assuming the accuracy of the representations and warranties of the Investors set forth in Article IV of this Agreement, will be issued in compliance with the registration and qualification requirements of all applicable federal, state and foreign securities laws and will be free and clear of all other Liens.

(c) Effective as of not later than the Initial Closing Date and the Second Closing Date, the Series F Preferred Stock issuable upon exercise of the Warrants issued at the First Closing and the Warrants issued at the Second Closing, respectively, and the shares of Common Stock issuable upon conversion of such Series F Preferred Stock, respectively, shall in each case be duly authorized and duly reserved for issuance, and when issued and delivered to the Investors, will be validly issued, fully paid and non-assessable, not be subject to any preemptive right or similar rights that have not been satisfied and assuming the accuracy of the representations and warranties of the Investors set forth in Article IV of this Agreement, will be issued in compliance with the registration and qualification requirements of all applicable federal, state and foreign securities laws and will be free and clear of all other Liens. None of the issued and outstanding shares of Common Stock were issued in violation of any preemptive rights.

3.8 No Default or Breach; Contractual Obligations. All of the Contractual Obligations to which the Company or any of its Subsidiaries is a party, whether written or oral, which are required by the Exchange Act to be disclosed in the SEC Reports (collectively, “Material Contractual Obligations”) are valid, subsisting, in full force and effect and binding upon the Company or its Subsidiary, as the case may be, and the other parties thereto, and the Company or its Subsidiary, as the case may be, has paid in full or accrued all amounts due thereunder and has satisfied in full or provided for all of its liabilities and obligations thereunder, except for such amounts as are being contested by the Company in good faith. Neither the Company nor any of its Subsidiaries has received notice of a default and is not in default under, or with respect to, any Material Contractual Obligation nor, to the Knowledge of the Company, does any

14

condition exist that with notice or lapse of time or both would constitute a default thereunder. To the Knowledge of the Company, no other party to any such Contractual Obligation is in default thereunder, nor does any condition exist that with notice or lapse of time or both would constitute a default by such other party thereunder.

3.9 Title to Properties. The Company and each of its Subsidiaries has good, record and marketable title in fee simple to, or holds interests as lessee under leases in full force and effect in, all real property used in connection with its business or otherwise owned or leased by it. The Company and each of its Subsidiaries owns and has good, valid and marketable title to all of its properties and assets used in its business or reflected as owned on the Financial Statements, in each case free and clear of all Liens, except for Permitted Liens, or that would required to be described in the notes to the Financial Statements.

3.10 Reports; Financial Statements. As of the respective dates of their filing with the Commission, all reports, registration statements and other filings, together with any amendments thereto, filed by the Company with the Commission since June 30, 2000 (the “SEC Reports”), complied in all material respects with the applicable requirements of the Securities Act, the Exchange Act, and the rules and regulations of the Commission promulgated thereunder, except as disclosed in the SEC Reports. The SEC Reports did not at the time they were filed with the Commission, or will not at the time they are filed with the Commission, contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary in order to make the statements therein, in the light of the circumstances under which they are made, not misleading. The Company has delivered or made available to the Investors true and complete copies of, or will make available at each Investor’s request the SEC Reports and any exhibits thereto. Except as set forth in Schedule 3.10(a), the Company is not aware of any issues raised by the Commission with respect to any of the SEC Reports, other than those disclosed in the SEC Reports.

(a) The consolidated financial statements (including, in each case, any related schedules or notes thereto) contained in or incorporated by reference in the SEC Reports and any such reports, registration statements and other filings to be filed by the Company with the Commission prior to the Initial Closing Date or the Second Closing Date, as the case may be (the “Financial Statements”), (i) have been or will be prepared in accordance with the published rules and regulations of the Commission and GAAP consistently applied during the periods involved (except as may be indicated in the notes thereto) and (ii) fairly present or will fairly present in all material respects the consolidated financial position of the Company and its Subsidiaries as of the respective dates thereof and the consolidated results of operations, statements of stockholders’ equity and cash flows for the periods indicated, except that any unaudited interim financial statements were or will be subject to normal and recurring year-end adjustments and may omit footnote disclosure as permitted by regulations of the Commission.

3.11 Taxes. (a) The Company and each of its Subsidiaries has paid all Taxes which have come due and are required to be paid by it through the date hereof, and all deficiencies or other additions to Tax, interest and penalties owed by it in connection

15

with any such Taxes, other than Taxes being disputed by the Company in good faith for which adequate reserves have been made in accordance with GAAP; (b) the Company and each of its Subsidiaries has timely filed or caused to be filed all returns for Taxes that it is required to file on and through the date hereof (including all applicable extensions), and all such Tax returns are accurate and complete in all material respects; (c) with respect to all Tax returns of the Company and each of its Subsidiaries, (i) there is no unassessed Tax deficiency proposed or, to the Knowledge of the Company, threatened against the Company or any of its Subsidiaries and (ii) no audit is in progress with respect to any return for Taxes, no extension of time is in force with respect to any date on which any return for Taxes was or is to be filed and no waiver or agreement is in force for the extension of time for the assessment or payment of any Tax; (d) all provisions for Tax liabilities of the Company and each of its Subsidiaries have been disclosed in the Financial Statements and made in accordance with GAAP consistently applied, and all liabilities for Taxes of the Company and each of its Subsidiaries attributable to periods prior to or ending on the Initial Closing Date or the Second Closing Date, as the case may be, have been adequately disclosed in the Financial Statements; and (e) there are no Liens for Taxes on the assets of the Company or any of its Subsidiaries, other than Permitted Liens.

3.12 No Material Adverse Change; Ordinary Course of Business. Except as set forth on Schedule 3.12, since December 31, 2003, (a) there has not been any material adverse change in the Condition of the Company, (b) neither the Company nor any of its Subsidiaries has participated in any transaction material to the Condition of the Company, including, without limitation, declaring or paying any dividend or declaring or making any distribution to its stockholders except out of the earnings of the Company or its Subsidiary, as the case may be, (c) neither the Company nor any of its Subsidiaries has entered into any Material Contractual Obligation, other than in the ordinary course of business and (d) there has not occurred a material change in the accounting principles or practice of the Company or any of its Subsidiaries except as required by reason of a change in GAAP.

3.13 Private Offering. Neither the Company nor any authorized Person acting on its behalf has, in connection with the offer, sale, exchange or issuance of the Notes, the Warrants, the Warrant Shares or the Common Shares, engaged in (a) any form of general solicitation or general advertising (as those terms are used within the meaning of Rule 502(c) under the Securities Act), (b) any action involving a public offering within the meaning of Section 4(2) of the Securities Act, or (c) any action that would require the registration under the Securities Act of the offering, sale, exchange or issuance of the Notes, the Warrants, the Series F Preferred Shares and the Common Shares pursuant to this Agreement or that would violate applicable state securities or “blue sky” laws. As used herein, the terms “offer” and “sale” have the meanings specified in Section 2(3) of the Securities Act.

3.14 Labor Relations . Except as could not reasonably be expected to have a material adverse effect on the Condition of the Company: (a) neither the Company nor any of its Subsidiaries is engaged in any unfair labor practice; (b) there is no strike, labor dispute, slowdown or stoppage pending or, to the Knowledge of the

16

Company, threatened against the Company or any of its Subsidiaries; (c) neither the Company nor any of its Subsidiaries is a party to any collective bargaining agreement or contract; and (d) no union organizing activities are taking place. To the Knowledge of the Company, no officer or key employee, or any group of key employees, intends to terminate their employment with the Company or any of its Subsidiaries. To the Knowledge of the Company, each of the officers and key employees of the Company and each of its Subsidiaries spends all, or substantially all, of his business time on the business of the Company or its Subsidiary, as the case may be. To the Knowledge of the Company, none of the employees of the Company or any of its Subsidiaries is resident in the United States in violation of any Requirement of Law.

3.15 Employee Benefit Plans.

(a) The SEC Reports list or describe each Plan that the Company or any of its Subsidiaries maintains or to which the Company or any of its Subsidiaries contributes (the “Company Plans”). Neither the Company nor any of its Subsidiaries has any liability under any Plans other than the Company Plans. Except as described in or incorporated by reference in the SEC Reports, neither the Company nor any Commonly Controlled Entity maintains or contributes to, or has within the preceding six years maintained or contributed to, or may have any liability with respect to any Plan subject to Title IV of ERISA or Section 412 of the Code or any “multiple employer plan” within the meaning of the Code or ERISA. Each Company Plan (and related trust, insurance contract or fund) has been established and administered in accordance with its terms, and complies in form and in operation with the applicable requirements of ERISA and the Code and other applicable Requirements of Law. All contributions (including all employer contributions and employee salary reduction contributions) which are due have been paid to each Company Plan.

(b) No Claim with respect to the administration or the investment of the assets of any Company Plan (other than routine claims for benefits) is pending.

(c) Except as could not reasonably be expected to have a material adverse effect on the Condition of the Company, each Company Plan that is intended to be qualified under Section 401(a) of the Code is so qualified and has been so qualified during the period since its adoption; each trust created under any such Plan is exempt from tax under Section 501(a) of the Code and has been so exempt since its creation.

(d) No Company Plan is a Retiree Welfare Plan.

(e) Neither the consummation of the transactions contemplated by this Agreement nor any termination of employment following such transactions will accelerate the time of the payment or vesting of, or increase the amount of, compensation due to any employee or former employee whether or not such payment would constitute an “excess parachute payment” under Section 280G of the Code.

(f) There are no unfunded obligations under any Company Plan which are not fully reflected in the Financial Statements.

17

(g) Except as could not reasonably be expected to have a material adverse effect on the Condition of the Company, the Company has no liability, whether absolute or contingent, including any obligations under any Company Plan, with respect to any misclassification of any person as an independent contractor rather than as an employee.

3.16 Liabilities. Neither the Company nor any of its Subsidiaries has any direct or indirect obligation or liability (the “Liabilities”) which are not fully reflected or reserved against in the Financial Statements, other than Liabilities not exceeding $1,000,000 in the aggregate incurred since December 31, 2003 in the ordinary course of business. The Company has no Knowledge of any circumstance, condition, event or arrangement that could reasonably be expected to give rise hereafter to any Liabilities of the Company or any of its Subsidiaries that, individually or in the aggregate, could have a material adverse effect on the Condition of the Company.

3.17 Affiliate Transactions. Except as set forth on Schedule 3.17, in the twelve (12) months preceding the date hereof, neither the Company nor any of its Subsidiaries has sold, leased or otherwise transferred any property or assets to, or purchased, leased or otherwise acquired any property or assets from, or otherwise engaged in any other transactions with, any of its Affiliates, except in (a) transactions that are at prices and on terms and conditions not less favorable to the Company or such Subsidiary than could be obtained on an arm’s length basis from unrelated third parties, (b) transactions exclusively between the Company and one or more of its Subsidiaries, or between two or more Subsidiaries of the Company, and which do not involve any other Affiliate and (c) transactions under the agreements listed on Schedule 3.17 hereto.

3.18 Intellectual Property.

(a) (i) The Company and each of its Subsidiaries is the owner of all, or has the license or right to use, sell and license all of, the Copyrights, Patents, Trade Secrets, Trademarks, Internet Assets, Software and other proprietary rights (collectively, “Intellectual Property”) that are used in connection with its business as presently conducted, free and clear of all Liens, other than Permitted Liens.

(ii) None of the Intellectual Property is subject to any outstanding Order, and no action, suit, proceeding, hearing, investigation, charge, complaint, claim or demand is pending or, to the Knowledge of the Company, threatened, which challenges the validity, enforceability, use or ownership of the item.

(iii) The Company and each of its Subsidiaries has substantially performed all obligations imposed upon it under all Intellectual Property licenses, sublicenses, distributor agreements and other agreements under which the Company or any of its Subsidiaries is either a licensor, licensee or distributor, except such licenses, sublicenses and other agreements relating to off-the-shelf

18

software which is commercially available on a retail basis and used solely on the computers of the Company or its Subsidiaries (collectively, the “IP Agreements”). The Company and each of its Subsidiaries is not, nor to the Knowledge of the Company is any other party thereto, in breach of or default thereunder in any respect, nor is there any event which with notice or lapse of time or both would constitute a default thereunder. All of the IP Agreements are valid, enforceable and in full force and effect, and will continue to be so on identical terms immediately following the Initial Closing and the Second Closing, as the case may be, except as enforceability may be limited by applicable bankruptcy, insolvency, reorganization, fraudulent conveyance or transfer, moratorium or similar laws affecting the enforcement of creditors’ rights generally and by general principles of equity relating to enforceability (regardless of whether considered in a proceeding at law or in equity).

(iv) None of the Intellectual Property currently sold or licensed by the Company or any of its Subsidiaries to any Person or used by or licensed to the Company or any of its Subsidiaries by any Person infringes upon or otherwise violates any Intellectual Property rights of others, except as could not reasonably be expected to have a material adverse effect on the Condition of the Company.

(b) No litigation is pending and no Claim has been made against the Company or any of its Subsidiaries or, to the Knowledge of the Company, is threatened, contesting the right of the Company or any of its Subsidiaries to sell or license to any Person or use the Intellectual Property presently sold or licensed to such Person or used by the Company or any of its Subsidiaries. To the Knowledge of the Company, no Person is infringing upon or otherwise violating the Intellectual Property rights of the Company or any of its Subsidiaries.

(c) No former employer of any employee of the Company or any of its Subsidiaries has made a claim against the Company or any of its Subsidiaries or, to the Knowledge of the Company, against any other Person, that such employee or such consultant is utilizing Intellectual Property of such former employer.

(d) To the Knowledge of the Company, none of the Trade Secrets, wherever located, the value of which is contingent upon maintenance of confidentiality thereof, has been disclosed to any Person other than employees, representatives and agents of the Company or any of its Subsidiaries, except as required pursuant to the filing of a patent application by the Company or any of its Subsidiaries.

(e) It is not necessary for the business of the Company or any of its Subsidiaries to use any Intellectual Property owned by any director, officer, employee or consultant of the Company or any of its Subsidiaries (or persons the Company or any of its Subsidiaries presently intends to hire). To the Company’s Knowledge, at no time during the conception or reduction to practice of any of the Intellectual Property of the Company or any of its Subsidiaries was any developer, inventor or other contributor to such Intellectual Property operating under any grants from any Governmental Authority or subject to any employment agreement, invention assignment, nondisclosure agreement

19

or other Contractual Obligation with any Person that could materially adversely affect the rights of the Company or any of its Subsidiaries to its Intellectual Property.

3.19 Privacy of Customer Information. Neither the Company nor any of its Subsidiaries use any of the customer information it receives through its website or otherwise in an unlawful manner, or in a manner violative of the privacy policy of the Company or its Subsidiary, as the case may be, or the privacy rights of its customers. Neither the Company nor any of its Subsidiaries has collected any customer information through its website in an unlawful manner or in violation of its privacy policy. The Company and each of its Subsidiaries has adequate security measures in place to protect the customer information it receives through its website and which it stores in its computer systems from illegal use by third parties or use by third parties in a manner violative of the rights of privacy of its customers. The Company and each of its Subsidiaries represents to its customers that it assures complete security as to the customer information it receives through its website.

3.20 Potential Conflicts of Interest. Except as set forth on Schedule 3.20, no officer, director or stockholder beneficially owning more than five percent (5%) of the outstanding shares of Common Stock, to the Knowledge of the Company, no spouse of any such officer, director or stockholder, and, to the Knowledge of the Company, no Affiliate of any of the foregoing (a) owns, directly or indirectly, any interest in (excepting less than one percent (1%) stock holdings for investment purposes in securities of publicly held and traded companies), or is an officer, director, employee or consultant of, any Person which is, or is engaged in business as, a competitor, lessor, lessee, supplier, distributor, or customer of, or Investor to or borrower from, the Company or any of its Subsidiaries; (b) owns, directly or indirectly, in whole or in part, any tangible or intangible property that the Company or any of its Subsidiaries use, in the conduct of business; or (c) has any cause of action or other claim whatsoever against, or owes or has advanced any amount to, the Company or any of its Subsidiaries, except for claims in the ordinary course of business such as for accrued vacation pay, accrued benefits under employee benefit plans, and similar matters and agreements existing on the date hereof.

3.21 Trade Relations. There exists no actual or, to the Knowledge of the Company, threatened termination, cancellation or limitation of, or any material adverse modification or change in, the business relationship of the Company or any of its Subsidiaries, or the business of the Company or any of its Subsidiaries, with any customer or supplier or any group of customers or suppliers whose purchases or inventories provided to the business of the Company or any of its Subsidiaries are individually or in the aggregate material to the Condition of the Company.

3.22 Outstanding Borrowing. Schedule 3.22 sets forth the amount of all Indebtedness of the Company and each of its Subsidiaries as of the date hereof, the Liens

20

that relate to such Indebtedness and that encumber the Assets and the name of each Investor thereof. No Indebtedness is entitled to any voting rights in any matters voted upon by the holders of the Common Stock.

3.23 Broker’s, Finder’s or Similar Fees. There are no brokerage commissions, finder’s fees or similar fees or commissions payable by the Company or any of its Subsidiaries in connection with the transactions contemplated hereby based on any agreement, arrangement or understanding with the Company or any of its Subsidiaries or any action taken by any such Person.

3.24 CCC Section. The provisions of Section 1203 of the California Corporations Code are not applicable to the transactions contemplated by this Agreement or any of the Transaction Documents.

3.25 Disclosure. This Agreement and the documents and certificates furnished to the Investors by the Company do not contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements contained herein or therein, in the light of the circumstances under which they were made, not misleading.

3.26 Investments. As of the date hereof, except as set forth on Schedule 3.26 hereto, neither the Company nor any of its Subsidiaries has made an Investment in any Person, other than a Permitted Investment.

3.27 Sarbanes-Oxley Compliance.

(a) The financial statements of the Company, together with the related schedules and notes, that are incorporated by reference in the Registration Statement and the Prospectus filed with the Commission on December 24, 2003, as amended: (i) present fairly, in all material respects, the financial position of the Company as of the dates indicated and the results of operations and cash flows of the Company for the periods specified; (ii) have been prepared in compliance with requirements of the Exchange Act and in conformity with generally accepted accounting principles in the United States applied on a consistent basis during the periods presented and the schedules included in the Registration Statement present fairly, in all material respects, the information required to be stated therein; and (iii) comply with the antifraud provisions of the Federal securities laws. There are no financial statements (historical or pro forma) that are required to be included in the Registration Statement and the Prospectus that are not included as required by the Securities Act. All non-GAAP financial measures included or incorporated by reference in the Registration Statement or the Prospectus comply in all material respects with the applicable requirements of the Sarbanes-Oxley Act of 2002 (the “Sarbanes-Oxley Act”) and the rules and regulations promulgated by the Commission thereunder.

(b) The Company’s Board of Directors has validly appointed an Audit Committee whose composition satisfies the requirements of Rule 4350A(d)(2) of the Rules of the National Association of Securities Dealers, Inc. (the “NASD Rules”) and the

21

Board of Directors and/or the Audit Committee has adopted a charter that satisfies the requirements of Rule 4350A(d)(1) of the NASD Rules.

(c) The Company has established and maintains disclosure controls and procedures (as such term is defined in Rule 13a-15 and 15d-15 under the Exchange Act). Such disclosure controls and procedures are designed to ensure that material information relating to the Company is made known to the Company’s principal executive officer and principal financial officer by others within the Company. As of the end of the Company’s last completed fiscal quarter, such disclosure controls and procedures were effective to perform the functions for which they were established, and the Company will use commercially reasonable efforts to ensure that the Company’s disclosure controls and procedures remain effective to perform the functions for which they were established. The Company’s auditors and the Audit Committee of the Board of Directors have been advised of: (i) any significant deficiencies and material weaknesses in the design or operation of internal controls over financial reporting which are reasonably likely to adversely affect the Company’s ability to record, process, summarize, and report financial information; and (ii) any fraud, whether or not material, that involves management or other employees who have a significant role in the Company’s internal controls over financial reporting. Since the date of the most recent evaluation of such disclosure controls and procedures, there have been no changes in internal controls over financial reporting that have materially affected, or are reasonably likely to materially affect, the Company’s internal control over financial reporting. The principal executive officer and the principal financial officers of the Company have made all certifications required by the Sarbanes-Oxley Act and any related rules and regulations promulgated by the Commission thereunder, and the statements contained in any such certification are complete and correct. The Company is in compliance in all material respects with all provisions of the Sarbanes-Oxley Act that are effective and applicable to the Company, except for the requirements of the Sarbanes-Oxley Act which are not yet required to be complied with by the Company. The Company has established procedures to implement timely additional rules and regulations applicable to the Company that may be promulgated by the Commission pursuant to the Sarbanes-Oxley Act.

ARTICLE IV

REPRESENTATIONS AND WARRANTIES OF THE

INVESTORS

Each of the Investors hereby represents and warrants, severally and not jointly, to the Company as follows:

4.1 Existence and Power. Such Investor (a) is a limited partnership, corporation, partnership or limited liability company duly organized and validly existing under the laws of the jurisdiction of its formation and (b) has the requisite partnership, corporate or limited liability company, as the case may be, power and authority to

22

execute, deliver and perform its obligations under this Agreement and each of the other Transaction Documents to which it is a party.

4.2 Authorization; No Contravention. The execution, delivery and performance by such Investor of this Agreement and each of the other Transaction Documents to which it is a party and the transactions contemplated hereby and thereby, (a) have been duly authorized by all necessary partnership, corporate or limited liability company, as the case may be, action, (b) do not contravene the terms of such Investor’s organizational documents, or any amendment thereof, (c) do not violate, conflict with or result in any breach or contravention of, or the creation of any Lien under, any Contractual Obligation of such Investor or any Requirement of Law applicable to such Investor, and (d) do not violate any Orders of any Governmental Authority against, or binding upon, such Investor.

4.3 Governmental Authorization; Third Party Consents. Except for the Stockholder Approval, no approval, consent, compliance, exemption, authorization or other action by, or notice to, or filing with, any Governmental Authority or any other Person, and no lapse of a waiting period under any Requirement of Law, is necessary or required in connection with the execution, delivery or performance by, or enforcement against, such Investor of this Agreement and each of the other Transaction Documents to which it is a party or the transactions contemplated hereby and thereby.

4.4 Binding Effect. This Agreement and each of the other Transaction Documents to which such Investor is a party, have been duly executed and delivered by such Investor, and this Agreement and each of the other Transaction Documents to which such Investor is a party, constitute the legal, valid and binding obligations of such Investor, enforceable against it in accordance with its terms, except as enforceability may be limited by applicable bankruptcy, insolvency, reorganization, fraudulent conveyance or transfer, moratorium or similar laws affecting the enforcement of creditors’ rights generally or by equitable principles relating to enforceability (regardless of whether considered in a proceeding at law or in equity).

4.5 Purchase for Own Account. The Notes, the Warrants and the Warrant Shares or Common Shares to be acquired by such Investor, respectively, are being or will be acquired for its own account and with no intention of distributing or reselling such Notes, Warrants, Warrant Shares or Common Shares or any part thereof in any transaction that would be in violation of the securities laws of the United States of America, any state of the United States or any foreign jurisdiction, without prejudice, however, to the rights of such Investor at all times to sell or otherwise dispose of all or any part of such Notes, Warrants, Warrant Shares and Common Shares under an effective registration statement under the Securities Act, or under an exemption from such registration available under the Securities Act, and subject, nevertheless, to the disposition of such Investor’s property being at all times within its control. If such Investor should in the future decide to dispose of any of such Notes, Warrants, Warrant Shares or Common Shares, such Investor understands and agrees that it may do so only in compliance with the Securities Act and applicable state and foreign securities laws, as then in effect. Such Investor agrees to the imprinting for so long as required by law, of a

23

legend on certificates representing all of its Notes, Warrants, Warrant Shares and Common Shares to the following effect:

THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE OF THE UNITED STATES OR ANY FOREIGN JURISDICTION. THE SECURITIES MAY NOT BE TRANSFERRED EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER SUCH ACT AND APPLICABLE STATE AND FOREIGN SECURITIES LAWS OR PURSUANT TO AN APPLICABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT AND SUCH LAWS.

4.6 Restricted Securities. Such Investor understands that the Notes, the Warrants, the Warrant Shares and Common Shares issuable upon exercise of the Warrants and conversion of the Series F Preferred Stock (the “Securities”) will not be registered at the time of their issuance under the Securities Act for the reason that the sale provided for in this Agreement is exempt pursuant to Section 4(2) of the Securities Act and that the reliance of the Company on such exemption is predicated in part on such Investor’s representations set forth herein.

4.7 Accredited Investor. Such Investor is an “Accredited Investor” within the meaning of Rule 501 of Regulation D under the Securities Act, as presently in effect.

4.8 Experience. Such Investor, either alone or together with its representatives, has such knowledge, sophistication and experience in business and financial matters so as to be capable of evaluating the merits and risks of the prospective investment in the Securities, and has so evaluated the merits and risks of such investment. Such Investor is able to bear the economic risk of an investment in the Securities and, at the present time, is able to afford a complete loss of such investment.

4.9 Access to Information. Such Investor has reviewed the SEC Reports and has been afforded: (a) the opportunity to ask such questions as it has deemed necessary of, and to receive answers from, representatives of the Company concerning the terms and conditions of the offering of the Securities and the merits and risks of investing in the Securities; (b) access to publicly available information about the Company and the Subsidiaries and the Condition of the Company sufficient to enable it to evaluate its investment; and (c) the opportunity to obtain such additional publicly

24

available information that the Company possesses or can acquire without unreasonable effort or expense that is necessary to make an informed investment decision with respect to the investment. Neither such inquiries nor any other investigation conducted by or on behalf of such Investor or its representatives or counsel shall modify, amend or affect such Investor’s right to rely on the truth, accuracy and completeness of the SEC Reports and the Company’s representations and warranties contained in the Transaction Documents.

4.10 General Solicitation. Such Investor is not purchasing the Securities as a result of any advertisement, article, notice or other communication regarding the Securities published in any newspaper, magazine or similar media or broadcast over television or radio or presented at any seminar or any other general solicitation or general advertisement.

4.11 Reliance. Such Investor understands and acknowledges that: (a) the Securities are being offered and sold to it without registration under the Securities Act in a private placement that is exempt from the registration provisions of the Securities Act and (b) the availability of such exemption depends in part on, and the Company will rely upon the accuracy and truthfulness of, the foregoing representations and such Investor hereby consents to such reliance.

ARTICLE V

CONDITIONS TO INITIAL CLOSING

5.1 Conditions to Investors’ Obligations. Each of the Investors’ obligation to consummate the transactions contemplated by the Initial Closing pursuant to this Agreement is subject to the fulfillment at or prior to the Initial Closing of the following conditions, any of which may be waived in whole or in part by such Investor:

(a) Representations and Warranties. The representations and warranties made by the Company in Article III hereof shall be true and correct on the Initial Closing Date.

(b) Performance. All covenants, agreements and conditions contained in this Agreement to be performed by the Company on or prior to the Initial Closing Date shall have been performed or complied with.

(c) Compliance Certificate. The Company shall have delivered to the Investors a certificate of the Company, executed by the Chief Executive Officer of the Company and dated as of the Initial Closing Date, certifying to the fulfillment of the conditions specified in Section 5.1(a) and Section 5.1(b) hereof.

25

(d) Secretary’s Certificate. The Company shall have delivered to the Investors a certificate from the Company, in form and substance satisfactory to the Investors, dated as of the Initial Closing Date and signed by the Secretary or an Assistant Secretary of the Company, certifying (i) that the Company is in good standing with the Secretary of State of the State of California and (ii) that the attached copies of the Articles of Incorporation, the By-laws, and resolutions of the Board of Directors of the Company approving this Agreement and each of the Transaction Documents to which the Company is a party and the transactions contemplated hereby and thereby, are all true, complete and correct and remain unamended and in full force and effect.

(e) Opinion of Counsel. The Company shall have caused the opinion of Paul, Hastings, Janofsky & Walker, LLP, dated the Initial Closing Date, relating to the transactions contemplated by the Initial Closing, substantially in the form attached hereto as Exhibit F to be delivered to the Investors.

(f) Transaction Documents. The Company shall have executed and delivered to the Investors each Transaction Document (other than this Agreement) to which it is a party.

(g) Compliance with Laws. The issuance of Notes and the Warrants at the Initial Closing pursuant to this Agreement and the Warrant Shares and Common Shares upon exercise of such Warrants and conversion of the Warrant Shares, respectively, pursuant to the terms of such Warrants, the Series F Certificate of Determination and this Agreement shall be legally permitted by all Requirements of Law to which the Company is subject.

(h) Qualifications. All authorizations, approvals, consents or permits, if any, of any Person that are required in connection with the lawful issuance and sale of the Notes and the Warrants at the Initial Closing pursuant to this Agreement and the Warrant Shares and Common Shares upon exercise of such Warrants and conversion of the Warrant Shares, respectively, pursuant to the terms of such Warrants, the Series F Certificate of Determination and this Agreement shall be duly obtained and effective as of the Initial Closing Date.

(i) Certificate of Determination. The Company shall have duly filed with the Secretary of State of the State of California the Series F Certificate of Determination.

(j) Deliveries. Simultaneously with the Initial Closing, the Company shall make the deliveries set forth in Section 2.4(c).

5.2 Conditions to Company’s Obligations. The Company’s obligation to consummate the transactions contemplated by the Initial Closing pursuant to this Agreement is subject to the fulfillment at or prior to the Initial Closing of the following conditions, any of which may be waived in whole or in part by the Company:

(a) Representations and Warranties. The representations and warranties made by the Investors in Article IV hereof shall be true and correct on the Initial Closing Date.

26

(b) Performance. All covenants, agreements and conditions contained in this Agreement to be performed by the Investors on or prior to the Initial Closing Date shall have been performed or complied with.

(c) Deliveries. Simultaneously with the Initial Closing, the Investors shall make the deliveries set forth in Section 2.4(d).

ARTICLE VI

CONDITIONS TO SECOND CLOSING

6.1 Conditions to Investors’ Obligations. Each of the Investors’ obligation to consummate the transactions contemplated by the Second Closing pursuant to this Agreement is subject to the fulfillment at or prior to the Second Closing of the following conditions, any of which may be waived in whole or in part by such Investor:

(a) Representations and Warranties. The representations and warranties made by the Company in Article III hereof shall be true and correct on the Second Closing Date.

(b) Performance. All covenants, agreements and conditions contained in this Agreement to be performed by the Company on or prior to the Second Closing Date shall have been performed or complied with.

(c) Compliance Certificate. The Company shall have delivered to the Investors a certificate of the Company, executed by the Chief Executive Officer of the Company and dated as of the Second Closing Date, certifying to the fulfillment of the conditions specified in Section 6.1(a) and Section 6.1(b) hereof.

(d) Secretary’s Certificate. The Company shall have delivered to the Investors a certificate from the Company, in form and substance satisfactory to the Investors, dated as of the Second Closing Date and signed by the Secretary or an Assistant Secretary of the Company, certifying (i) that the Company is in good standing with the Secretary of State of the State of California and (ii) that the attached copies of the Articles of Incorporation, the By-laws, and resolutions of the Board of Directors of the Company approving this Agreement and each of the Transaction Documents to which the Company is a party and the transactions contemplated hereby and thereby, are all true, complete and correct and remain unamended and in full force and effect.

(e) Opinion of Counsel. The Company shall have caused the opinion of Paul, Hastings, Janofsky & Walker, LLP, dated the Second Closing Date, relating to the transactions contemplated by the Second Closing, substantially in the form attached hereto as Exhibit F to be delivered to the Investors.

27

(f) Compliance with Laws. The issuance of Notes and the Warrants at the Second Closing pursuant to this Agreement and the Warrant Shares and Common Shares upon exercise of such Warrants and conversion of the Warrant Shares, respectively, pursuant to the terms of such Warrants, the Series F Certificate of Determination and this Agreement shall be legally permitted by all Requirements of Law to which the Company is subject.

(g) Qualifications. All authorizations, approvals, consents or permits, if any, of any Person that are required in connection with the lawful issuance and sale of the Notes and the Warrants at the Second Closing pursuant to this Agreement and the Warrant Shares and Common Shares upon exercise of such Warrants and conversion of the Warrant Shares, respectively, pursuant to the terms of such Warrants, the Series F Certificate of Determination and this Agreement shall be duly obtained and effective as of the Second Closing Date.

(h) Board Confirmation. The Company shall have sent written notice to the Investors after March 1, 2005, but on or prior to March 31, 2005, attaching a resolution or written consent approved by the non-interested members of the Board of Directors that states that it is in the best interests of the stockholders and creditors of the Company for the Company to borrow the aggregate principal amounts set forth opposite the Investors’ names on Schedule 2.1(b).

(i) Event of Default. There shall not be, or have been at any time since the First Closing, an Event of Default (as defined in the Notes) under the Notes issued to the Investors at the First Closing.

(j) Deliveries. Simultaneously with the Second Closing, the Company shall make the deliveries set forth in Section 2.4(e).

6.2 Conditions to Company’s Obligations. The Company’s obligation to consummate the transactions contemplated by the Second Closing pursuant to this Agreement is subject to the fulfillment at or prior to the Second Closing of the following conditions, any of which may be waived in whole or in part by the Company:

(a) Representations and Warranties. The representations and warranties made by the Investors in Article IV hereof shall be true and correct on the Second Closing Date.

(b) Performance. All covenants, agreements and conditions contained in this Agreement to be performed by the Investors on or prior to the Second Closing Date shall have been performed or complied with.

(c) Deliveries. Simultaneously with the Second Closing, the Investors shall make the deliveries set forth in Section 2.4(f).

28

ARTICLE VII

INDEMNIFICATION

7.1 Indemnification. Except as otherwise provided in this Article VII, the Company (the “Indemnifying Party”) agrees to indemnify, defend and hold harmless each of the Investors and their Affiliates and their respective officers, directors, agents, employees, subsidiaries, partners, members and controlling persons (each, an “Indemnified Party”) to the fullest extent permitted by law from and against any and all losses, Claims, or written threats thereof (including, without limitation, any Claim by a third party), damages, expenses (including reasonable fees, disbursements and other charges of counsel incurred by the Indemnified Party in any action between the Indemnifying Party and the Indemnified Party or between the Indemnified Party and any third party or otherwise) or other liabilities (collectively, “Losses”) resulting from or arising out of any breach of any representation or warranty, covenant or agreement by the Company in the Transaction Documents. The amount of any payment to any Indemnified Party herewith in respect of any Loss shall be of sufficient amount to make such Indemnified Party whole for any diminution in value of the Warrants, the Series F Preferred Stock, the Warrant Shares and/or Common Shares, as applicable, directly caused by such breach. In connection with the obligation of the Indemnifying Party to indemnify for expenses as set forth above, the Indemnifying Party shall, upon presentation of appropriate invoices containing reasonable detail, reimburse each Indemnified Party for all such expenses (including reasonable fees, disbursements and other charges of counsel incurred by the Indemnified Party in any action between the Indemnifying Party and the Indemnified Party or between the Indemnified Party and any third party) as they are incurred by such Indemnified Party; provided, however, that if an Indemnified Party is reimbursed under this Article VII for any expenses, such reimbursement of expenses shall be refunded to the extent it is finally judicially determined that the Losses in question resulted primarily from the willful misconduct or gross negligence of such Indemnified Party.

7.2 Notification. Each Indemnified Party under this Article VII shall, promptly after the receipt of notice of the commencement of any Claim against such Indemnified Party in respect of which indemnity may be sought from the Indemnifying Party under this Article VII, notify the Indemnifying Party in writing of the commencement thereof. The omission of any Indemnified Party to so notify the Indemnifying Party of any such action shall not relieve the Indemnifying Party from any liability which it may have to such Indemnified Party (a) other than pursuant to this Article VII or (b) under this Article VII unless, and only to the extent that, such omission results in the Indemnifying Party’s forfeiture of substantive rights or defenses. In case any such Claim shall be brought against any Indemnified Party, and it shall notify the Indemnifying Party of the commencement thereof, the Indemnifying Party shall be entitled to assume the defense thereof at its own expense, with counsel satisfactory to such Indemnified Party in its reasonable judgment; provided, however, that any Indemnified Party may, at its own expense, retain separate counsel to participate in such defense at its own expense. Notwithstanding the foregoing, in any Claim in which both the Indemnifying Party, on the one hand, and an Indemnified Party, on the other hand,

29

are, or are reasonably likely to become, a party, such Indemnified Party shall have the right to employ separate counsel and to control its own defense of such Claim if, in the reasonable opinion of counsel to such Indemnified Party, either (x) one or more defenses are available to the Indemnified Party that are not available to the Indemnifying Party or (y) a conflict or potential conflict exists between the Indemnifying Party, on the one hand, and such Indemnified Party, on the other hand, that would make such separate representation advisable; provided, however, that the Indemnifying Party (i) shall not be liable for the fees and expenses of more than one counsel to all Indemnified Parties and (ii) shall reimburse the Indemnified Parties for all of such fees and expenses of such counsel incurred in any action between the Indemnifying Party and the Indemnified Parties or between the Indemnified Parties and any third party, as such expenses are incurred; provided, however, that if an Indemnified Party is reimbursed under this Article VII for any expenses, such reimbursement of expenses shall be refunded to the extent it is finally judicially determined that the Losses in question resulted primarily from the willful misconduct or gross negligence of such Indemnified Party. The Indemnifying Party agrees that it will not, without the prior written consent of the Indemnified Party, settle, compromise or consent to the entry of any judgment in any pending or threatened Claim relating to the matters contemplated hereby (if any Indemnified Party is a party thereto or has been actually threatened to be made a party thereto) unless such settlement, compromise or consent includes an unconditional release of each Indemnified Party from all liability arising or that may arise out of such Claim. The Indemnifying Party shall not be liable for any settlement of any Claim effected against an Indemnified Party without the Indemnifying Party’s written consent, which consent shall not be unreasonably withheld. The rights accorded to an Indemnified Party hereunder shall be in addition to any rights that any Indemnified Party may have at common law, by separate agreement or otherwise; provided, however, that notwithstanding the foregoing or anything to the contrary contained in this Agreement, nothing in this Article VII shall restrict or limit any rights that any Indemnified Party may have to seek equitable relief.

7.3 Contribution. If the indemnification provided for in this Article VII from the Indemnifying Party is unavailable to an Indemnified Party hereunder in respect of any Losses referred to herein, then the Indemnifying Party, in lieu of indemnifying such Indemnified Party, shall contribute to the amount paid or payable by such Indemnified Party as a result of such Losses in such proportion as is appropriate to reflect the relative fault of the Indemnifying Party and Indemnified Party in connection with the actions which resulted in such Losses, as well as any other relevant equitable considerations. The relative faults of such Indemnifying Party and Indemnified Party shall be determined by reference to, among other things, whether any action in question, including any untrue or alleged untrue statement of a material fact or omission or alleged omission to state a material fact, has been made by, or relates to information supplied by, such Indemnifying Party or Indemnified Party, and the parties’ relative intent, knowledge, access to information and opportunity to correct or prevent such action. The amount paid or payable by a party as a result of the Losses referred to above shall be deemed to include, subject to the limitations set forth in Section 7.1 and Section 7.2, any reasonable legal or other fees, charges or expenses reasonably incurred by such party in connection with any investigation or proceeding.

30

ARTICLE VIII

COVENANTS

The Company hereby covenants and agrees with the Investors as follows:

8.1 Financial Statements and Other Information. If any time the Company is not subject to the periodic disclosure obligations of the Exchange Act, the Company shall deliver to each Investor, in form and substance satisfactory to such Investor:

(a) as soon as available, but not later than ninety (90) days after the end of each fiscal year of the Company, a copy of the audited consolidated balance sheet of the Company and its Subsidiaries as of the end of such fiscal year and the related statements of operations and cash flows for such fiscal year, setting forth in each case in comparative form the figures for the previous year, all in reasonable detail and accompanied by a management summary and analysis of the operations of the Company for such fiscal year and by the opinion of a nationally recognized independent certified public accounting firm which report shall state without qualification that such financial statements present fairly the financial condition as of such date and results of operations and cash flows for the periods indicated in conformity with GAAP applied on a consistent basis;

(b) as soon as available, but in any event not later than forty-five (45) days after the end of each of the first three fiscal quarters of each fiscal year, the unaudited consolidated balance sheet of the Company and its Subsidiaries, and the related statements of operations and cash flows for such quarter and for the period commencing on the first day of the fiscal year and ending on the last day of such quarter, all certified by an appropriate officer of the Company as presenting fairly the consolidated financial condition as of such date and results of operations and cash flows for the periods indicated in conformity with GAAP applied on a consistent basis, subject to normal year-end adjustments and the absence of footnotes required by GAAP; and

(c) as soon as available, but in any event not later than ten (10) days after the end of each month of each fiscal year, the unaudited consolidated balance sheet of the Company and its Subsidiaries, and the related statements of operations and cash flows for such month and for the period commencing on the first day of the fiscal year and ending on the last day of such month, all certified by an appropriate officer of the Company as presenting fairly the consolidated financial condition as of such date and results of operations and cash flows for the periods indicated in conformity with GAAP applied on a consistent basis, subject to normal year-end adjustments and the absence of footnotes required by GAAP.

8.2 FIRPTA Certificate. If requested by any of the Investors, as promptly as practicable, but not later than five (5) days after the end of each fiscal year of the Company, the Company shall deliver to such Investor, in form and substance satisfactory to such Investor, a certificate signed by the Chief Executive Officer of the

31

Company in customary form certifying that the Company is not a “foreign person” within the meaning of Section 1445 of the Code.

8.3 Reservation of Series F Preferred Stock and Common Stock. The Company shall at all times reserve and keep available out of its authorized shares of Series F Preferred Stock, solely for the purpose of issue or delivery upon exercise of the Warrants, as provided therein, the maximum number of shares of Series F Preferred Stock that may be issuable or deliverable upon such exercise. The Company shall at all times reserve and keep available out of its authorized shares of Common Stock, solely for the purpose of issue or delivery upon conversion of the Series F Preferred Stock, as provided in the Series F Certificate of Determination, the maximum number of shares of Common Stock that may be issuable or deliverable upon such conversion. The Company shall issue such shares of Series F Preferred Stock and Common Stock, in accordance with the terms of the Warrants and Series F Certificate of Determination, as the case may be, and otherwise comply with the terms hereof and thereof.

ARTICLE IX

TERMINATION

9.1 Termination. Sections 2.4(b), 2.4(e) and 2.4(f) of this Agreement and the obligation of the Investors to consummate the Second Closing shall automatically terminate and be of no further force or effect:

(a) at any time on or prior to the Second Closing Date, by mutual written consent of the Company and the Investors;

(b) at the election of the Company or the Investors by written notice to the other parties hereto after 5:00 p.m., New York time, on March 31, 2005, if the Second Closing shall not have occurred through no fault of the terminating party on or prior to such date, unless such date is extended by the mutual written consent of the Company and the Investors;

(c) at the election of the Company or any of the non-defaulting Investors, if there has been a material breach of any representation, warranty, covenant or agreement on the part of either of the General Atlantic Entities or Campina contained in this Agreement or the other Transaction Documents, which breach has not been cured within ten (10) Business Days of notice to the Investors of such breach; or

(d) at the election of any of the Investors, if there has been a material breach of any representation, warranty, covenant or agreement on the part of the Company contained in this Agreement or the other Transaction Documents, which breach has not been cured within ten (10) Business Days notice to the Company of such breach.

None of the parties hereto shall have any liability arising out of a termination pursuant to this Section 9.1.

32

ARTICLE X

MISCELLANEOUS

10.1 Survival of Representations and Warranties. All of the representations and warranties made herein shall survive the execution and delivery of this Agreement until the date that is ninety (90) days after the receipt by the Investors of audited financial statements of the Company for the fiscal year ending December 31, 2004 (or, if such fiscal year changes and no such audited consolidated financial statements are available, then the successor fiscal year), except for (a) Sections 3.1, 3.2, 3.4, 3.7, 3.13 and 3.23, which representations and warranties shall survive until the third anniversary of the Initial Closing Date, and (b) Section 3.11, which shall survive until the later to occur of (i) the lapse of the statute of limitations with respect to the assessment of any Tax to which such representation and warranty relates (including any extensions or waivers thereof) and (ii) sixty (60) days after the final administrative or judicial determination of the Taxes to which such representation and warranty relates, and no claim with respect to Section 3.11 may be asserted thereafter with the exception of claims arising out of any fact, circumstance, action or proceeding to which the party asserting such claim shall have given notice to the other parties to this Agreement prior to the termination of such period of reasonable belief that a tax liability will subsequently arise therefrom.

10.2 Notices. All notices, demands and other communications provided for or permitted hereunder shall be made in writing and shall be by registered or certified first-class mail, return receipt requested, telecopier, courier service or personal delivery:

if to the Company:

Critical Path, Inc.

350 The Embarcadero

San Francisco, CA 94105

Telecopy: (415) 541-2300

Attention: Chief Financial Officer

with a copy to, which shall not constitute notice to the Company:

Paul, Hastings, Janofsky & Walker LLP

55 Second Street, 24th Floor

San Francisco, California 94105-3441

Telecopy: (415) 856-7100

Attention: Gregg Vignos, Esq.

33

if to the Investors:

if to any of the General Atlantic Entities:

c/o General Atlantic Service Corporation

3 Pickwick Plaza

Greenwich, CT 06830

Telecopy: (203) 622-8818

Attention: Matthew Nimetz

Thomas J. Murphy

with a copy to, which shall not constitute notice:

Paul, Weiss, Rifkind, Wharton & Garrison LLP

1285 Avenue of the Americas

New York, NY 10019-6064

Telecopy: (212) 757-3990

Attention: Douglas A. Cifu, Esq.

if to Campina Enterprises Limited:

c/o 7th Floor

Cheung Kong Center

2 Queen’s Road Central

Hong Kong

Telecopy: (852) 2845-2057

Attention: Mr. Edmond Ip

(iv) if to Richmond III, LLC:

Richmond III, LLC

10563 Brunswick Road, Suite 7

Grass Valley, CA 95945

Telecopy: 530-272-0556

Attention: Peter Kellner

All such notices, demands and other communications shall be deemed to have been duly given when delivered by hand, if personally delivered; when delivered by courier, if delivered by commercial courier service; five (5) Business Days after being deposited in the mail, postage prepaid, if mailed; and when receipt is mechanically acknowledged, if telecopied. Any party may by notice given in accordance with this Section 10.2 designate another address or Person for receipt of notices hereunder.

34

10.3 Successors and Assigns; Third Party Beneficiaries. This Agreement shall inure to the benefit of and be binding upon the successors and permitted assigns of the parties hereto. Subject to applicable securities laws and the terms and conditions thereof, the Investors may assign any of their rights under this Agreement to any of their respective Affiliates. The Company may not assign any of its rights under this Agreement without the written consent of the Investors. Except as provided in Article VII, no Person other than the parties hereto and their successors and permitted assigns is intended to be a beneficiary of this Agreement.

10.4 Amendment and Waiver.

(a) No failure or delay on the part of the Company or the Investors in exercising any right, power or remedy hereunder shall operate as a waiver thereof, nor shall any single or partial exercise of any such right, power or remedy preclude any other or further exercise thereof or the exercise of any other right, power or remedy. The remedies provided for herein are cumulative and are not exclusive of any remedies that may be available to the Company or the Investors at law, in equity or otherwise.

(b) Any amendment, supplement or modification of or to any provision of this Agreement, any waiver of any provision of this Agreement, and any consent to any departure by the Company or the Investors from the terms of any provision of this Agreement, shall be effective (i) only if it is made or given in writing and signed by the Company and the Investors, and (ii) only in the specific instance and for the specific purpose for which made or given. Except where notice is specifically required by this Agreement, no notice to or demand on the Company in any case shall entitle the Company to any other or further notice or demand in similar or other circumstances.

(c) The Investors acknowledge and agree that notwithstanding the terms and provisions of this Agreement and the Notes, no Investor shall be entitled to take any action permitted to be taken by such Investor under this Agreement or the Notes unless such Investor holds, together with its Affiliates, Notes having an aggregate principal amount equal to at least 40% of the aggregate principal amount of all of the Notes issued at the Initial Closing and such Investor gives prompt written notice to the other Investors after such exercise or exercises.

10.5 Counterparts. This Agreement may be executed in any number of counterparts and by the parties hereto in separate counterparts, each of which when so executed shall be deemed to be an original and all of which taken together shall constitute one and the same agreement.

10.6 Richmond III Registration Rights. If a request for Incidental Registration (as defined in the Registration Rights Agreement) is made under the Registration Rights Agreement, and to the extent permitted by the Registration Rights Agreement, the Company agrees, upon the written request of Richmond III, to include shares of common stock issuable upon conversion of shares of Series F Preferred Stock

35

held by Richmond III in such Incidental Registration, as if Richmond III were a Designated Holder. The rights and obligations (including provision relating to registration expenses and indemnification and contribution) of a Designated Holder under the Registration Rights Agreement shall apply equally to the registration right granted to Richmond III under this Section to the extent applicable to effect the registration rights hereunder.

10.7 Coinvestor Sub-Group Board Seat. The Company covenants and agrees to cause the nomination of Mr. Edmond Ip Tak Chuen, as the nominee of the Coinvestor Sub-group (as defined in the Stockholders Agreement), to the Company’s Board of Directors at its next board meeting pursuant to its obligation under Section 3.1(b) of the Stockholders Agreement. The Company agrees to provide Mr. Edmond Ip Tak Chuen, so long as he is a member of the Company’s Board of Directors, copies of all materials which the Company provides to its Board of Directors. Such materials shall be sent to Mr. Edmond Ip Tak Chuen at the same time that they are sent to the Company’s Board of Directors.

10.8 Observer Rights. The Company covenants and agrees to allow one individual designated by the Coinvestor Sub-group (who shall initially be Mr. Ma Lai Chee) and one individual designated by General Atlantic Partners 74, L.P., (on behalf of General Atlantic Stockholders) (each, an “Observer”) to attend all meetings of the Company’s Board of Directors in a nonvoting capacity, and in connection therewith, the Company shall give each Observer copies of all materials which the Company provides to its Board of Directors, and such materials shall be sent to the Observers at the same time that they are sent to the Company’s Board of Directors; provided, however, that the Company reserves the right to exclude the Observers from access to any material or meeting or portion thereof if the Company believes upon advice of counsel that such exclusion is reasonably necessary to preserve the attorney-client privilege, to protect highly confidential information or for other similar reasons. The decision of the Board of Directors with respect to the privileged or confidential nature of such information shall be final and binding. Notice of meetings of the Company’s Board of Directors to the director nominated by the Coinvestor Sub-group and to the director nominated by the General Atlantic Stockholders (as defined in the Stockholders Agreement) shall constitute notice of such meetings to the Observers.

10.9 Certain Series F Preferred Stock Terms. The Company and the Investors agree as follows:

(a) The initial “Series F Conversion Price” (as defined in the Series F Certificate of Determination) is $1.40, as adjusted pursuant to Section 7(c) of the Series F Certificate of Determination;

(b) The initial “Series F Price Per Share” (as defined in the Series F Certificate of Determination) is $14.00 (subject to anti-dilution adjustment for stock splits

36

of, combinations of and capital reorganizations with respect to the Series F Preferred Stock); and

(c) The “Series F Closing Date” (as defined in the Series F Certificate of Determination) is December 30, 2004.

10.10 Headings. The headings in this Agreement are for convenience of reference only and shall not limit or otherwise affect the meaning hereof.

10.11 Governing Law. This Agreement shall be governed by and construed in accordance with the laws of the State of New York, without regard to the principles of conflicts of law thereof.

10.12 Severability. If any one or more of the provisions contained herein, or the application thereof in any circumstance, is held invalid, illegal or unenforceable in any respect for any reason, the validity, legality and enforceability of any such provision in every other respect and of the remaining provisions hereof shall not be in any way impaired, unless the provisions held invalid, illegal or unenforceable shall substantially impair the benefits of the remaining provisions hereof.

10.13 Rules of Construction. Unless the context otherwise requires, references to sections or subsections refer to sections or subsections of this Agreement.

10.14 Entire Agreement. This Agreement, together with the exhibits and schedules hereto, and the other Transaction Documents are intended by the parties as a final expression of their agreement and intended to be a complete and exclusive statement of the agreement and understanding of the parties hereto in respect of the subject matter contained herein and therein. There are no restrictions, promises, representations, warranties or undertakings, other than those set forth or referred to herein or therein. This Agreement, together with the exhibits and schedules hereto, and the other Transaction Documents supersede all prior agreements and understandings between the parties with respect to such subject matter.

10.15 Fees. In the event that the Investors fail to consummate the purchase of the Notes and the Warrants for any reason, the Company will not be responsible for any out-of-pocket fees and expenses incurred by the Investors. However, if the First Closing is consummated, the Company will reimburse the Investors for all of their reasonable out-of-pocket fees and expenses incurred in connection with the purchase of the Notes and Warrants, including fees and reasonable disbursements of counsel.

10.16 Publicity; Confidentiality. Except as may be required by applicable Requirements of Law, none of the parties hereto shall issue a publicity release or public announcement or otherwise make any disclosure concerning this Agreement, the transactions contemplated hereby, the Investors or the business, technology and financial affairs of the Company, without prior approval by the other parties hereto; provided, however, that nothing in this Agreement shall restrict any of the Investors from disclosing information (a) that is already publicly available, (b) that was known to such

37

Investor on a non-confidential basis prior to its disclosure by the Company, (c) that may be required or appropriate in response to any summons or subpoena or in connection with any litigation, provided that such Investor will use reasonable efforts to notify the Company in advance of such disclosure so as to permit the Company to seek a protective order or otherwise contest such disclosure, and such Investor will use reasonable efforts to cooperate, at the expense of the Company, with the Company in pursuing any such protective order, (d) to the extent that such Investor reasonably believes it appropriate in order to comply with any Requirement of Law, (e) to such Investor’s or the Company’s officers, directors, shareholders, advisors, employees, members, partners, controlling persons, auditors or counsel or (f) to Persons from whom releases, consents or approvals are required, or to whom notice is required to be provided, pursuant to the transactions contemplated by the Transaction Documents. If any announcement is required by any Requirement of Law to be made by any party hereto, prior to making such announcement such party will deliver a draft of such announcement to the other parties and shall give the other parties reasonable opportunity to comment thereon; provided, however, that the Investors may file an amendment to their Schedule 13D and Forms 4 with the Commission without either soliciting any comments from any of the other parties hereto or delivering a copy of such filings to any of the other parties hereto, except as required by law or regulation. Each of the Investors acknowledge that if such Investor becomes aware of material non-public information, such Investor’s ability to trade in the Company’s securities may be restricted.

10.17 Further Assurances. Each of the parties shall execute such documents and perform such further acts (including, without limitation, obtaining any consents, exemptions, authorizations or other actions by, or giving any notices to, or making any filings with, any Governmental Authority or any other Person) as may be reasonably required or desirable to carry out or to perform the provisions of this Agreement.

[the remainder of this page intentionally left blank]

38

IN WITNESS WHEREOF, the undersigned have executed, or have caused to be executed, this Note and Warrant Purchase Agreement on the date first written above.

	CRITICAL PATH, INC., a California corporation
By:	/s/ Michael Zukerman
Name:	Michael Zukerman
Title:	Executive Vice President, General Counsel and Secretary

Dated: December 29, 2004

SIGNATURE PAGE TO NOTE AND WARRANT PURCHASE AGREEMENT

	GENERAL ATLANTIC PARTNERS 74, L.P.
	By:	GENERAL ATLANTIC PARTNERS, LLC, its General Partner
By:	/s/ Matthew Nimetz
	Name:	Matthew Nimetz
	Title:	A Managing Member
	GAP COINVESTMENT PARTNERS II, L.P.
By:	/s/ Matthew Nimetz
	Name:	Matthew Nimetz
	Title:	A General Partner
	GAPSTAR, LLC
	By:	GENERAL ATLANTIC PARTNERS, LLC, its Sole Member
By:	/s/ Matthew Nimetz
	Name:	Matthew Nimetz
	Title:	A Managing Member
	GAPCO GMBH & CO. KG
	By:	GAPCO MANAGEMENT GMBH, its General Partner
By:	/s/ Matthew Nimetz
	Name:	Matthew Nimetz
	Title:	Managing Director

SIGNATURE PAGE TO NOTE AND WARRANT PURCHASE AGREEMENT

CAMPINA ENTERPRISES LIMITED
By:	/s/ Ma Lai Chee
	Name: Ma Lai Chee
	Title: Authorised Person

SIGNATURE PAGE TO NOTE AND WARRANT PURCHASE AGREEMENT

RICHMOND III, LLC
By:	/s/ Peter Kellner
	Name: Peter Kellner
	Title: Managing Member

SIGNATURE PAGE TO NOTE AND WARRANT PURCHASE AGREEMENT

SCHEDULE 2.1(a)

Initial Closing

Investors	Purchase Price		Principal Amount of Note		Shares of Series F Preferred Stock subject to Warrant
General Atlantic Partners 74, L.P.	$	4,146,663.81	$	4,146,663.81	88,857
GapStar, LLC	$	321,256.48	$	321,256.48	6,884
GAP Coinvestment Partners II, L.P.	$	523,982.98	$	523,982.98	11,228
GAPCO GmbH & Co. KG	$	8,096.73	$	8,096.73	173
Campina Enterprises Limited	$	5,000,000	$	5,000,000	107,142
Richmond III, LLC	$	1,000,000	$	1,000,000	21,428
Total:	$	11,000,000	$	11,000,000	235,712

SCHEDULE 2.1(b)

Second Closing

Investors	Purchase Price		Principal Amount of Note		Shares of Series F Preferred Stock subject to Warrant
General Atlantic Partners 74, L.P.	$	2,695,331.48	$	2,695,331.48	57,758
GapStar, LLC	$	208,816.71	$	208,816.71	4,474
GAP Coinvestment Partners II, L.P.	$	340,588.94	$	340,588.94	7,298
GAPCO GmbH & Co. KG	$	5,262.87	$	5,262.87	112
Campina Enterprises Limited	$	3,250,000	$	3,250,000	69,642
Richmond III, LLC	$	500,000	$	500,000	10,714
Total:	$	7,000,000	$	7,000,000	149,998