exv99w5

Exhibit 99.5

[Griffin Financial Group, LLC]

Dear Customer of Penn Millers Insurance Company:

At the request of Penn Millers Insurance Company and its affiliates, we have enclosed materials regarding the offering of common stock in connection with the conversion of Penn Millers Mutual Holding Company from a mutual holding company to a stock holding company. As part of this conversion, Penn Millers Mutual will form Penn Millers Holding Corporation, which will become the parent holding company of Penn Millers Mutual, and Penn Millers Mutual will become the stock holding company of Penn Millers Insurance Company. The enclosed materials include a prospectus and a stock order form, which offer you the opportunity to subscribe for shares of common stock of Penn Millers Holding Corporation. We are also enclosing a questions and answers brochure containing answers to commonly asked questions about the conversion and the offering.

Please read the prospectus carefully before making an investment decision. If you decide to subscribe for shares of common stock, you must return the properly completed and signed stock order form, along with full payment for the shares, to Penn Millers’ Stock Information Center in the accompanying postage-paid envelope marked “STOCK ORDER RETURN.” Your order must be physically received by the Stock Information Center no later than 12:00 noon, Eastern Time, on xxxxxx, xxxxxxxx xx, 2009. If you have any questions after reading the enclosed materials, please call the Stock Information Center at (877) 764-2743, Monday through Friday, between the hours of 10:00 a.m. and 4:00 p.m., and ask for a Griffin Financial representative.

We have been asked to forward these documents to you in view of certain requirements of the securities laws of your jurisdiction. We are not recommending or soliciting in any way any action by you with regard to the enclosed material.

Sincerely,

Griffin Financial Group, LLC

This letter is neither an offer to sell nor a solicitation of an offer to buy shares of common stock. The offer is made only by means of the Prospectus. No stock order forms shall be submitted or accepted until such time that our registration statement is effective with the U.S. Securities and Exchange Commission.

The shares of common stock are not insured and are not guaranteed by Penn Millers Holding Corporation or any of its affiliates or by any Federal or state government or agency.

[Griffin Financial Group Letterhead]

Dear Potential Investor:

At the request of Penn Millers Holding Corporation, we are enclosing materials regarding the offering of shares of common stock of Penn Millers Holding Corporation in connection with the conversion of Penn Millers Mutual Holding Company from mutual to stock form. Included in this package are the following:

PROSPECTUS: This document provides detailed information regarding the business operations of Penn Millers Insurance Company and the stock offering by Penn Millers Holding Corporation. Please read the Prospectus carefully, including the “Risk Factors” section, prior to making an investment decision.

QUESTIONS & ANSWERS BROCHURE: This brochure answers commonly asked questions about the conversion and offering.

STOCK ORDER FORM: Use this form to subscribe for common stock and mail it, along with full payment for the shares, to Penn Millers’ Stock Information Center in the enclosed postage-paid Order Reply Envelope. Your order must be physically received by the Stock Information Center no later than 12:00 noon, Eastern Time, on , 2009.

Griffin Financial Group, LLC has been retained by Penn Millers Holding Corporation as marketing agent in connection with the stock offering. If you have any questions after reading the enclosed materials, please call the Stock Information Center at 1 (877) 764-2743, Monday through Friday, between the hours of 10:00 a.m. and 4:00 p.m., and ask for a Griffin Financial representative. The Stock Information Center is closed on weekends and bank holidays.

Sincerely,

Griffin Financial Group, LLC

This letter is neither an offer to sell nor a solicitation of an offer to buy shares of common stock. The offer is made only by the Prospectus. No stock order forms shall be submitted or accepted until such time that our registration statement is effective with the U.S. Securities and Exchange Commission.

The shares of common stock are not insured and are not guaranteed by Penn Millers Holding Corporation or by any Federal or state government or agency.

[Penn Millers Mutual Holding Company]

Dear Member:

The Board of Directors of Penn Millers Mutual Holding Company has voted unanimously in favor of a plan to convert Penn Millers Mutual from a Pennsylvania mutual holding company to a Pennsylvania stock holding company. As part of this plan, we have formed Penn Millers Holding Corporation, which will be offering shares of its common stock in a stock offering and will become the parent holding company of Penn Millers Mutual. We are converting Penn Millers Mutual to stock form in order to raise additional capital that will enable Penn Millers Insurance Company to remain a viable, competitive and financially sound insurance company.

To accomplish the conversion, your participation is extremely important. A special meeting of eligible members of Penn Millers Mutual is being held on October 15, 2009. The members of Penn Millers Mutual consist of the policyholders of Penn Millers Insurance Company as of July 10, 2009. On behalf of the Board, I ask that you help us meet our goal by reading the enclosed material and then casting your vote in favor of the plan of conversion and mailing your signed proxy card immediately in the enclosed [COLOR] postage-paid envelope marked “PROXY RETURN.” Should you choose to attend the special meeting of the members and vote in person, you may do so by giving written notice of revocation to the Secretary of Penn Millers Mutual. If you have multiple insurance policies at Penn Millers Insurance Company, you may receive more than one mailing. If you do receive more than one proxy card, please vote, sign and return each one.

If the plan of conversion is approved, let me assure you that:

	•		Existing insurance coverage under your Penn Millers Insurance Company policy will not undergo any change as a result of the conversion.

	•		Voting for approval of the plan will not obligate you to buy any shares of common stock in the stock offering.

If you were a member of Penn Millers Mutual as of April 22, 2009, you may also take advantage of your nontransferable rights to subscribe for shares of Penn Millers Holding Corporation common stock on a first priority basis. The enclosed prospectus describes the stock offering and the business of Penn Millers. If you wish to purchase shares of common stock, please complete the stock order form and mail it, along with full payment for the shares to the Stock Information Center in the enclosed [COLOR] postage-paid Order Reply Envelope. Your order must be physically received by Stock Information Center no later than 12:00 noon, Eastern Time, on , 2009. Please read the prospectus carefully before making an investment decision.

If you have any questions after reading the enclosed material, please call our Stock Information Center at 1 (877) 764-2743, Monday through Friday, between the hours of 10:00 a.m. and 4:00 p.m.

Sincerely,

Douglas A. Gaudet
President and Chief Executive Officer

The shares of common stock are not insured and are not guaranteed by Penn Millers Holding Corporation, Penn Millers Insurance Company or by any Federal or state government or agency.

[Penn Millers Holding Corporation]

Dear Potential Investor/Friend:

I am pleased to tell you about an investment opportunity. In connection with the conversion of Penn Millers Mutual Holding Company from mutual to stock form, Penn Millers Holding Corporation, a newly formed company, will be conducting an initial public offering at a price per share of $10.00. Upon completion of the conversion and related stock offering, Penn Millers Holding Corporation will become the parent holding company of Penn Millers Mutual, and Penn Millers Holding Corporation will be owned by the persons who purchase shares in the offering. No sales commission will be charged to purchasers in this stock offering.

Before making an investment decision, please carefully review the enclosed Prospectus. If you are interested in purchasing shares of Penn Millers Holding Corporation common stock, complete the enclosed Stock Order Form and return it, with full payment, in the postage-paid Order Reply Envelope provided. If you wish to purchase stock with funds you have in an IRA, call our Stock Information Center promptly for guidance, because IRA-related orders require additional processing time. Stock Order Forms and full payment must be received (not postmarked) by 12:00 noon, Eastern Time, on , 2009, unless the offering is extended as described in the Prospectus.

If you have questions regarding the offering, please refer to the Prospectus and Q&A Brochure, or call our Stock Information Center at the number shown below.

Sincerely,

Douglas A. Gaudet
President and Chief Executive Officer

This letter is neither an offer to sell nor a solicitation of an offer to buy shares of common stock. The offer is made only by means of the Prospectus.

The shares of common stock are not insured and are not guaranteed by Penn Millers Holding Corporation, Penn Millers Insurance Company, or any of its affiliates or by any Federal or state government or agency.

QUESTIONS?

Call our Stock Information Center, toll free, at 1-877-764-2743
From 10:00 a.m. to 4:00 p.m., Eastern Time, Monday through Friday
The Stock Information Center is closed on weekends and bank holidays

Penn Millers Holding Corporation
Conversion and Stock Offering

Policyholder Considerations

As a policyholder of Penn Millers Insurance Company we are asking you to vote for our plan of mutual to stock conversion. We are also offering you the first chance to buy stock in the company if you want to do so.

The following are points to consider as you decide how to vote on the mutual to stock conversion of Penn Millers Mutual Holding Company and whether to purchase stock in the offering (along with references to the page numbers in the prospectus that you should read for a more complete description).

•

The conversion offering will provide enhanced protection to policyholders by:

	o		Increasing capital; and

	o		Enhancing claims paying ability (see pages 3-4, 7, 32, and 35-38 of the prospectus).

WE URGE YOU TO VOTE FOR THE PLAN OF CONVERSION.

	•		You are not required to purchase stock. But if you elect to do so, as a policyholder, you have the first right to purchase stock in the offering. This will permit you to own a share of the existing equity of the company (described throughout the prospectus).

	•		The stock is being offered at a pro forma price-to-book value of between 50% and 62% (see pages 43 and 116-119 of the prospectus).

We have filed a Registration Statement on Form S-1 (including a prospectus) with the SEC (Commission File No. 333-156936) for the offering to which this document relates. Before you invest, you should read the prospectus in the registration statement and other documents

we have filed with the SEC for more complete information about Penn Millers and this offering. If you have not already received a copy of these documents, you may get them for free by visiting EDGAR on the SEC web site at http://www.sec.gov. Alternatively, Penn Millers will arrange to send you a copy of the prospectus if you request it by calling the company toll-free at 1-800-233-8347.

Penn Millers Holding Corporation
Conversion and Stock Offering

Investment Considerations
for Potential Investors

The following are investment considerations for investors in our stock offering (along with references to the page numbers in our prospectus that you should read for a more complete description).

	•		The stock is being offered at a pro forma price-to-book value of between 50% and 62% (see pages 43 and 116-119 of the prospectus)

	•		We have a significant market position in the agribusiness insurance market, operating in 33 states. This is a specialized niche market with a limited number of competitors where we believe we have expertise and strong growth opportunities (see pages 2-5, 85-86, 89 and 102 of the prospectus).

	•		We also operate in the general commercial insurance market in eight states. We have developed a new product (PennEdge) that we introduced in 2009 to attract middle market commercial business. We believe this can be a differentiating product for us in a competitive market (see pages 2-5, 18, 84-85 and 87-88 of the prospectus).

	•		The property and casualty insurance industry is cyclical, with periods of rising and falling premiums known as hard and soft markets. The industry has been experiencing soft market conditions. Although no assurance can be given, we believe that a hard market with rising premiums will return in 2010 and 2011. We have historically performed well in periods of significant premium increases (see pages 3-4, 16-17 and 84 of the prospectus).

We have filed a Registration Statement on Form S-1 (including a prospectus) with the SEC (Commission File No. 333-156936) for the offering to which this document relates. Before you invest, you

should read the prospectus in the registration statement and other documents we have filed with the SEC for more complete information about Penn Millers and this offering. If you have not already received a copy of these documents, you may get them for free by visiting EDGAR on the SEC web site at http://www.sec.gov. Alternatively, Penn Millers will arrange to send you a copy of the prospectus if you request it by calling the company toll-free at 1-800-233-8347.