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<TITLE>FORM S-8</TITLE>
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<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>
<DIV style="font-family: 'Times New Roman',Times,serif">




<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>As filed with the Securities and Exchange Commission on May&nbsp;23, 2006</B>
</DIV>


<DIV align="right" style="font-size: 10pt; margin-top: 12pt"><B>Registration No.&nbsp;333-</B>
</DIV>


<DIV style="width: 100%; border-bottom: 2pt solid black; font-size: 1pt">&nbsp;</DIV>
<DIV style="width: 100%; border-bottom: 1pt solid black; font-size: 1pt">&nbsp;</DIV>




<DIV align="center" style="font-size: 14pt; margin-top: 12pt"><B>SECURITIES AND EXCHANGE COMMISSION</B>
</DIV>

<DIV align="center" style="font-size: 12pt"><B>Washington, D.C. 20549</B>
</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><DIV align="center"><DIV style="font-size: 3pt; margin-top: 16pt; width: 26%; border-top: 1px solid #000000">&nbsp;</DIV></DIV></DIV>

<DIV align="center" style="font-size: 18pt; margin-top: 12pt"><B>Form&nbsp;S-8</B>
</DIV>


<DIV align="center" style="font-size: 12pt; margin-top: 12pt"><B>REGISTRATION STATEMENT<BR>
UNDER<BR>
THE SECURITIES ACT OF 1933</B>
</DIV>

<DIV align="center" style="font-size: 24pt; margin-top: 12pt"><B>DARWIN PROFESSIONAL UNDERWRITERS, INC.</B>
</DIV>

<DIV align="center" style="font-size: 10pt">(Exact name of Registrant as specified in its charter)</DIV>


<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
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<TR valign="bottom">
    <TD align="center" valign="top"><B>Delaware</B>
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top"><B>03-0510450</B></TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top">(State or other jurisdiction of
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top">(I.R.S. Employer</TD>
</TR>
<TR valign="bottom">
    <TD align="center" valign="top">incorporation or organization)
</TD>
    <TD>&nbsp;</TD>
    <TD align="center" valign="top">Identification Number)</TD>
</TR>
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</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>9 Farm Springs Road<BR>
Farmington, Connecticut 06032<BR>
(860)&nbsp;284-1300</B><BR>
(Address of Principal Executive Offices) (Zip Code)</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><DIV align="center"><DIV style="font-size: 3pt; margin-top: 16pt; width: 26%; border-top: 1px solid #000000">&nbsp;</DIV></DIV></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><FONT style="border-bottom: 1px solid #000000"><B>Darwin
Professional Underwriters, Inc. 2006 Stock Incentive Plan</B></FONT><BR>
(Full title of the plan)</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><DIV align="center"><DIV style="font-size: 3pt; margin-top: 16pt; width: 26%; border-top: 1px solid #000000">&nbsp;</DIV></DIV></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>Stephen Sills<BR>
President and Chief Executive Officer<BR>
9 Farm Springs Road<BR>
Farmington, Connecticut 06032</B><BR>
(Name and address of agent for service)</DIV>


<DIV align="center" style="font-size: 12pt; margin-top: 12pt"><B><DIV align="center"><DIV style="font-size: 3pt; margin-top: 16pt; width: 26%; border-top: 1px solid #000000">&nbsp;</DIV></DIV></B>
</DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>Telephone number, including area code, of agent for service:<BR>
(860)&nbsp;284-1300</B></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 12pt"><B>CALCULATION OF REGISTRATION FEE</B></DIV>

<DIV align="center">
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    <TD width="1%">&nbsp;</TD>
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    <TD width="21%">&nbsp;</TD>
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    <TD width="2%">&nbsp;</TD>
    <TD width="12%">&nbsp;</TD>

    <TD width="1%">&nbsp;</TD>
</TR><TR style="font-size: 1px" valign="bottom">
    <TD nowrap align="left" colspan="15" style="border-bottom: 3px double #000000">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">    <TD width="1%">&nbsp;</TD>

    <TD>&nbsp;</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Proposed Maximum</B></TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Amount of</B></TD>
    <TD width="1%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">    <TD width="1%">&nbsp;</TD>

    <TD nowrap align="center"><B>Title of Each Class of</B></TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Proposed Maximum Offering Price Per</B></TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Aggregate Offering</B></TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Registration</B></TD>
    <TD width="1%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">    <TD width="1%">&nbsp;</TD>

    <TD nowrap align="center"><B>Securities to be Registered</B></TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Amount To Be Registered (1)</B></TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Share (2)</B></TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Price(2)</B></TD>
    <TD style="border-right: 2px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center"><B>Fee</B></TD>
    <TD width="1%">&nbsp;</TD>
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    <TD width="1%" style="border-top: 1px solid #000000">&nbsp;</TD>
                    <TD style="border-top: 1px solid #000000"><DIV style="margin-left:15px; text-indent:-15px">Common Stock, $0.01
par value per share</DIV></TD>
    <TD style="border-right: 2px solid #000000; border-top: 1px solid #000000">&nbsp;</TD>
    <TD style="border-top: 1px solid #000000">&nbsp;</TD>
    <TD align="center" valign="bottom" style="border-top: 1px solid #000000">850,000</TD>
    <TD style="border-right: 2px solid #000000; border-top: 1px solid #000000">&nbsp;</TD>
    <TD style="border-top: 1px solid #000000">&nbsp;</TD>
    <TD align="center" valign="bottom" style="border-top: 1px solid #000000">$18.55</TD>
    <TD style="border-right: 2px solid #000000; border-top: 1px solid #000000">&nbsp;</TD>
    <TD style="border-top: 1px solid #000000">&nbsp;</TD>
    <TD align="center" valign="bottom" style="border-top: 1px solid #000000">$15,767,500.00</TD>
    <TD style="border-right: 2px solid #000000; border-top: 1px solid #000000">&nbsp;</TD>
    <TD style="border-top: 1px solid #000000">&nbsp;</TD>
    <TD align="center" valign="bottom" style="border-top: 1px solid #000000">$1,687.12</TD>
    <TD width="1%" style="border-top: 1px solid #000000">&nbsp;</TD>
</TR>
<TR style="font-size: 1px" valign="bottom">
    <TD nowrap align="left" colspan="15" style="border-top: 3px double #000000">&nbsp;</TD>
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</DIV>

<DIV style="margin-top: 6pt">
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<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="1%" nowrap align="left">(1)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>Plus such additional shares as may be issued by reason of stock splits, stock dividends or
similar transactions.</TD>
</TR>

</TABLE>
</DIV>

<DIV style="margin-top: 3pt">
<TABLE width="100%" border="0" cellpadding="0" cellspacing="0" style="font-size: 10pt">

<TR valign="top" style="font-size: 10pt; color: #000000; background: transparent">
    <TD width="1%" nowrap align="left">(2)</TD>
    <TD width="1%">&nbsp;</TD>
    <TD>Pursuant to Rules 457(h) and 457(c), these prices are estimated solely for the purpose of
calculating the registration fee and are based upon the average of the high and low sales
prices of the Registrant&#146;s common stock on the NYSE Arca Exchange on May&nbsp;22, 2006.</TD>
</TR>

</TABLE>
</DIV>

<DIV style="width: 100%; border-bottom: 1pt solid black; margin-top: 10pt; font-size: 1pt">&nbsp;</DIV>
<DIV style="width: 100%; border-bottom: 2pt solid black; font-size: 1pt">&nbsp;</DIV>





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<DIV style="font-family: 'Times New Roman',Times,serif">
















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<A name="toc"><DIV align="CENTER" style="page-break-before:always"><U><B>TABLE OF CONTENTS</B></U></DIV></A>

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</TR>
<TR><TD colspan="9"><A HREF="#000">PART I</A></TD></TR>
<TR><TD colspan="9"><A HREF="#001">PART II</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#002">Item&nbsp;3. Incorporation of Documents by Reference</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#003">Item&nbsp;4. Description of Securities</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#004">Item&nbsp;5. Interests of Named Experts and Counsel</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#005">Item&nbsp;6. Indemnification of Directors and Officers</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#006">Item&nbsp;7. Exemption from Registration Claimed</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#007">Item&nbsp;8. Exhibits</A></TD></TR>
<TR><TD></TD><TD colspan="8"><A HREF="#008">Item&nbsp;9. Undertakings</A></TD></TR>
<TR><TD colspan="9"><A HREF="#009">SIGNATURES</A></TD></TR>
<TR><TD colspan="9"><A HREF="y21603aexv5w1.htm">EX-5.1: OPINION OF DEWEY BALLANTINE LLP</A></TD></TR>
<TR><TD colspan="9"><A HREF="y21603aexv10w1.txt">EX-10.1: STOCK INCENTIVE PLAN</A></TD></TR>
<TR><TD colspan="9"><A HREF="y21603aexv23w2.htm">EX-23.2: CONSENT OF KPMG LLP</A></TD></TR>
</TABLE>
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<!-- link1 "PART I" -->
<DIV align="left"><A NAME="000"></A></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>PART I</B>
</DIV>


<DIV align="Center" style="font-size: 10pt; margin-top: 12pt"><B>INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS</B>

</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The document(s) containing the information specified by Part&nbsp;I of this Form S-8 Registration
Statement (the &#147;Registration Statement&#148;) will be sent or given to participants in the plan listed
on the cover of this Registration Statement (the &#147;Plan&#148;) as specified by Rule&nbsp;428(b)(1) promulgated
by the Securities and Exchange Commission (the &#147;Commission&#148;) under the Securities Act of 1933, as
amended (the &#147;Securities Act&#148;). Such document(s) are not being filed with the Commission but
constitute (along with the documents incorporated by reference in this Registration Statement
pursuant to Item&nbsp;3 of Part&nbsp;II hereof) a prospectus that meets the requirements of Section 10(a) of
the Securities Act.
</DIV>
<!-- link1 "PART II" -->
<DIV align="left"><A NAME="001"></A></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>PART II</B>
</DIV>

<!-- link2 "Item&nbsp;3. Incorporation of Documents by Reference" -->
<DIV align="left"><A NAME="002"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;3. Incorporation of Documents by Reference.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The following documents filed with the Commission by the Registrant are incorporated herein by
reference and made a part hereof:
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)&nbsp;The Registrant&#146;s Prospectus filed with the Commission on May&nbsp;22, 2006 pursuant to rule
424(b) under the Securities Act;
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)&nbsp;The Registrant&#146;s Current Report on Form 8-K filed with the Commission on May&nbsp;23, 2006; and
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)&nbsp;The description of the Registrant&#146;s Common Stock in the Registrant&#146;s Registration
Statement on Form 8-A, File No.&nbsp;001-32883, filed with the Commission on May&nbsp;16, 2006 pursuant to
Section&nbsp;12 of the Securities Exchange Act of 1934, as amended (the &#147;Exchange Act&#148;), including any
further amendments or reports filed for the purpose of updating such description.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;All other documents subsequently filed by the Registrant pursuant to Sections&nbsp;13(a), 13(c), 14
and 15(d) of the Exchange Act prior to the filing of a post-effective amendment which indicates
that all securities offered hereunder have been sold or which deregisters all such securities then
remaining unsold shall be deemed to be incorporated by reference in this Registration Statement and
be a part hereof from the date of filing of such documents.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Any statement contained herein or in a document incorporated or deemed to be incorporated by
reference herein shall be deemed to be modified or superseded for purposes of this Registration
Statement to the extent that a statement contained herein or in any other subsequently filed
document which also is or is deemed to be incorporated by reference herein modifies or supersedes
such earlier statement. Any statement so modified or superseded shall not be deemed, except as so
modified or superseded, to constitute a part of this Registration Statement.
</DIV>
<!-- link2 "Item&nbsp;4. Description of Securities" -->
<DIV align="left"><A NAME="003"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;4. Description of Securities.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Not applicable.
</DIV>
<!-- link2 "Item&nbsp;5. Interests of Named Experts and Counsel" -->
<DIV align="left"><A NAME="004"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;5. Interests of Named Experts and Counsel.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Not applicable.
</DIV>
<!-- link2 "Item&nbsp;6. Indemnification of Directors and Officers" -->
<DIV align="left"><A NAME="005"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;6. Indemnification of Directors and Officers.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;145(a) of the General Corporation Law of the State of Delaware (the &#147;DGCL&#148;) provides
that a Delaware corporation may indemnify any person who was or is a party or is threatened to be
made a party to any threatened, pending or completed action, suit or proceeding, whether civil,
criminal, administrative or investigative (other than an action by or in the right of the
corporation) by reason of the fact that he is or was a director, officer, employee or agent of the
corporation or is or was serving at the request of the corporation as a director, officer, employee
or agent of another corporation or enterprise, against expenses, judgments, fines and amounts paid
in settlement actually and reasonably incurred by him in connection with such action, suit or
proceeding if he acted in good faith and in a manner he reasonably believed to be in or not opposed
to the best interests of the corporation, and, with respect to any criminal action or proceeding,
he had no cause to believe his conduct was unlawful.
</DIV>

<P align="center" style="font-size: 10pt">2
</DIV>

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<DIV style="font-family: 'Times New Roman',Times,serif">

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;145(b) of the DGCL provides that a Delaware corporation may indemnify any person who
was or is a party or is threatened to be made a party to any threatened, pending or completed
action or suit by or in the right of the corporation to procure a judgment in its favor by reason
of the fact that such person acted in any of the capacities set forth above, against expenses
actually and reasonably incurred by him in connection with the defense or settlement of such action
or suit if he acted under similar standards, except that no indemnification may be made in respect
of any claim, issue or matter as to which such person shall have been adjudged to be liable to the
corporation unless and only to the extent that the court in which such action or suit was brought
shall determine that despite the adjudication of liability, such person is fairly and reasonably
entitled to be indemnified for such expenses which the court shall deem proper.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;145 of the DGCL further provides that to the extent a director or officer of a
corporation has been successful in the defense of any action, suit or proceeding referred to in
subsections (a)&nbsp;and (b)&nbsp;or in the defense of any claim, issue, or matter therein, he shall be
indemnified against expenses (including attorneys&#146; fees) actually and reasonably incurred by him in
connection therewith; that indemnification provided for by Section&nbsp;145 shall not be deemed
exclusive of any other rights to which the indemnified party may be entitled; and that the
corporation may purchase and maintain insurance on behalf of a director or officer of the
corporation against any liability asserted against him or incurred by him in any such capacity or
arising out of his status as such whether or not the corporation would have the power to indemnify
him against such liabilities under such Section&nbsp;145.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Section&nbsp;102(b)(7) of the DGCL provides that a corporation in its original certificate of
incorporation or an amendment thereto validly approved by stockholders may eliminate or limit
personal liability of members of its board of directors or governing body for breach of a
director&#146;s fiduciary duty. However, no such provision may eliminate or limit the liability of a
director for breaching his duty of loyalty, failing to act in good faith, engaging in intentional
misconduct or knowingly violating a law, paying a dividend or approving a stock repurchase which
was illegal, or obtaining an improper personal benefit. A provision of this type has no effect on
the availability of equitable remedies, such as injunction or rescission, for breach of fiduciary
duty.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The Registrant&#146;s Certificate of Incorporation and By-Laws provide that the Registrant shall
indemnify officers, directors, employees and agents of the Registrant, to the full extent permitted
by and in the manner permissible under the laws of the State of Delaware. In addition, the
Certificate of Incorporation permits the board of directors to authorize the Registrant to purchase
and maintain insurance against any liability asserted against any director, officer, employee or
agent of the Registrant arising out of his capacity as such.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Alleghany Corporation maintains liability insurance for its directors and officers and for the
directors and officers of its majority-owned subsidiaries, including us. This insurance provides
for coverage, subject to certain exceptions, against loss from claims made against directors and
officers in their capacity as such, including claims under the federal securities laws.
</DIV>
<!-- link2 "Item&nbsp;7. Exemption from Registration Claimed" -->
<DIV align="left"><A NAME="006"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;7. Exemption from Registration Claimed.</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Not applicable.
</DIV>
<!-- link2 "Item&nbsp;8. Exhibits" -->
<DIV align="left"><A NAME="007"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;8. Exhibits.</B>
</DIV>

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
    <TD width="7%">&nbsp;</TD>
    <TD width="3%">&nbsp;</TD>
    <TD width="90%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">
    <TD nowrap align="center">Exhibit</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">
    <TD nowrap align="center">Number</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Description</TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR style="font-size: 1px">
    <TD colspan="3" valign="top" align="left" style="border-top: 1px solid #000000">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">3.1.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Certificate of Incorporation of the Registrant. (Incorporated by reference to Exhibit&nbsp;3.1.1 of the Registrant&#146;s
Registration Statement on Form&nbsp;S-1, as amended, File No.&nbsp;333-132355).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">3.1.2
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Certificate of Amendment to Certificate of Incorporation of the Registrant dated November&nbsp;30, 2005. (Incorporated
by reference to Exhibit&nbsp;3.1.2 of the Registrant&#146;s Registration Statement on Form&nbsp;S-1, as amended, File No.
333-132355).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">3.1.3
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Certificate of Amendment to Certificate of Incorporation of the Registrant dated May&nbsp;15, 2006. (Incorporated by
reference to Exhibit&nbsp;3.1.3 of the Registrant&#146;s Registration Statement on Form&nbsp;S-1, as amended, File No.
333-132355).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">3.1.4
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Form of Amended and Restated Certificate of Incorporation (to be effective upon the completion of the
Registrant&#146;s initial public offering). (Incorporated by reference to Exhibit&nbsp;3.1.4 of the Registrant&#146;s
Registration Statement on Form&nbsp;S-1, as amended, File No.&nbsp;333-132355).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">3.2
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Amended and Restated By-laws. (Incorporated by reference to Exhibit&nbsp;3.2 of the Registrant&#146;s Registration
Statement on Form&nbsp;S-1, as amended, File No.&nbsp;333-1323556).</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>


<P align="center" style="font-size: 10pt">3
</DIV>

<!-- PAGEBREAK -->
<P><HR noshade><P>
<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>
<DIV style="font-family: 'Times New Roman',Times,serif">

<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
    <TD width="7%">&nbsp;</TD>
    <TD width="3%">&nbsp;</TD>
    <TD width="90%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">
    <TD nowrap align="center">Exhibit</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">
    <TD nowrap align="center">Number</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="center">Description</TD>
</TR>
<TR style="font-size: 1px">
    <TD colspan="3" valign="top" align="left" style="border-top: 1px solid #000000">&nbsp;</TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">4.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Specimen Stock Certificate. (Incorporated by reference to Exhibit&nbsp;4.1 of the Registrant&#146;s Registration Statement
on Form&nbsp;S-1, as amended, File No.&nbsp;333-1323556).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">4.2
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Registration Rights Agreement by and between the Registrant and Alleghany Insurance Holdings LLC. (Incorporated
by reference to Exhibit&nbsp;4.1 of the Registrant&#146;s current report on Form&nbsp;8-K filed with the Commission on May&nbsp;23,
2006).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">4.3
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Master Agreement by and between the Registrant and Alleghany Corporation. (Incorporated by reference to Exhibit
4.2 of the Registrant&#146;s current report on Form&nbsp;8-K filed with the Commission on May&nbsp;23, 2006).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">5.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Opinion of Dewey Ballantine LLP will respect to the legality of the securities being registered. (Filed herewith).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">10.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Darwin Professional Underwriters,
Inc. 2006 Stock Incentive Plan. (Filed herewith).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">23.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Consent of Dewey Ballantine LLP. (Included in Exhibit&nbsp;5.1 hereto).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">23.2
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Consent of KPMG LLP. (Filed herewith).</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">24.1
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Power of Attorney of directors and
certain officers of the Registrant. (Included on Signature Page).</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>

<!-- link2 "Item&nbsp;9. Undertakings" -->
<DIV align="left"><A NAME="008"></A></DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 12pt"><B>Item&nbsp;9. Undertakings.</B>
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">(a)&nbsp;The undersigned Registrant hereby undertakes:
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">(1)&nbsp;To file, during any period in which offers or sales are being made, a post-effective amendment
to this Registration Statement:
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(i)&nbsp;To include any prospectus required by Section&nbsp;10(a)(3) of the Securities Act;
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(ii)&nbsp;To reflect in the prospectus any facts or events arising after the effective date of this
Registration Statement (or the most recent post-effective amendment thereof) which, individually or
in the aggregate, represent a fundamental change in the information set forth in this Registration
Statement. Notwithstanding the foregoing, any increase or decrease in volume of securities offered
(if the total dollar value of securities offered would not exceed that which was registered) and
any deviation from the low or high end of the estimated maximum offering range may be reflected in
the form of prospectus filed with the Commission pursuant to Rule 424(b) if, in the aggregate, the
changes in volume and price represent no more than 20&nbsp;percent change in the maximum aggregate
offering price set forth in the &#147;Calculation of Registration Fee&#148; table in this effective
Registration Statement;
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(iii)&nbsp;To include any material information with respect to the plan of distribution not
previously disclosed in this Registration Statement or any material change to such information in
this Registration Statement;
</DIV>
<DIV align="left" style="font-size: 10pt; margin-top: 6pt"><I>provided, however</I>, that paragraphs (a)(1)(i) and (a)(1)(ii) do not apply if this Registration
Statement is on Form S-3, Form S-8 or Form F-3, and the information required to be included in a
post-effective amendment by those paragraphs is contained in reports filed with or furnished to the
Commission by the registrant pursuant to Section&nbsp;13 or Section 15(d) of the Exchange Act that are
incorporated by reference in this Registration Statement;
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">(2)&nbsp;That, for the purpose of determining any liability under the Securities Act, each such
post-effective amendment shall be deemed to be a new registration statement relating to the
securities offered therein, and the offering of such securities at that time shall be deemed to be
the initial bona fide offering thereof.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">(3)&nbsp;To remove from registration by means of a post-effective amendment any of the securities being
registered which remain unsold at the termination of the offering.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">(b)&nbsp;The undersigned registrant hereby undertakes that, for purposes of determining any liability
under the Securities Act, each filing of the registrant&#146;s annual report pursuant to Section 13(a)
or Section 15(d) of the Exchange Act (and, where applicable, each filing of an employee benefit
plan&#146;s annual report pursuant to Section 15(d) of the Exchange Act) that is incorporated by
reference in this Registration Statement shall be deemed to be a new registration statement
relating to the securities offered therein, and the offering of such securities at that time shall
be deemed to be the initial bona fide offering thereof.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">(c)&nbsp;Insofar as indemnification for liabilities arising under the Securities Act may be permitted to
directors, officers and controlling persons of the Registrant pursuant to the indemnification
provisions summarized in Item&nbsp;6 or otherwise, the registrant has been advised that in the opinion
of the Commission such indemnification is against public policy as expressed in the Securities Act
and is,
</DIV>
<P align="center" style="font-size: 10pt">4
</DIV>

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<P><HR noshade><P>
<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif">


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">therefore, unenforceable. In the event that a claim for indemnification against such liabilities
(other than the payment by the registrant of expenses incurred or paid by the director, officer or
controlling person of the registrant in the successful defense of any action, suit or proceeding)
is asserted by such director, officer or controlling person in connection with the securities being
registered, the Registrant will, unless in the opinion of its counsel the matter has been settled
by controlling precedent, submit to a court of appropriate jurisdiction the question whether such
indemnification by it is against public policy as expressed in the Securities Act and will be
governed by the final adjudication of such issue.
</DIV>


<P align="center" style="font-size: 10pt">5
</DIV>

<!-- PAGEBREAK -->
<P><HR noshade><P>
<H5 align="left" style="page-break-before:always"><A HREF="#toc">Table of Contents</A></H5><P>

<DIV style="font-family: 'Times New Roman',Times,serif">
<!-- link1 "SIGNATURES" -->
<DIV align="left"><A NAME="009"></A></DIV>

<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>SIGNATURES</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Pursuant to the requirements of the Securities Act of 1933 (the &#147;Securities Act&#148;), the
Registrant certifies that it has reasonable grounds to believe that it meets all of the
requirements for filing on Form S-8 and has duly caused this Registration Statement to be signed
on its behalf by the undersigned, thereunto duly authorized, in the City of Farmington, State of
Connecticut on May&nbsp;23, 2006.
</DIV>
<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
    <TD width="48%">&nbsp;</TD>
    <TD width="2%">&nbsp;</TD>
    <TD width="2%">&nbsp;</TD>
    <TD width="2%">&nbsp;</TD>
    <TD width="36%">&nbsp;</TD>
    <TD width="2%">&nbsp;</TD>
    <TD width="10%">&nbsp;</TD>
</TR>
<!-- End Table Head -->
<!-- Begin Table Body -->
<TR valign="bottom">
    <TD valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD colspan="3" valign="top" align="left">DARWIN PROFESSIONAL UNDERWRITERS, INC.</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">By:
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">/s/ <FONT style="font-variant: SMALL-CAPS">Stephen J. Sills</FONT></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR style="font-size: 1px">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top" style="border-top: 1px solid #000000">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Stephen J. Sills<BR></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">President, Chief Executive Officer and Chairman of the Board of Directors</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<!-- End Table Body -->
</TABLE>
</DIV>


<DIV align="center" style="font-size: 10pt; margin-top: 18pt"><B>POWER OF ATTORNEY</B>
</DIV>


<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;KNOW ALL PERSONS BY THESE PRESENTS, that each of the persons whose names appear below
constitute and appoint Stephen J. Sills and John L. Sennott, Jr., and each of them, his true and
lawful attorney in fact and agent, with full power of substitution and resubstitution, for him
and in his name, place and stead, in any and all capacities, to execute any and all amendments
(including post-effective amendments) to this Registration Statement (or any other registration
statement for the same offering that is to be effective upon filing pursuant to Rule 462(b)
under the Securities Act of 1933), and to file the same, together with all exhibits thereto, and
other documents in connection therewith, with the Securities and Exchange Commission, and such
other agencies, offices and persons as may be required by applicable law, granting unto said
attorney in fact and agent, full power and authority to do and perform each and every act and
thing requisite or necessary to be done in and about the premises, as fully to all intents and
purposes as he might or could do in person, hereby ratifying and confirming all that each said
attorney-in-fact and agent may lawfully do or cause to be done by virtue hereof.
</DIV>

<DIV align="left" style="font-size: 10pt; margin-top: 6pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Pursuant to the requirements of the Securities Act of 1933, this Registration Statement has
been signed by the following persons in the capacities and on the dates indicated.
</DIV>

<DIV style="font-family: 'Times New Roman',Times,serif">
<DIV align="center">
<TABLE style="font-size: 10pt" cellspacing="0" border="0" cellpadding="0" width="100%">
<!-- Begin Table Head -->
<TR valign="bottom">
    <TD width="47%">&nbsp;</TD>
    <TD width="5%">&nbsp;</TD>
    <TD width="29%">&nbsp;</TD>
    <TD width="5%">&nbsp;</TD>
    <TD width="14%">&nbsp;</TD>
</TR>
<TR style="font-size: 8pt" valign="bottom">
    <TD nowrap align="center" style="border-bottom: 1px solid #000000">Signature</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="left" style="border-bottom: 1px solid #000000">&nbsp;&nbsp;&nbsp;Capacity</TD>
    <TD>&nbsp;</TD>
    <TD nowrap align="left" style="border-bottom: 1px solid #000000">Date</TD>
</TR>

<!-- End Table Head -->
<!-- Begin Table Body -->
<TR><TD>&nbsp;</TD></TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Stephen J. Sills</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Stephen J. Sills
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">President, Chief
Executive Officer
and Chairman of the
Board of Directors
(Principal
Executive Officer)
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May&nbsp;23, 2006</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">John L. Sennott, Jr.</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
John L. Sennott, Jr.
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Senior Vice
President, Chief
Financial Officer
and Director
(Principal
Financial and
Accounting Officer)
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May&nbsp;23, 2006</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Christopher K. Dalrymple</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Christopher K. Dalrymple
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Secretary, Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May&nbsp;23, 2006</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">R. Bruce Albro</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
R. Bruce Albro
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May&nbsp;23, 2006</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Robert V. Deutsch</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Robert V. Deutsch
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May&nbsp;23, 2006</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Phillip N. Ben-Zvi</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Phillip N. Ben-Zvi
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May&nbsp;23, 2006</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">Weston M. Hicks</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
Weston M. Hicks
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May&nbsp;23, 2006</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">&nbsp;</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/ <FONT style="font-variant: SMALL-CAPS">William C. Popik, M.D.</FONT>
<DIV style="font-size: 1pt; border-top: 1px solid #000000">&nbsp;</DIV>
William C. Popik, M.D.
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May&nbsp;23, 2006</TD>
</TR>


<TD valign="top"><DIV style="margin-left:0px; text-indent:-0px"></DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>


<TR valign="bottom"><!-- Blank Space -->

<TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/<FONT style="font-variant: SMALL-CAPS">
George M. Reider, Jr.</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>
<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px"><DIV style="border-bottom: 1px solid #000000; font-size: 1px">&nbsp;</DIV>
George M. Reider, Jr.
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May 23, 2006</TD>
</TR>
<TR valign="bottom"><!-- Blank Space -->

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<TD valign="top"><DIV style="margin-left:0px; text-indent:-0px"></DIV></TD>
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    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>

<TD valign="top"><DIV style="margin-left:0px; text-indent:-0px">/s/<FONT style="font-variant: SMALL-CAPS">
James P. Slattery</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">&nbsp;</TD>
</TR>

<TR valign="bottom">
    <TD valign="top"><DIV style="margin-left:0px; text-indent:-0px"><DIV style="border-bottom: 1px solid #000000; font-size: 1px">&nbsp;</DIV>
James P. Slattery
</DIV></TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">Director
</TD>
    <TD>&nbsp;</TD>
    <TD align="left" valign="top">May 23, 2006</TD>
</TR>
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{"company-data": {"conformed-name": "Darwin Professional Underwriters Inc", "cik": "0001355795", "assigned-sic": "6331", "irs-number": "030510450", "state-of-incorporation": "DE", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-134416", "film-number": "06862795"}, "business-address": {"street1": "9 FARM SPRINGS ROAD", "city": "FARMINGTON", "state": "CT", "zip": "06032", "phone": "860-284-1300"}, "mail-address": {"street1": "9 FARM SPRINGS ROAD", "city": "FARMINGTON", "state": "CT", "zip": "06032"}}
FORM S-8
Table of Contents
As filed with the Securities and Exchange Commission on May 23, 2006
Registration No. 333-
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
Form S-8
REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933
DARWIN PROFESSIONAL UNDERWRITERS, INC.
(Exact name of Registrant as specified in its charter)
Delaware
03-0510450
(State or other jurisdiction of
(I.R.S. Employer
incorporation or organization)
Identification Number)
9 Farm Springs Road
Farmington, Connecticut 06032
(860) 284-1300
(Address of Principal Executive Offices) (Zip Code)
Darwin
Professional Underwriters, Inc. 2006 Stock Incentive Plan
(Full title of the plan)
Stephen Sills
President and Chief Executive Officer
9 Farm Springs Road
Farmington, Connecticut 06032
(Name and address of agent for service)
Telephone number, including area code, of agent for service:
(860) 284-1300
CALCULATION OF REGISTRATION FEE
Proposed Maximum
Amount of
Title of Each Class of
Proposed Maximum Offering Price Per
Aggregate Offering
Registration
Securities to be Registered
Amount To Be Registered (1)
Share (2)
Price(2)
Fee
Common Stock, $0.01
par value per share
850,000
$18.55
$15,767,500.00
$1,687.12
(1)
Plus such additional shares as may be issued by reason of stock splits, stock dividends or
similar transactions.
(2)
Pursuant to Rules 457(h) and 457(c), these prices are estimated solely for the purpose of
calculating the registration fee and are based upon the average of the high and low sales
prices of the Registrant's common stock on the NYSE Arca Exchange on May 22, 2006.
TABLE OF CONTENTS
PART I
PART II
Item 3. Incorporation of Documents by Reference
Item 4. Description of Securities
Item 5. Interests of Named Experts and Counsel
Item 6. Indemnification of Directors and Officers
Item 7. Exemption from Registration Claimed
Item 8. Exhibits
Item 9. Undertakings
SIGNATURES
EX-5.1: OPINION OF DEWEY BALLANTINE LLP
EX-10.1: STOCK INCENTIVE PLAN
EX-23.2: CONSENT OF KPMG LLP
Table of Contents
PART I
INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS
The document(s) containing the information specified by Part I of this Form S-8 Registration
Statement (the "Registration Statement") will be sent or given to participants in the plan listed
on the cover of this Registration Statement (the "Plan") as specified by Rule 428(b)(1) promulgated
by the Securities and Exchange Commission (the "Commission") under the Securities Act of 1933, as
amended (the "Securities Act"). Such document(s) are not being filed with the Commission but
constitute (along with the documents incorporated by reference in this Registration Statement
pursuant to Item 3 of Part II hereof) a prospectus that meets the requirements of Section 10(a) of
the Securities Act.
PART II
Item 3. Incorporation of Documents by Reference.
The following documents filed with the Commission by the Registrant are incorporated herein by
reference and made a part hereof:
(a) The Registrant's Prospectus filed with the Commission on May 22, 2006 pursuant to rule
424(b) under the Securities Act;
(b) The Registrant's Current Report on Form 8-K filed with the Commission on May 23, 2006; and
(c) The description of the Registrant's Common Stock in the Registrant's Registration
Statement on Form 8-A, File No. 001-32883, filed with the Commission on May 16, 2006 pursuant to
Section 12 of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), including any
further amendments or reports filed for the purpose of updating such description.
All other documents subsequently filed by the Registrant pursuant to Sections 13(a), 13(c), 14
and 15(d) of the Exchange Act prior to the filing of a post-effective amendment which indicates
that all securities offered hereunder have been sold or which deregisters all such securities then
remaining unsold shall be deemed to be incorporated by reference in this Registration Statement and
be a part hereof from the date of filing of such documents.
Any statement contained herein or in a document incorporated or deemed to be incorporated by
reference herein shall be deemed to be modified or superseded for purposes of this Registration
Statement to the extent that a statement contained herein or in any other subsequently filed
document which also is or is deemed to be incorporated by reference herein modifies or supersedes
such earlier statement. Any statement so modified or superseded shall not be deemed, except as so
modified or superseded, to constitute a part of this Registration Statement.
Item 4. Description of Securities.
Not applicable.
Item 5. Interests of Named Experts and Counsel.
Not applicable.
Item 6. Indemnification of Directors and Officers.
Section 145(a) of the General Corporation Law of the State of Delaware (the "DGCL") provides
that a Delaware corporation may indemnify any person who was or is a party or is threatened to be
made a party to any threatened, pending or completed action, suit or proceeding, whether civil,
criminal, administrative or investigative (other than an action by or in the right of the
corporation) by reason of the fact that he is or was a director, officer, employee or agent of the
corporation or is or was serving at the request of the corporation as a director, officer, employee
or agent of another corporation or enterprise, against expenses, judgments, fines and amounts paid
in settlement actually and reasonably incurred by him in connection with such action, suit or
proceeding if he acted in good faith and in a manner he reasonably believed to be in or not opposed
to the best interests of the corporation, and, with respect to any criminal action or proceeding,
he had no cause to believe his conduct was unlawful.
2
Table of Contents
Section 145(b) of the DGCL provides that a Delaware corporation may indemnify any person who
was or is a party or is threatened to be made a party to any threatened, pending or completed
action or suit by or in the right of the corporation to procure a judgment in its favor by reason
of the fact that such person acted in any of the capacities set forth above, against expenses
actually and reasonably incurred by him in connection with the defense or settlement of such action
or suit if he acted under similar standards, except that no indemnification may be made in respect
of any claim, issue or matter as to which such person shall have been adjudged to be liable to the
corporation unless and only to the extent that the court in which such action or suit was brought
shall determine that despite the adjudication of liability, such person is fairly and reasonably
entitled to be indemnified for such expenses which the court shall deem proper.
Section 145 of the DGCL further provides that to the extent a director or officer of a
corporation has been successful in the defense of any action, suit or proceeding referred to in
subsections (a) and (b) or in the defense of any claim, issue, or matter therein, he shall be
indemnified against expenses (including attorneys' fees) actually and reasonably incurred by him in
connection therewith; that indemnification provided for by Section 145 shall not be deemed
exclusive of any other rights to which the indemnified party may be entitled; and that the
corporation may purchase and maintain insurance on behalf of a director or officer of the
corporation against any liability asserted against him or incurred by him in any such capacity or
arising out of his status as such whether or not the corporation would have the power to indemnify
him against such liabilities under such Section 145.
Section 102(b)(7) of the DGCL provides that a corporation in its original certificate of
incorporation or an amendment thereto validly approved by stockholders may eliminate or limit
personal liability of members of its board of directors or governing body for breach of a
director's fiduciary duty. However, no such provision may eliminate or limit the liability of a
director for breaching his duty of loyalty, failing to act in good faith, engaging in intentional
misconduct or knowingly violating a law, paying a dividend or approving a stock repurchase which
was illegal, or obtaining an improper personal benefit. A provision of this type has no effect on
the availability of equitable remedies, such as injunction or rescission, for breach of fiduciary
duty.
The Registrant's Certificate of Incorporation and By-Laws provide that the Registrant shall
indemnify officers, directors, employees and agents of the Registrant, to the full extent permitted
by and in the manner permissible under the laws of the State of Delaware. In addition, the
Certificate of Incorporation permits the board of directors to authorize the Registrant to purchase
and maintain insurance against any liability asserted against any director, officer, employee or
agent of the Registrant arising out of his capacity as such.
Alleghany Corporation maintains liability insurance for its directors and officers and for the
directors and officers of its majority-owned subsidiaries, including us. This insurance provides
for coverage, subject to certain exceptions, against loss from claims made against directors and
officers in their capacity as such, including claims under the federal securities laws.
Item 7. Exemption from Registration Claimed.
Not applicable.
Item 8. Exhibits.
Exhibit
Number
Description
3.1.1
Certificate of Incorporation of the Registrant. (Incorporated by reference to Exhibit 3.1.1 of the Registrant's
Registration Statement on Form S-1, as amended, File No. 333-132355).
3.1.2
Certificate of Amendment to Certificate of Incorporation of the Registrant dated November 30, 2005. (Incorporated
by reference to Exhibit 3.1.2 of the Registrant's Registration Statement on Form S-1, as amended, File No.
333-132355).
3.1.3
Certificate of Amendment to Certificate of Incorporation of the Registrant dated May 15, 2006. (Incorporated by
reference to Exhibit 3.1.3 of the Registrant's Registration Statement on Form S-1, as amended, File No.
333-132355).
3.1.4
Form of Amended and Restated Certificate of Incorporation (to be effective upon the completion of the
Registrant's initial public offering). (Incorporated by reference to Exhibit 3.1.4 of the Registrant's
Registration Statement on Form S-1, as amended, File No. 333-132355).
3.2
Amended and Restated By-laws. (Incorporated by reference to Exhibit 3.2 of the Registrant's Registration
Statement on Form S-1, as amended, File No. 333-1323556).
3
Table of Contents
Exhibit
Number
Description
4.1
Specimen Stock Certificate. (Incorporated by reference to Exhibit 4.1 of the Registrant's Registration Statement
on Form S-1, as amended, File No. 333-1323556).
4.2
Registration Rights Agreement by and between the Registrant and Alleghany Insurance Holdings LLC. (Incorporated
by reference to Exhibit 4.1 of the Registrant's current report on Form 8-K filed with the Commission on May 23,
2006).
4.3
Master Agreement by and between the Registrant and Alleghany Corporation. (Incorporated by reference to Exhibit
4.2 of the Registrant's current report on Form 8-K filed with the Commission on May 23, 2006).
5.1
Opinion of Dewey Ballantine LLP will respect to the legality of the securities being registered. (Filed herewith).
10.1
Darwin Professional Underwriters,
Inc. 2006 Stock Incentive Plan. (Filed herewith).
23.1
Consent of Dewey Ballantine LLP. (Included in Exhibit 5.1 hereto).
23.2
Consent of KPMG LLP. (Filed herewith).
24.1
Power of Attorney of directors and
certain officers of the Registrant. (Included on Signature Page).
Item 9. Undertakings.
(a) The undersigned Registrant hereby undertakes:
(1) To file, during any period in which offers or sales are being made, a post-effective amendment
to this Registration Statement:
(i) To include any prospectus required by Section 10(a)(3) of the Securities Act;
(ii) To reflect in the prospectus any facts or events arising after the effective date of this
Registration Statement (or the most recent post-effective amendment thereof) which, individually or
in the aggregate, represent a fundamental change in the information set forth in this Registration
Statement. Notwithstanding the foregoing, any increase or decrease in volume of securities offered
(if the total dollar value of securities offered would not exceed that which was registered) and
any deviation from the low or high end of the estimated maximum offering range may be reflected in
the form of prospectus filed with the Commission pursuant to Rule 424(b) if, in the aggregate, the
changes in volume and price represent no more than 20 percent change in the maximum aggregate
offering price set forth in the "Calculation of Registration Fee" table in this effective
Registration Statement;
(iii) To include any material information with respect to the plan of distribution not
previously disclosed in this Registration Statement or any material change to such information in
this Registration Statement;
provided, however
, that paragraphs (a)(1)(i) and (a)(1)(ii) do not apply if this Registration
Statement is on Form S-3, Form S-8 or Form F-3, and the information required to be included in a
post-effective amendment by those paragraphs is contained in reports filed with or furnished to the
Commission by the registrant pursuant to Section 13 or Section 15(d) of the Exchange Act that are
incorporated by reference in this Registration Statement;
(2) That, for the purpose of determining any liability under the Securities Act, each such
post-effective amendment shall be deemed to be a new registration statement relating to the
securities offered therein, and the offering of such securities at that time shall be deemed to be
the initial bona fide offering thereof.
(3) To remove from registration by means of a post-effective amendment any of the securities being
registered which remain unsold at the termination of the offering.
(b) The undersigned registrant hereby undertakes that, for purposes of determining any liability
under the Securities Act, each filing of the registrant's annual report pursuant to Section 13(a)
or Section 15(d) of the Exchange Act (and, where applicable, each filing of an employee benefit
plan's annual report pursuant to Section 15(d) of the Exchange Act) that is incorporated by
reference in this Registration Statement shall be deemed to be a new registration statement
relating to the securities offered therein, and the offering of such securities at that time shall
be deemed to be the initial bona fide offering thereof.
(c) Insofar as indemnification for liabilities arising under the Securities Act may be permitted to
directors, officers and controlling persons of the Registrant pursuant to the indemnification
provisions summarized in Item 6 or otherwise, the registrant has been advised that in the opinion
of the Commission such indemnification is against public policy as expressed in the Securities Act
and is,
4
Table of Contents
therefore, unenforceable. In the event that a claim for indemnification against such liabilities
(other than the payment by the registrant of expenses incurred or paid by the director, officer or
controlling person of the registrant in the successful defense of any action, suit or proceeding)
is asserted by such director, officer or controlling person in connection with the securities being
registered, the Registrant will, unless in the opinion of its counsel the matter has been settled
by controlling precedent, submit to a court of appropriate jurisdiction the question whether such
indemnification by it is against public policy as expressed in the Securities Act and will be
governed by the final adjudication of such issue.
5
Table of Contents
SIGNATURES
Pursuant to the requirements of the Securities Act of 1933 (the "Securities Act"), the
Registrant certifies that it has reasonable grounds to believe that it meets all of the
requirements for filing on Form S-8 and has duly caused this Registration Statement to be signed
on its behalf by the undersigned, thereunto duly authorized, in the City of Farmington, State of
Connecticut on May 23, 2006.
DARWIN PROFESSIONAL UNDERWRITERS, INC.
By:
/s/
Stephen J. Sills
Stephen J. Sills
President, Chief Executive Officer and Chairman of the Board of Directors
POWER OF ATTORNEY
KNOW ALL PERSONS BY THESE PRESENTS, that each of the persons whose names appear below
constitute and appoint Stephen J. Sills and John L. Sennott, Jr., and each of them, his true and
lawful attorney in fact and agent, with full power of substitution and resubstitution, for him
and in his name, place and stead, in any and all capacities, to execute any and all amendments
(including post-effective amendments) to this Registration Statement (or any other registration
statement for the same offering that is to be effective upon filing pursuant to Rule 462(b)
under the Securities Act of 1933), and to file the same, together with all exhibits thereto, and
other documents in connection therewith, with the Securities and Exchange Commission, and such
other agencies, offices and persons as may be required by applicable law, granting unto said
attorney in fact and agent, full power and authority to do and perform each and every act and
thing requisite or necessary to be done in and about the premises, as fully to all intents and
purposes as he might or could do in person, hereby ratifying and confirming all that each said
attorney-in-fact and agent may lawfully do or cause to be done by virtue hereof.
Pursuant to the requirements of the Securities Act of 1933, this Registration Statement has
been signed by the following persons in the capacities and on the dates indicated.
Signature
Capacity
Date
/s/
Stephen J. Sills
Stephen J. Sills
President, Chief
Executive Officer
and Chairman of the
Board of Directors
(Principal
Executive Officer)
May 23, 2006
/s/
John L. Sennott, Jr.
John L. Sennott, Jr.
Senior Vice
President, Chief
Financial Officer
and Director
(Principal
Financial and
Accounting Officer)
May 23, 2006
/s/
Christopher K. Dalrymple
Christopher K. Dalrymple
Secretary, Director
May 23, 2006
/s/
R. Bruce Albro
R. Bruce Albro
Director
May 23, 2006
/s/
Robert V. Deutsch
Robert V. Deutsch
Director
May 23, 2006
/s/
Phillip N. Ben-Zvi
Phillip N. Ben-Zvi
Director
May 23, 2006
/s/
Weston M. Hicks
Weston M. Hicks
Director
May 23, 2006
/s/
William C. Popik, M.D.
William C. Popik, M.D.
Director
May 23, 2006
/s/
George M. Reider, Jr.
George M. Reider, Jr.
Director
May 23, 2006
/s/
James P. Slattery
James P. Slattery
Director
May 23, 2006
6