X0202 4 2008-02-27 0 0001355795 Darwin Professional Underwriters Inc DR 0001362369 Sills Stephen Jay 9 FARM SPRINGS ROAD FARMINGTON CT 06032 1 1 0 0 President and CEO Common Stock 2008-02-27 4 A 0 7820 22.56 A 454018 D Common Stock 281205 I By Trusts Common Stock 1000 I By Child Common Stock 900 I By Child Common Stock 900 I By reporting person as UTMA custodian Common Stock 1050 I By child Employee Stock Option (right to buy) 22.56 2008-02-27 4 A 0 23335 A 2018-02-27 common stock 23335 23335 D Employee Stock Option (right to buy) 16.00 2016-05-19 common stock 57787 57787 D Employee Stock Option (right to buy) 25.30 2017-02-23 common stock 14365 14365 D Restricted stock award granted under Issuer's 2006 Stock Incentive Plan; price represents mean value of the high and low trades on the NYSE on February 27, 2008, the grant date, as per Plan spefication. Award vests and shares become unrestricted as follows: 50% of shares at February 27, 2011, and remainder at February 27, 2012. Held by grantor annuity trusts (GRATs), each of which the reporting person is sole trustee and beneficiary. Reporting person disclaims beneficial ownership of these shares. Employee stock option, granted 02/27/2008, under the Issuer's Stock Incentive Plan (the "Plan") at a fair market value determined in accordance with the Plan of $22.56 per share. Exercisable up to an aggregate of 25% on or after 02/27/ 2009, up to an aggregate of 50% on or after 02/27/2010, up to an aggregate of 75% on or after 02/23/2011 and in its entirety on or after 02/23/2012, subject to expiration or forfeiture in accordance with the Plan. The option vests in four equal installments. 25% vested on May 19, 2007, and the remaining 75% vests in equal installments on May 19, 2008, 2009 and 2010, subject to acceleration and/or forfeiture in accordance with the Stock Option Agreement. Employee stock option, granted 02/23/2007, under the issuer's 2006 Stock Incentive Plan (the "Plan") at a fair market value determined in accordance with the Plan of $25.30 per share. Exercisable up to an aggregate of 25% on or after 02/23/2008, up to an aggregate 50% on or after 02/23/2009, up to an aggregate 75% on or after 02/23/2010 and in its entirety on or after 02/23/2011, subject to expiration or forfeiture in accordance with the Plan. Stephen J. Sills, by Timothy J. Curry, attorney-in-fact 2008-02-29