X0306 4 2016-02-19 0 0001267395 ASPEN INSURANCE HOLDINGS LTD AHL 0001561304 Cain Michael ASPEN INSURANCE HOLDINGS LIMITED 141 FRONT STREET HAMILTON D0 HM19 BERMUDA 0 1 0 0 CEO, ABL & Group GC Ordinary Shares 2016-02-19 4 A 0 12565 A 39267 D Ordinary Shares 2016-02-22 4 F 0 3644 45.50 D 35623 D 2013 Performance Shares 2016-02-19 4 A 0 4624 A Ordinary Shares 4624 12565 D 2013 Performance Shares 2016-02-19 4 M 0 12565 D Ordinary Shares 12565 0 D 2014 Performance Shares 2016-02-19 4 A 0 4209 A Ordinary Shares 4209 10016 D 2015 Performance Shares 2016-02-19 4 A 0 3671 A Ordinary Shares 3671 3671 D Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met. Ordinary shares sold in order to satisfy tax liability upon vesting of previously granted Performance Shares. The price is the weighted average sale price of the aggregate number of shares that were sold by the reporting person. These shares were sold in multiple transactions at prices ranging from $45.3500 to $45.5800. The reporting person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price. Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. Represents 2013 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2013 Performance Share award is tested annually over a three-year period. All vested 2013 Performance Shares are issued following the filing of the annual report on Form 10-K for the year ended December 31, 2015. Represents mandatory conversion of all 2013 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer and filing of the annual report on Form 10-K for the year ended December 31, 2015. Represents 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2014 Performance Share award is tested annually over a three-year period. All vested 2014 Performance Shares are issued following the filing of the annual report on Form 10-K for the year ended December 31, 2016. Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period. All vested 2015 Performance Shares will be issued following the filing of the annual report on Form 10-K for the year ended December 31, 2017. /s/Silvia Martinez as Attorney-in-fact for Michael Cain 2016-02-23