X0306 4 2016-02-08 0 0001267395 ASPEN INSURANCE HOLDINGS LTD AHL 0001657825 Rheel Robert ASPEN INSURANCE HOLDINGS LTD 141 FRONT STREET HAMILTON D0 HM19 BERMUDA 0 1 0 0 President of U.S. Insurance Restricted Share Units (2016 Grant) 2016-02-08 4 A 0 3560 A Ordinary Shares 3560 3560 D Restricted Share Units (2015 Part Bonus) 2016-02-08 4 A 0 1745 A Ordinary Shares 1745 1745 D Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares. Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan. One-third of the 2016 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vest annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. /s/Silva Martinez as Attorney-in-fact for Robert Rheel 2016-02-10