AHL-PD

SEC source: 0001077710-19-000002 · wf-form4_155025682844796.xml · nonDerivative · entry 1

PEARLMAN BRET D · CIK 0001077710 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001164665-19-000003 · wf-form4_155025850089399.xml · nonDerivative · entry 1

HUTTER HEIDI · CIK 0001164665 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001181384-19-000002 · wf-form4_155025783136734.xml · nonDerivative · entry 1

CAVOORES JOHN PAUL · CIK 0001181384 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001469142-19-000002 · wf-form4_155025632113901.xml · nonDerivative · entry 1

Botein Matthew · CIK 0001469142 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001561308-19-000002 · wf-form4_155025819739100.xml · nonDerivative · entry 1

Beer Albert · CIK 0001561308 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001282620-19-000002 · wf-form4_155025607668751.xml · nonDerivative · entry 1

MAYR KARL · CIK 0001282620 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed in connection with the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001603733-19-000004 · wf-form4_155027058644812.xml · derivative · entry 6

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 6,666 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F11 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F10 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F10 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001603733-19-000004 · wf-form4_155027058644812.xml · derivative · entry 5

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,853 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F9 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F8 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F8 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001603733-19-000004 · wf-form4_155027058644812.xml · nonDerivative · entry 3

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F3 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F4 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001718360-19-000004 · wf-form4_155027038880116.xml · derivative · entry 4

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 2,333 shares

Expires not disclosed

F5 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F9 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F8 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F8 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001718360-19-000004 · wf-form4_155027038880116.xml · derivative · entry 3

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 385 shares

Expires not disclosed

F5 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F6 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F6 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001718360-19-000004 · wf-form4_155027038880116.xml · nonDerivative · entry 1

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001657961-19-000004 · wf-form4_155027048461500.xml · derivative · entry 6

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 4,166 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F11 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F10 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F10 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001657961-19-000004 · wf-form4_155027048461500.xml · derivative · entry 5

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,778 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F9 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F8 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F8 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001657961-19-000004 · wf-form4_155027048461500.xml · nonDerivative · entry 3

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F3 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F4 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001562198-19-000004 · wf-form4_155027021367945.xml · derivative · entry 6

Issavi Emil · CIK 0001562198 · President and CUO, Aspen Re

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 5,333 shares

Expires not disclosed

F8 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F8 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F12 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F11 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F11 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001562198-19-000004 · wf-form4_155027021367945.xml · derivative · entry 5

Issavi Emil · CIK 0001562198 · President and CUO, Aspen Re

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,556 shares

Expires not disclosed

F8 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F8 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F10 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F9 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F9 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001562198-19-000004 · wf-form4_155027021367945.xml · nonDerivative · entry 3

Issavi Emil · CIK 0001562198 · President and CUO, Aspen Re

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F4 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F5 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001561518-19-000004 · wf-form4_155027009029907.xml · derivative · entry 6

Vacher Kate · CIK 0001561518 · CEO, ABL

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 2,416 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F11 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F10 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F10 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001561518-19-000004 · wf-form4_155027009029907.xml · derivative · entry 5

Vacher Kate · CIK 0001561518 · CEO, ABL

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,112 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares.

F9 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F8 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F8 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001561518-19-000004 · wf-form4_155027009029907.xml · nonDerivative · entry 3

Vacher Kate · CIK 0001561518 · CEO, ABL

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F3 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F4 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001561304-19-000004 · wf-form4_155026997077642.xml · derivative · entry 6

Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 2,416 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F11 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F10 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F10 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001561304-19-000004 · wf-form4_155026997077642.xml · derivative · entry 5

Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,112 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F9 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F8 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F8 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001561304-19-000004 · wf-form4_155026997077642.xml · nonDerivative · entry 3

Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F3 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F4 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001705105-19-000004 · wf-form4_155026986376639.xml · derivative · entry 4

Dawe Grahame · CIK 0001705105 · Chief Accounting Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,234 shares

Expires not disclosed

F5 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F9 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F8 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F8 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001705105-19-000004 · wf-form4_155026986376639.xml · derivative · entry 3

Dawe Grahame · CIK 0001705105 · Chief Accounting Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 519 shares

Expires not disclosed

F5 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F6 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F6 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001705105-19-000004 · wf-form4_155026986376639.xml · nonDerivative · entry 1

Dawe Grahame · CIK 0001705105 · Chief Accounting Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001726121-19-000004 · wf-form4_155026974865749.xml · derivative · entry 2

Schick David Gerard · CIK 0001726121 · Group Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 3,010 shares

Expires not disclosed

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F4 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F4 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001726121-19-000004 · wf-form4_155026974865749.xml · nonDerivative · entry 1

Schick David Gerard · CIK 0001726121 · Group Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · derivative · entry 6

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 13,828 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F11 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F10 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F10 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · derivative · entry 5

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 5,928 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F9 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F8 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F8 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · nonDerivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F3 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F4 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001520674-19-000004 · wf-form4_155026949580329.xml · derivative · entry 3

Aman Timothy Paul · CIK 0001520674 · Group Chief Risk Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 2,333 shares

Expires not disclosed

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F6 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F6 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001520674-19-000004 · wf-form4_155026949580329.xml · derivative · entry 2

Aman Timothy Paul · CIK 0001520674 · Group Chief Risk Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,200 shares

Expires not disclosed

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F4 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

F4 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third 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.

SEC source: 0001520674-19-000004 · wf-form4_155026949580329.xml · nonDerivative · entry 1

Aman Timothy Paul · CIK 0001520674 · Group Chief Risk Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001561430-19-000002 · wf-form4_155025896284502.xml · nonDerivative · entry 1

Jones Glyn · CIK 0001561430 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001569317-19-000002 · wf-form4_155025871955556.xml · nonDerivative · entry 1

Ireland Gordon · CIK 0001569317 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001233170-19-000002 · wf-form4_155025808256521.xml · nonDerivative · entry 1

PRESSMAN RONALD R · CIK 0001233170 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001501790-19-000002 · wf-form4_155025669791207.xml · nonDerivative · entry 1

Gregg Gary R. · CIK 0001501790 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F1 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F2 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

SEC source: 0001561304-19-000006 · wf-form4_155068716642209.xml · derivative · entry 4

Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 7,250 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F5 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F5 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001561304-19-000006 · wf-form4_155068716642209.xml · derivative · entry 3

Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 7,250

Underlying: Ordinary Shares · 7,250 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F5 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F5 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001561304-19-000006 · wf-form4_155068716642209.xml · derivative · entry 2

Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 3,335 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F4 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F2 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

F2 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001561304-19-000006 · wf-form4_155068716642209.xml · derivative · entry 1

Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,335

Underlying: Ordinary Shares · 3,335 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F2 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

F2 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001718360-19-000006 · wf-form4_155068697261281.xml · derivative · entry 3

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 7,000 shares

Expires not disclosed

F5 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F6 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F6 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001718360-19-000006 · wf-form4_155068697261281.xml · derivative · entry 2

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 7,000

Underlying: Ordinary Shares · 7,000 shares

Expires not disclosed

F5 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F6 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F6 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001718360-19-000006 · wf-form4_155068697261281.xml · derivative · entry 1

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 385 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Phantom Share represents the right to receive the economic equivalent of one of the Issuer's Ordinary Shares.

F2 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F1 · price: Each Phantom Share represents the right to receive the economic equivalent of one of the Issuer's Ordinary Shares.

F4 · price: At the effective time of the Merger, each 2017 Phantom Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Phantom Share.

F3 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Phantom Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Phantom Share award was tested annually over a three-year period. All vested 2017 Phantom Shares would have been settled in cash upon the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Phantom Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Phantom Shares vested at target payout levels in connection with the Merger.

F3 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Phantom Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Phantom Share award was tested annually over a three-year period. All vested 2017 Phantom Shares would have been settled in cash upon the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Phantom Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Phantom Shares vested at target payout levels in connection with the Merger.

SEC source: 0001520674-19-000006 · wf-form4_155068675245412.xml · derivative · entry 4

Aman Timothy Paul · CIK 0001520674 · Group Chief Risk Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 7,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F5 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F5 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001520674-19-000006 · wf-form4_155068675245412.xml · derivative · entry 3

Aman Timothy Paul · CIK 0001520674 · Group Chief Risk Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 7,000

Underlying: Ordinary Shares · 7,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F5 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F5 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001520674-19-000006 · wf-form4_155068675245412.xml · derivative · entry 2

Aman Timothy Paul · CIK 0001520674 · Group Chief Risk Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 3,601 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F4 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F2 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

F2 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

SEC source: 0001520674-19-000006 · wf-form4_155068675245412.xml · derivative · entry 1

Aman Timothy Paul · CIK 0001520674 · Group Chief Risk Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,601

Underlying: Ordinary Shares · 3,601 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F2 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

F2 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.