AHL-PD

SEC source: 0001726121-19-000006 · wf-form4_155068657025776.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 · 9,030 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 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.

F2 · 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.

F2 · 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: 0001726121-19-000006 · wf-form4_155068657025776.xml · derivative · entry 1

Schick David Gerard · CIK 0001726121 · Group Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 9,030

Underlying: Ordinary Shares · 9,030 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 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.

F2 · 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.

F2 · 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: 0001562198-19-000006 · wf-form4_155068641913672.xml · derivative · entry 4

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 16,000 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: 0001562198-19-000006 · wf-form4_155068641913672.xml · derivative · entry 3

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 16,000

Underlying: Ordinary Shares · 16,000 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: 0001562198-19-000006 · wf-form4_155068641913672.xml · derivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 6,669 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: 0001562198-19-000006 · wf-form4_155068641913672.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 6,669

Underlying: Ordinary Shares · 6,669 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: 0001705105-19-000006 · wf-form4_155068623487041.xml · derivative · entry 2

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

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

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

F6 · price: At the effective time of the Merger, each 2018 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 2018 Phantom Share.

F5 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Phantom Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Phantom Share award was tested annually over a three-year period. All vested 2018 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, 2020. One third of the 2018 Phantom 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 Phantom 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 Phantom Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Phantom Share award was tested annually over a three-year period. All vested 2018 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, 2020. One third of the 2018 Phantom 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 Phantom Shares vested at target payout levels in connection with the Merger.

SEC source: 0001705105-19-000006 · wf-form4_155068623487041.xml · derivative · entry 1

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

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: 0001561518-19-000006 · wf-form4_155068603381081.xml · derivative · entry 4

Vacher Kate · CIK 0001561518 · CEO, ABL

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: 0001561518-19-000006 · wf-form4_155068603381081.xml · derivative · entry 3

Vacher Kate · CIK 0001561518 · CEO, ABL

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: 0001561518-19-000006 · wf-form4_155068603381081.xml · derivative · entry 2

Vacher Kate · CIK 0001561518 · CEO, ABL

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: 0001561518-19-000006 · wf-form4_155068603381081.xml · derivative · entry 1

Vacher Kate · CIK 0001561518 · CEO, ABL

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: 0001657961-19-000006 · wf-form4_155068575638580.xml · derivative · entry 4

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 12,500 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: 0001657961-19-000006 · wf-form4_155068575638580.xml · derivative · entry 3

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,500

Underlying: Ordinary Shares · 12,500 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: 0001657961-19-000006 · wf-form4_155068575638580.xml · derivative · entry 2

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 5,335 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: 0001657961-19-000006 · wf-form4_155068575638580.xml · derivative · entry 1

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,335

Underlying: Ordinary Shares · 5,335 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: 0001603733-19-000006 · wf-form4_155068556786483.xml · derivative · entry 4

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 20,000 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: 0001603733-19-000006 · wf-form4_155068556786483.xml · derivative · entry 3

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 20,000

Underlying: Ordinary Shares · 20,000 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: 0001603733-19-000006 · wf-form4_155068556786483.xml · derivative · entry 2

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 5,558 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: 0001603733-19-000006 · wf-form4_155068556786483.xml · derivative · entry 1

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,558

Underlying: Ordinary Shares · 5,558 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: 0001561313-19-000006 · wf-form4_155068530580321.xml · derivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 41,484 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: 0001561313-19-000006 · wf-form4_155068530580321.xml · derivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 41,484

Underlying: Ordinary Shares · 41,484 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: 0001561313-19-000006 · wf-form4_155068530580321.xml · derivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 17,784 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: 0001561313-19-000006 · wf-form4_155068530580321.xml · derivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,784

Underlying: Ordinary Shares · 17,784 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: 0001603733-19-000004 · wf-form4_155027058644812.xml · derivative · entry 4

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 2,373 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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.

F6 · derivative.exercise_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F6 · derivative.expiration_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

SEC source: 0001603733-19-000004 · wf-form4_155027058644812.xml · nonDerivative · entry 2

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 26,025

F2 · kind: Ordinary shares sold in order to satisfy tax liability upon vesting of previously granted Performance Shares.

SEC source: 0001603733-19-000004 · wf-form4_155027058644812.xml · nonDerivative · entry 1

Kirk Scott · CIK 0001603733 · Group CFO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 27,141

F1 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met.

SEC source: 0001718360-19-000004 · wf-form4_155027038880116.xml · derivative · entry 2

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 86 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Phantom Share represents the right to receive the economic equivalent of one of the Issuer's Ordinary Shares.

F3 · price: Each Phantom Share represents the right to receive the economic equivalent of one of the Issuer's Ordinary Shares.

F4 · derivative.exercise_date: Represents 2016 Phantom Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One-third of the 2016 Phantom Share award was tested annually over a three-year period. Subject to continued employment, all vested 2016 Phantom Shares were settled in cash upon the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F4 · derivative.expiration_date: Represents 2016 Phantom Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One-third of the 2016 Phantom Share award was tested annually over a three-year period. Subject to continued employment, all vested 2016 Phantom Shares were settled in cash upon the filing of the annual report on Form 10-K for the year ended December 31, 2018.

SEC source: 0001657961-19-000004 · wf-form4_155027048461500.xml · derivative · entry 4

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,780 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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.

F6 · derivative.exercise_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F6 · derivative.expiration_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

SEC source: 0001657961-19-000004 · wf-form4_155027048461500.xml · nonDerivative · entry 2

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,694

F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Performance Shares.

SEC source: 0001657961-19-000004 · wf-form4_155027048461500.xml · nonDerivative · entry 1

Cohen David Alan · CIK 0001657961 · President and CUO Insurance

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,299

F1 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met.

SEC source: 0001562198-19-000004 · wf-form4_155027021367945.xml · derivative · entry 4

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 2,966 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · derivative.exercise_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F7 · derivative.expiration_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

SEC source: 0001562198-19-000004 · wf-form4_155027021367945.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 14,537

F3 · kind: Ordinary shares sold in order to satisfy tax liability upon vesting of previously granted Performance Shares.

SEC source: 0001562198-19-000004 · wf-form4_155027021367945.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 15,332

F1 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met.

F2 · balance_after: The number of ordinary shares outstanding differs from the Reporting Person's previously filed Form 4 due to a transaction that was exempt from reporting on Form 4.

SEC source: 0001561518-19-000004 · wf-form4_155027009029907.xml · derivative · entry 4

Vacher Kate · CIK 0001561518 · CEO, ABL

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 1,187 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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.

F6 · derivative.exercise_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F6 · derivative.expiration_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

SEC source: 0001561518-19-000004 · wf-form4_155027009029907.xml · nonDerivative · entry 2

Vacher Kate · CIK 0001561518 · CEO, ABL

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 43,856

F2 · kind: Ordinary shares sold in order to satisfy tax liability upon vesting of previously granted Performance Shares.

SEC source: 0001561518-19-000004 · wf-form4_155027009029907.xml · nonDerivative · entry 1

Vacher Kate · CIK 0001561518 · CEO, ABL

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 44,130

F1 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met.

SEC source: 0001561304-19-000004 · wf-form4_155026997077642.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 · 1,385 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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.

F6 · derivative.exercise_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F6 · derivative.expiration_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

SEC source: 0001561304-19-000004 · wf-form4_155026997077642.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 65,534

F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Performance Shares.

SEC source: 0001561304-19-000004 · wf-form4_155026997077642.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 65,866

F1 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met.

SEC source: 0001705105-19-000004 · wf-form4_155026986376639.xml · derivative · entry 2

Dawe Grahame · CIK 0001705105 · Chief Accounting Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 178 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Phantom Share represents the right to receive the economic equivalent of one of the Issuer's Ordinary Shares.

F3 · price: Each Phantom Share represents the right to receive the economic equivalent of one of the Issuer's Ordinary Shares.

F4 · derivative.exercise_date: Represents 2016 Phantom Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Phantom Share award was tested annually over a three-year period. Subject to continued employment, all vested 2016 Phantom Shares were settled in cash upon the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F4 · derivative.expiration_date: Represents 2016 Phantom Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Phantom Share award was tested annually over a three-year period. Subject to continued employment, all vested 2016 Phantom Shares were settled in cash upon the filing of the annual report on Form 10-K for the year ended December 31, 2018.

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · derivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 7,909 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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.

F6 · derivative.exercise_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F6 · derivative.expiration_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · nonDerivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 238,494

F2 · kind: Ordinary shares sold in order to satisfy tax liability upon vesting of previously granted Performance Shares.

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 241,156

F1 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met.

SEC source: 0001718360-19-000002 · wf-form4_155000615015947.xml · derivative · entry 9

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 385

Underlying: Ordinary Shares · 385 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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.

F8 · derivative.exercise_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan, as amended. One-third of the 2017 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 2017 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.

F8 · derivative.expiration_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan, as amended. One-third of the 2017 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 2017 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.

SEC source: 0001718360-19-000002 · wf-form4_155000615015947.xml · nonDerivative · entry 6

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,402

F4 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2017 Restricted Share Units.

SEC source: 0001718360-19-000002 · wf-form4_155000615015947.xml · nonDerivative · entry 5

Brown Heather · CIK 0001718360 · Group HR Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,583

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

SEC source: 0001562198-19-000002 · wf-form4_155000476855974.xml · derivative · entry 9

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,556

Underlying: Ordinary Shares · 2,556 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F9 · derivative.exercise_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan, as amended. One-third of the 2017 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 2017 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.

F9 · derivative.expiration_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan, as amended. One-third of the 2017 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 2017 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.

SEC source: 0001562198-19-000002 · wf-form4_155000476855974.xml · nonDerivative · entry 6

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 15,848

F5 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2017 Restricted Share Units.

SEC source: 0001562198-19-000002 · wf-form4_155000476855974.xml · nonDerivative · entry 5

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 16,897

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.