person · Reporting owner

Cain Michael

Disclosed activity across 1 company

Tapewire entity: 160058
SEC CIK: 0001561304

Reported relationships

Latest disclosed role at each company.

Company	Last reported as	Report date	Published
ASPEN INSURANCE HOLDINGS LTDAHL · Entity 9774	CEO, AIUK, AMAL & Group GC	February 15, 2019	February 20, 2019

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

ASPEN INSURANCE HOLDINGS LTD

Report date February 15, 2019 · Filed February 20, 2019

Security / award	Ownership account	Disclosed shares / units	Disclosure context
2017 Performance SharesSEC Table II · derivative / convertible security	Direct	3,335	Reported balance After 2019-02-15 transaction · row 1 Instrument identity requires review; Table II rows are not merged. 1 source row Row 1 · 2019-02-15 · Grant · Acquired 3,335 · Balance 3,335 F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F3: 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: 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.
2017 Performance SharesSEC Table II · derivative / convertible security	Direct	0	Reported balance After 2019-02-15 transaction · row 2 Instrument identity requires review; Table II rows are not merged. 1 source row Row 2 · 2019-02-15 · Disposition to issuer · Disposed 3,335 · Balance 0 F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F4: 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. F3: 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: 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.
Performance Shares (2018 Grant)SEC Table II · derivative / convertible security	Direct	7,250	Reported balance After 2019-02-15 transaction · row 3 Instrument identity requires review; Table II rows are not merged. 1 source row Row 3 · 2019-02-15 · Grant · Acquired 7,250 · Balance 7,250 F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F6: 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: 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.
Performance Shares (2018 Grant)SEC Table II · derivative / convertible security	Direct	0	Reported balance After 2019-02-15 transaction · row 4 Instrument identity requires review; Table II rows are not merged. 1 source row Row 4 · 2019-02-15 · Disposition to issuer · Disposed 7,250 · Balance 0 F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F6: 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: 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.

Filing footnotes · ownership attribution and instrument terms

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

F2: 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.

F3: 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.

F4: 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.

F5: 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: 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.

Transaction history

JSON API

Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction date	Company	Activity / security	Shares / units	Reported price	Reported value	Details
February 15, 2019 Filed Feb 15, 2019 22:33 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Disposition to issuerRestricted Share Units (2018 Grant) · Derivative	2,416	Not disclosed	Not disclosed	Disclosure 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. Read SEC document
February 15, 2019 Filed Feb 15, 2019 22:33 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Disposition to issuerRestricted Share Units (2017 Grant) · Derivative	1,112	Not disclosed	Not disclosed	Disclosure 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. Read SEC document
February 15, 2019 Filed Feb 15, 2019 22:33 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Disposition to issuerOrdinary Shares	65,534	$42.75	$2,801,578.50	Disclosure 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. Read SEC document
February 15, 2019 Filed Feb 20, 2019 18:26 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Disposition to issuerPerformance Shares (2018 Grant) · Derivative	7,250	Not disclosed	Not disclosed	Disclosure 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. Read SEC document
February 15, 2019 Filed Feb 20, 2019 18:26 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantPerformance Shares (2018 Grant) · Derivative	7,250	Not disclosed	Not disclosed	Disclosure 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. Read SEC document
February 15, 2019 Filed Feb 20, 2019 18:26 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Disposition to issuer2017 Performance Shares · Derivative	3,335	Not disclosed	Not disclosed	Disclosure 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. Read SEC document
February 15, 2019 Filed Feb 20, 2019 18:26 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Grant2017 Performance Shares · Derivative	3,335	Not disclosed	Not disclosed	Disclosure 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. Read SEC document
February 13, 2019 Filed Feb 15, 2019 22:33 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversion2016 Performance Shares · Derivative	1,385	Not disclosed	Not disclosed	Disclosure 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. Read SEC document
February 13, 2019 Filed Feb 15, 2019 22:33 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	332	$42.51	$14,113.32	Disclosure 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. Read SEC document
February 13, 2019 Filed Feb 15, 2019 22:33 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,385	Not disclosed	Not disclosed	Disclosure 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. Read SEC document
February 10, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2017 Grant) · Derivative	1,111	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · derivative · entry 12 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 1,112 Underlying: Ordinary Shares · 1,111 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. F10 · 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. F10 · 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. Read SEC document
February 10, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	372	$42.56	$15,832.32	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · nonDerivative · entry 8 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 64,481 F5 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2017 Restricted Share Units. Read SEC document
February 10, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,111	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · nonDerivative · entry 7 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 64,853 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
February 09, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2018 Grant) · Derivative	1,209	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · derivative · entry 11 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 2,416 Underlying: Ordinary Shares · 1,209 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 2018 Restricted Share Units granted on February 9, 2018 under our 2013 Share Incentive Plan, as amended. One-third of the 2018 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 2018 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 2018 Restricted Share Units granted on February 9, 2018 under our 2013 Share Incentive Plan, as amended. One-third of the 2018 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 2018 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. Read SEC document
February 09, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	405	$42.56	$17,236.80	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · nonDerivative · entry 6 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 63,742 F4 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2018 Restricted Share Units. Read SEC document
February 09, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,209	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · nonDerivative · entry 5 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 64,147 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2016 Grant) · Derivative	1,278	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · derivative · entry 10 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 0 Underlying: Ordinary Shares · 1,278 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. F8 · derivative.exercise_date: Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan, as amended. One-third of the 2016 Restricted Share Units vested annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. F8 · derivative.expiration_date: Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan, as amended. One-third of the 2016 Restricted Share Units vested annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2015 Part Bonus) · Derivative	720	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · derivative · entry 9 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 0 Underlying: Ordinary Shares · 720 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. F7 · derivative.exercise_date: Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vested annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. F7 · derivative.expiration_date: Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vested annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	428	$42.56	$18,215.68	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · nonDerivative · entry 4 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 62,938 F3 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2016 Restricted Share Units. Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,278	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · nonDerivative · entry 3 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 63,366 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	241	$42.56	$10,256.96	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · nonDerivative · entry 2 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 62,088 F2 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2015 Part Bonus Restricted Share Units. Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:39 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	720	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-19-000002 · wf-form4_155000397244078.xml · nonDerivative · entry 1 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 62,329 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
March 05, 2018 Filed Mar 7, 2018 21:07 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversion2015 Performance Shares · Derivative	5,088	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000006 · wf-form4_152045683563546.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 · 5,088 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. F7 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F7 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F8 · derivative.exercise_date: Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period. F8 · derivative.expiration_date: Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period. Read SEC document
March 05, 2018 Filed Mar 7, 2018 21:07 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2015 Grant) · Derivative	1,308	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000006 · wf-form4_152045683563546.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 · 1,308 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. F6 · derivative.exercise_date: Represents 2015 Restricted Share Units granted on March 5, 2015 under our 2013 Share Incentive Plan, as amended. One-third of the 2015 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 2015 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. F6 · derivative.expiration_date: Represents 2015 Restricted Share Units granted on March 5, 2015 under our 2013 Share Incentive Plan, as amended. One-third of the 2015 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 2015 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. Read SEC document
March 05, 2018 Filed Mar 7, 2018 21:07 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	472	$37.95	$17,912.40	Disclosure SEC source: 0001561304-18-000006 · wf-form4_152045683563546.xml · nonDerivative · entry 4 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 61,609 F4 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Performance Shares. Read SEC document
March 05, 2018 Filed Mar 7, 2018 21:07 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	5,088	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000006 · wf-form4_152045683563546.xml · nonDerivative · entry 3 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 62,081 F3 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met. Read SEC document
March 05, 2018 Filed Mar 7, 2018 21:07 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	122	$37.95	$4,629.90	Disclosure SEC source: 0001561304-18-000006 · wf-form4_152045683563546.xml · nonDerivative · entry 2 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 56,993 F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units. Read SEC document
March 05, 2018 Filed Mar 7, 2018 21:07 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,308	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000006 · wf-form4_152045683563546.xml · nonDerivative · entry 1 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 57,115 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
February 10, 2018 Filed Feb 14, 2018 00:04 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2017 Grant) · Derivative	1,112	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000004 · wf-form4_151856667810309.xml · derivative · entry 3 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 2,223 Underlying: Ordinary Shares · 1,112 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 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. F4 · 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. F4 · 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. Read SEC document
February 10, 2018 Filed Feb 14, 2018 00:04 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	278	$36.75	$10,216.50	Disclosure SEC source: 0001561304-18-000004 · wf-form4_151856667810309.xml · nonDerivative · entry 2 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 55,807 F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units. Read SEC document
February 10, 2018 Filed Feb 14, 2018 00:04 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,112	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000004 · wf-form4_151856667810309.xml · nonDerivative · entry 1 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 56,085 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
February 09, 2018 Filed Feb 14, 2018 00:04 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantRestricted Share Units (2018 Grant) · Derivative	3,625	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000004 · wf-form4_151856667810309.xml · derivative · entry 4 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 3,625 Underlying: Ordinary Shares · 3,625 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 · derivative.exercise_date: Represents 2018 Restricted Share Units granted on February 9, 2018 under our 2013 Share Incentive Plan, as amended. One-third of the 2018 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 2018 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. F5 · derivative.expiration_date: Represents 2018 Restricted Share Units granted on February 9, 2018 under our 2013 Share Incentive Plan, as amended. One-third of the 2018 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 2018 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. Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:09 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2015 Part Bonus) · Derivative	719	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000002 · wf-form4_151845173644889.xml · derivative · entry 6 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 720 Underlying: Ordinary Shares · 719 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 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 · derivative.exercise_date: Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vest annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. F5 · derivative.expiration_date: Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vest annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:09 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2016 Grant) · Derivative	1,278	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000002 · wf-form4_151845173644889.xml · derivative · entry 5 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 1,278 Underlying: Ordinary Shares · 1,278 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 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. F4 · derivative.exercise_date: Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan, as amended. One-third of the 2016 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. F4 · derivative.expiration_date: Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan, as amended. One-third of the 2016 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:09 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	89	$37.00	$3,293.00	Disclosure SEC source: 0001561304-18-000002 · wf-form4_151845173644889.xml · nonDerivative · entry 4 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 54,973 F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units. Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:09 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	719	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000002 · wf-form4_151845173644889.xml · nonDerivative · entry 3 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 55,062 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:09 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	158	$37.00	$5,846.00	Disclosure SEC source: 0001561304-18-000002 · wf-form4_151845173644889.xml · nonDerivative · entry 2 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 54,343 F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units. Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:09 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,278	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-18-000002 · wf-form4_151845173644889.xml · nonDerivative · entry 1 Cain Michael · CIK 0001561304 · CEO, AIUK, AMAL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 54,501 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
April 25, 2017 Filed Apr 27, 2017 17:52 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2014 Grant) · Derivative	1,500	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000010 · wf-form4_149331555495975.xml · derivative · entry 3 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 0 Underlying: Ordinary Shares · 1,500 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 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. F4 · derivative.exercise_date: Represents 2014 Restricted Share Units granted on April 25, 2014 under our 2013 Share Incentive Plan as amended. One-third of the 2014 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 2014 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. F4 · derivative.expiration_date: Represents 2014 Restricted Share Units granted on April 25, 2014 under our 2013 Share Incentive Plan as amended. One-third of the 2014 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 2014 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. Read SEC document
April 25, 2017 Filed Apr 27, 2017 17:52 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	155	$51.50	$7,982.50	Disclosure SEC source: 0001561304-17-000010 · wf-form4_149331555495975.xml · nonDerivative · entry 2 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 52,882 F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units. Read SEC document
April 25, 2017 Filed Apr 27, 2017 17:52 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,500	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000010 · wf-form4_149331555495975.xml · nonDerivative · entry 1 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 53,037 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
March 05, 2017 Filed Mar 7, 2017 15:31 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversionRestricted Share Units (2015 Grant) · Derivative	1,308	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000008 · wf-form4_148890066427245.xml · derivative · entry 2 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 1,308 Underlying: Ordinary Shares · 1,308 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. F2 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares. F2 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares. F3 · derivative.exercise_date: Represents 2015 Restricted Share Units granted on March 5, 2015 under our 2013 Share Incentive Plan. One-third of the 2015 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 2015 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. F3 · derivative.expiration_date: Represents 2015 Restricted Share Units granted on March 5, 2015 under our 2013 Share Incentive Plan. One-third of the 2015 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 2015 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting. Read SEC document
March 05, 2017 Filed Mar 7, 2017 15:31 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	1,308	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000008 · wf-form4_148890066427245.xml · nonDerivative · entry 1 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 51,537 F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units. Read SEC document
February 22, 2017 Filed Feb 24, 2017 22:58 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Grant2016 Performance Shares · Derivative	1,384	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000006 · wf-form4_148797708545117.xml · derivative · entry 6 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 1,384 Underlying: Ordinary Shares · 1,384 shares Expires not disclosed F3 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F3 · 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 is tested annually over a three-year period. All vested 2016 Performance Shares will be 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 is tested annually over a three-year period. All vested 2016 Performance Shares will be issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018. Read SEC document
February 22, 2017 Filed Feb 24, 2017 22:58 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Grant2015 Performance Shares · Derivative	1,417	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000006 · wf-form4_148797708545117.xml · derivative · entry 5 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 5,088 Underlying: Ordinary Shares · 1,417 shares Expires not disclosed F3 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F3 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F6 · derivative.exercise_date: Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period. All vested 2015 Performance Shares will be issued following the filing of the annual report on Form 10-K for the year ended December 31, 2017. F6 · derivative.expiration_date: Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period. All vested 2015 Performance Shares will be issued following the filing of the annual report on Form 10-K for the year ended December 31, 2017. Read SEC document
February 22, 2017 Filed Feb 24, 2017 22:58 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Exercise / conversion2014 Performance Shares · Derivative	11,641	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000006 · wf-form4_148797708545117.xml · derivative · entry 4 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 0 Underlying: Ordinary Shares · 11,641 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 Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F3 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F5 · derivative.exercise_date: Represents mandatory conversion into Issuer's Ordinary Shares of all 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer and filing of the annual report on Form 10-K for the year ended December 31, 2016. F5 · derivative.expiration_date: Represents mandatory conversion into Issuer's Ordinary Shares of all 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer and filing of the annual report on Form 10-K for the year ended December 31, 2016. Read SEC document
February 22, 2017 Filed Feb 24, 2017 22:58 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Grant2014 Performance Shares · Derivative	1,625	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000006 · wf-form4_148797708545117.xml · derivative · entry 3 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 11,641 Underlying: Ordinary Shares · 1,625 shares Expires not disclosed F3 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F3 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares. F4 · derivative.exercise_date: Represents 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2014 Performance Share award is tested annually over a three-year period. All vested 2014 Performance Shares are issued following the filing of the annual report on Form 10-K for the year ended December 31, 2016. F4 · derivative.expiration_date: Represents 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2014 Performance Share award is tested annually over a three-year period. All vested 2014 Performance Shares are issued following the filing of the annual report on Form 10-K for the year ended December 31, 2016. Read SEC document
February 22, 2017 Filed Feb 24, 2017 22:58 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	Tax withholdingOrdinary Shares	993	$56.25	$55,856.25	Disclosure SEC source: 0001561304-17-000006 · wf-form4_148797708545117.xml · nonDerivative · entry 2 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 50,229 F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Performance Shares. Read SEC document
February 22, 2017 Filed Feb 24, 2017 22:58 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantOrdinary Shares	11,641	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000006 · wf-form4_148797708545117.xml · nonDerivative · entry 1 Cain Michael · CIK 0001561304 · CEO, ABL & Group GC 10b5-1 filing: Not disclosed Ownership: Direct Disclosed balance after: 51,222 F1 · kind: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met. F1 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met. F1 · acquired: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met. Read SEC document
February 10, 2017 Filed Feb 13, 2017 16:44 UTC	ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774	GrantRestricted Share Units (2017 Grant) · Derivative	3,335	Not disclosed	Not disclosed	Disclosure SEC source: 0001561304-17-000004 · wf-form4_148700424047107.xml · derivative · entry 1 Cain Michael · CIK 0001561304 · CEO, ABL & 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 Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares. F1 · price: Each Restricted Share Unit represents the right to recieve one share of the Issuer's Ordinary Shares. F2 · derivative.exercise_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan. 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 recieved a number or Ordinary Shares equal to the number of Restricted Share Units then vesting. F2 · derivative.expiration_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan. 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 recieved a number or Ordinary Shares equal to the number of Restricted Share Units then vesting. Read SEC document

Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.