Deegan Brian John

SEC source: 0001999604-26-000004 · wk-form4_1778194079.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 71,347

F1 · price: The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $30.57 to $30.92, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

F2 · balance_after: Includes restricted stock units.

SEC source: 0001999604-26-000002 · wk-form4_1772663452.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 82,347

F1 · shares: Represents a grant of restricted stock units ("RSUs") pursuant to the Hamilton Insurance Group, Ltd. Equity Incentive Plan. Each RSU represents a contingent right to receive one share of Class B common shares upon vesting. The RSUs vest in three equal annual installments beginning on March 1, 2027, subject to the reporting person's continued service through each vesting date.

F2 · balance_after: Includes restricted stock units.

F3 · balance_after: Total reflects rounding adjustments and has been updated accordingly.

SEC source: 0001593275-25-000044 · wk-form4_1740792748.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,807

F1 · balance_after: The reported transaction involved the reporting person's receipt of a grant of 13,689 restricted stock units ("RSUs") under the Hamilton Insurance Group, Ltd. ("HG") Equity Incentive Plan which vest one third per year on March 1, 2026, 2027 and 2028 respectively. Each RSU represents a contingent right to receive one share of HG Class B Common Shares upon vesting. The total reported in Column 5 includes the 13,689 newly awarded and unvested RSUs, 41,848 unvested RSUs previously reported in Table I and Table II and 13,270 Common Shares.

SEC source: 0001593275-25-000114 · wk-form4a_1743026216.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 71,088

F1 · shares: On February 28, 2025, the reporting person filed a Form 4 which incorrectly stated the reporting person's receipt of a grant of 13,689 restricted stock units ("RSUs") under the Hamilton Insurance Group, Ltd. ("HG") Equity Incentive Plan. This amendment on Form 4/A is being filed to correct this error. The corrected transaction involved the reporting person's receipt of a grant of 15,970 RSUs which vest one third per year on March 1, 2026, 2027 and 2028 respectively. Each RSU represents a contingent right to receive one share of HG Class B Common Shares upon vesting.

F2 · balance_after: Includes common shares and restricted stock units as of the filing date of this amendment.

SEC source: 0001140361-25-000162 · form4.xml · derivative · entry 3

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,102

Underlying: Class B Common Shares · 5,102 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.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") converts into Class B Common Shares on a one-for-one-basis.

F4 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 15,306 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F4 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 15,306 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-25-000162 · form4.xml · derivative · entry 2

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 4,723 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.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") converts into Class B Common Shares on a one-for-one-basis.

F3 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 14,170 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F3 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 14,170 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-25-000162 · form4.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 30,649

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.

F1 · price: Each restricted stock unit ("RSU") converts into Class B Common Shares on a one-for-one-basis.

F2 · balance_after: Includes RSU's previously reported in Table I.

SEC source: 0001140361-24-047992 · form4.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,824

F1 · price: The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $19.06 to $19.325, inclusive. The Reporting Person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

F2 · balance_after: Includes RSU's previously reported in Table I.

SEC source: 0001140361-24-046544 · form4.xml · derivative · entry 2

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,367

Underlying: Class B Common Shares · 19,367 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.

F1 · derivative.exercise_price: Each restricted stock unit ("RSU") converts into Class B Common Shares on a one-for-one-basis.

F3 · derivative.exercise_date: On December 19, 2023, the reporting person was issued 38,733 restricted stock units ("RSU's") that vest 50% on November 10, 2024 and 50% on 10 November 2025, subject to the terms of The Hamilton Insurance Group, Ltd. Value Appreciation Pool Rules.

F3 · derivative.expiration_date: On December 19, 2023, the reporting person was issued 38,733 restricted stock units ("RSU's") that vest 50% on November 10, 2024 and 50% on 10 November 2025, subject to the terms of The Hamilton Insurance Group, Ltd. Value Appreciation Pool Rules.

SEC source: 0001140361-24-046544 · form4.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 38,324

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.

F1 · price: Each restricted stock unit ("RSU") converts into Class B Common Shares on a one-for-one-basis.

F2 · balance_after: Includes RSU's previously reported in Table I.

SEC source: 0001140361-24-026921 · form4.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,957

F1 · price: The price reported in Column 4 represents a weighted average price. These Class B common shares were sold in multiple transactions at prices ranging from $16.65 to $16.75, inclusive. The Reporting Person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

F2 · balance_after: The total reported in Column 5 represents 17,379 awards of restricted stock units granted on March 5, 2024 and previously reported in Table I of Form 4 and 1,578 Class B common shares. This total does not include 53,660 awards of restricted stock units granted prior to 2024 and previously reported in Table II of Form 4.

SEC source: 0001140361-24-012054 · form4.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,957

F1 · price: On March 5, 2024, the reporting person was granted 17,379 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share.

SEC source: 0001140361-24-011523 · form4.xml · derivative · entry 4

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,204

Underlying: Class B Common Shares · 5,102 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.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 15,306 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F4 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 15,306 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011523 · form4.xml · derivative · entry 3

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,723

Underlying: Class B Common Shares · 4,723 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.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F3 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 14,170 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F3 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 14,170 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011523 · form4.xml · derivative · entry 2

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 3,460 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.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F2 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 10,380 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

F2 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 10,380 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011523 · form4.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,578

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.

F1 · price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-000279 · form4.xml · derivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 38,733

Underlying: Class B Common Shares · 38,733 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a right to receive one Class B common share.

F2 · derivative.exercise_date: The restricted stock units vest 50% on 10 November 2024 and 50% on 10 November 2025, subject to the terms of The Hamilton Insurance Group, Ltd. Value Appreciation Pool Rules. The number reported here reflects the restricted stock units outstanding subject to future vesting.

F2 · derivative.expiration_date: The restricted stock units vest 50% on 10 November 2024 and 50% on 10 November 2025, subject to the terms of The Hamilton Insurance Group, Ltd. Value Appreciation Pool Rules. The number reported here reflects the restricted stock units outstanding subject to future vesting.