BROWN DAVID A

SEC source: 0001394399-26-000011 · wk-form4_1788907997.xml · nonDerivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Leyton Ltd.

Disclosed balance after: 400,000

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 $36.00 to $36.47, 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 · ownership.nature: An investment holding company held by Thelwall Trust, a family trust established for the benefit of the reporting person and his family.

SEC source: 0001628280-26-047778 · wk-form4_1783627475.xml · nonDerivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,066

F1 · shares: Represents shares that have been surrendered to the Company to satisfy tax withholding and remittance obligations in connection with the net settlement of restricted stock units and does not represent a sale by the Reporting Person.

SEC source: 0001628280-26-043985 · wk-form4_1781730418.xml · derivative · entry 3

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,142

Underlying: Common Stock · 5,142 shares

Expires 2036-06-15

F3 · derivative.exercise_date: 2,571 of the shares subject to this option will vest on June 30, 2026, 1,285 of the shares subject to this option will vest on September 30, 2026 and the remaining 1,286 of the shares subject to this option will vest on December 31, 2026, subject to the Reporting Person's continued service to the Issuer or its subsidiaries through the applicable vesting date.

SEC source: 0001628280-26-043985 · wk-form4_1781730418.xml · nonDerivative · entry 2

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,237

F2 · shares: The amount represents RSUs that vest on the last business day immediately preceding the 2027 annual meeting of stockholders, subject to the reporting person's continued service to the Issuer through the vesting date.

SEC source: 0001628280-26-043985 · wk-form4_1781730418.xml · nonDerivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,267

F1 · shares: The amount represents restricted stock units ("RSUs") that fully vested on the date of grant. Each RSU represents a right to receive one share of the Issuer's common stock.

SEC source: 0001394399-26-000007 · wk-form4_1779311281.xml · nonDerivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Leyton Ltd.

Disclosed balance after: 450,000

F1 · shares: 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 $32.00 to $32.41, 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 · ownership.nature: An investment holding company held by Thelwall Trust, a family trust established for the benefit of the reporting person and his family.

SEC source: 0001394399-26-000004 · wk-form4_1779231033.xml · nonDerivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Leyton Ltd.

Disclosed balance after: 487,300

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 $31.52 to $32.09, 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 · ownership.nature: An investment holding company held by Thelwall Trust, a family trust established for the benefit of the reporting person and his family.

SEC source: 0001394399-26-000002 · wk-form4_1778194062.xml · nonDerivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 110,308

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 5, 2026, which was $30.43 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

F2 · balance_after: Includes restricted stock units.

SEC source: 0001628280-25-040791 · wk-form4_1755634019.xml · derivative · entry 6

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 278

Underlying: Common Stock · 278 shares

Expires 2031-05-31

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: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F2 · derivative.exercise_date: The options are fully vested.

SEC source: 0001628280-25-040791 · wk-form4_1755634019.xml · derivative · entry 5

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Nonvoting Common Stock · 278 shares

Expires 2031-08-31

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: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F1 · shares: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F2 · derivative.exercise_date: The options are fully vested.

SEC source: 0001628280-25-040791 · wk-form4_1755634019.xml · derivative · entry 4

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,500

Underlying: Common Stock · 7,500 shares

Expires 2031-05-31

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: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F1 · shares: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F2 · derivative.exercise_date: The options are fully vested.

SEC source: 0001628280-25-040791 · wk-form4_1755634019.xml · derivative · entry 3

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Nonvoting Common Stock · 7,500 shares

Expires 2031-07-31

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: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F1 · shares: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F2 · derivative.exercise_date: The options are fully vested.

SEC source: 0001628280-25-040791 · wk-form4_1755634019.xml · derivative · entry 2

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,750

Underlying: Common Stock · 18,750 shares

Expires 2031-05-31

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: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F1 · shares: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F2 · derivative.exercise_date: The options are fully vested.

SEC source: 0001628280-25-040791 · wk-form4_1755634019.xml · derivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Nonvoting Common Stock · 18,750 shares

Expires 2031-05-31

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: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F1 · shares: The options were granted initially as the right to buy Nonvoting Common Stock. On the closing date of the initial public offering, these converted to the right to buy Common Stock instead of Nonvoting Common Stock, for the same price and under the same conditions.

F2 · derivative.exercise_date: The options are fully vested.

SEC source: 0001593275-25-000178 · wk-form4_1747686622.xml · nonDerivative · entry 2

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 105,379

F2 · shares: Represents an annual grant of RSUs awarded to the reporting person pursuant to the Company's Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on May 15, 2025, which was $20.87 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

F3 · balance_after: Includes RSUs.

SEC source: 0001593275-25-000178 · wk-form4_1747686622.xml · nonDerivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 98,192

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") awarded to the reporting person pursuant to the Hamilton Insurance Group, Ltd. (the "Company") Non-Employee Director Compensation Program. The number of RSUs was determined based on a target grant value of $150,000 and the closing price of the Company's common shares on June 12, 2024, which was $16.75 per share. The RSUs cliff vest on the earlier of the one-year anniversary of the grant date or the date of the subsequent annual general meeting.

SEC source: 0001140361-24-011527 · form4.xml · nonDerivative · entry 1

BROWN DAVID A · CIK 0001394399 · Director · Chairman of the Board

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 89,237

F1 · shares: The number of shares delivered to the reporting person relating to a portion of the compensation paid to the reporting person in the amount of $37,500 for service on the Board of Directors of the issuer from July 1, 2023 through December 31, 2023.

F2 · price: The value of the shares at the end of the period of service by the reporting person which was used to determine the number of shares to be delivered to the reporting person.