HG

SEC source: 0001140361-24-011529 · form4.xml · derivative · entry 2

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 2,793 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 8,380 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 8,380 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011529 · form4.xml · nonDerivative · entry 1

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 38,798

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: 0001140361-24-011523 · 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: 0001140361-24-011534 · form4.xml · derivative · entry 4

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,408

Underlying: Class B Common Shares · 10,204 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 30,612 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 30,612 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011534 · form4.xml · derivative · entry 3

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,872

Underlying: Class B Common Shares · 7,872 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 23,617 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 23,617 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011534 · form4.xml · derivative · entry 2

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 12,957 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 38,873 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 38,873 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011534 · form4.xml · nonDerivative · entry 1

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 84,822

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: 0001140361-24-011530 · form4.xml · nonDerivative · entry 1

Karna Anu · CIK 0001942191 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 941

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 $14,063 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.

SEC source: 0001140361-24-011533 · form4.xml · nonDerivative · entry 1

Pestcoe Marvin · CIK 0001499968 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 47,477

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.

SEC source: 0001140361-24-011531 · form4.xml · nonDerivative · entry 1

Gauthier John J · CIK 0001456268 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,941

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 $14,063 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.

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.

SEC source: 0001140361-24-011526 · form4.xml · derivative · entry 4

Howie Craig · CIK 0001549925 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 29,155

Underlying: Class B Common Shares · 14,577 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F5 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 43,732 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F5 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 43,732 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011526 · form4.xml · derivative · entry 3

Howie Craig · CIK 0001549925 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 10,121

Underlying: Class B Common Shares · 10,121 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 30,364 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F4 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 30,364 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011526 · form4.xml · nonDerivative · entry 1

Howie Craig · CIK 0001549925 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 31,277

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 · price: RSUs convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011540 · form4.xml · nonDerivative · entry 1

Freda William C · CIK 0001626695 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 47,194

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 $51,000 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.

SEC source: 0001140361-24-011539 · form4.xml · derivative · entry 5

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,377

Underlying: Class B Common Shares · 3,189 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F6 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 9,566 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F6 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 9,566 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011539 · form4.xml · derivative · entry 4

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,429

Underlying: Class B Common Shares · 2,429 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F5 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 7,287 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F5 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 7,287 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011539 · form4.xml · derivative · entry 3

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 2,264 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 6,794 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

F4 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 6,794 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011539 · form4.xml · nonDerivative · entry 1

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,331

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 · price: RSUs convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011536 · form4.xml · nonDerivative · entry 1

Richards Doreen Pauline Elizabeth · CIK 0001999780 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 113,054

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.

SEC source: 0001140361-24-011521 · form4.xml · derivative · entry 5

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,625

Underlying: Class B Common Shares · 6,812 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F6 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 20,437 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F6 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 20,437 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011521 · form4.xml · derivative · entry 4

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,322

Underlying: Class B Common Shares · 5,321 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F5 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 15,965 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F5 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 15,965 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011521 · form4.xml · derivative · entry 3

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 4,815 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 14,445 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

F4 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 14,445 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011521 · form4.xml · nonDerivative · entry 1

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 93,869

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 · price: RSUs convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011524 · form4.xml · nonDerivative · entry 1

Simmons Everard Barclay · CIK 0001999727 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,881

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 $28,125 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.

SEC source: 0001140361-24-011520 · form4.xml · derivative · entry 5

Baker Alexander James · CIK 0001999736 · Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,790

Underlying: Class B Common Shares · 4,395 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F6 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 13,185 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F6 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 13,185 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011520 · form4.xml · derivative · entry 4

Baker Alexander James · CIK 0001999736 · Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,556

Underlying: Class B Common Shares · 5,555 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F5 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 16,667 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F5 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 16,667 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011520 · form4.xml · derivative · entry 3

Baker Alexander James · CIK 0001999736 · Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 6,190 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: RSUs convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 18,572 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

F4 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 18,572 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011520 · form4.xml · nonDerivative · entry 1

Baker Alexander James · CIK 0001999736 · Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 49,935

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 · price: RSUs convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011528 · form4.xml · nonDerivative · entry 2

Fisher Daniel Mark · CIK 0001999653 · Group Head of HR & Comm.

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,171

F1 · shares: Represents shares retained by the issuer to satisfy tax withholding obligations upon the vesting of restricted stock units ("RSUs").

F2 · price: Represents the value of the shares on the vesting date which was used to determine the number of shares to be retained by the issuer to satisfy the tax withholding obligations.

SEC source: 0001140361-24-011522 · form4.xml · nonDerivative · entry 2

Kuchma Anita Breslin · CIK 0001999605 · CEO, Hamilton Select

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,725

F1 · shares: Represents shares retained by the issuer to satisfy tax withholding obligations upon the vesting of restricted stock units ("RSUs").

F2 · price: Represents the value of the shares on the vesting date which was used to determine the number of shares to be retained by the issuer to satisfy the tax withholding obligations.

SEC source: 0001140361-24-011535 · form4.xml · nonDerivative · entry 2

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 467,500

F1 · shares: Represents shares retained by the issuer to satisfy tax withholding obligations upon the vesting of restricted stock units ("RSUs").

F2 · price: Represents the value of the shares on the vesting date which was used to determine the number of shares to be retained by the issuer to satisfy the tax withholding obligations.

SEC source: 0001140361-24-011526 · form4.xml · nonDerivative · entry 2

Howie Craig · CIK 0001549925 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 19,934

F1 · shares: Represents shares retained by the issuer to satisfy tax withholding obligations upon the vesting of restricted stock units ("RSUs").

F2 · price: Represents the value of the shares on the vesting date which was used to determine the number of shares to be retained by the issuer to satisfy the tax withholding obligations.

SEC source: 0001140361-24-011539 · form4.xml · nonDerivative · entry 2

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,541

F1 · shares: Represents shares retained by the issuer to satisfy tax withholding obligations upon the vesting of restricted stock units ("RSUs").

F2 · price: Represents the value of the shares on the vesting date which was used to determine the number of shares to be retained by the issuer to satisfy the tax withholding obligations.

SEC source: 0001140361-24-011521 · form4.xml · nonDerivative · entry 2

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 85,904

F1 · shares: Represents shares retained by the issuer to satisfy tax withholding obligations upon the vesting of restricted stock units ("RSUs").

F2 · price: Represents the value of the shares on the vesting date which was used to determine the number of shares to be retained by the issuer to satisfy the tax withholding obligations.

SEC source: 0001140361-24-011520 · form4.xml · nonDerivative · entry 2

Baker Alexander James · CIK 0001999736 · Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 42,350

F1 · shares: Represents shares retained by the issuer to satisfy tax withholding obligations upon the vesting of restricted stock units ("RSUs").

F2 · price: Represents the value of the shares on the vesting date which was used to determine the number of shares to be retained by the issuer to satisfy the tax withholding obligations.

SEC source: 0001140361-24-000272 · form4.xml · derivative · entry 1

Bernhard Keith Donald · CIK 0001999608 · Group Chief Audit Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,788

Underlying: Class B Common Shares · 11,788 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.

SEC source: 0001140361-24-000260 · form4.xml · derivative · entry 1

Cundliffe Chad Allan · CIK 0001999638 · Group Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,049

Underlying: Class B Common Shares · 37,049 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.

SEC source: 0001140361-24-000277 · form4.xml · derivative · entry 1

Fisher Daniel Mark · CIK 0001999653 · Group Head of HR & Comm.

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 58,942

Underlying: Class B Common Shares · 58,942 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.

SEC source: 0001140361-24-000266 · form4.xml · derivative · entry 1

Kuchma Anita Breslin · CIK 0001999605 · CEO, Hamilton Select

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 58,942

Underlying: Class B Common Shares · 58,942 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.

SEC source: 0001140361-24-000259 · form4.xml · derivative · entry 1

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 303,133

Underlying: Class B Common Shares · 303,133 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.

SEC source: 0001140361-24-000275 · form4.xml · derivative · entry 1

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel & Sec.

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 58,942

Underlying: Class B Common Shares · 58,942 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.

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.

SEC source: 0001140361-24-000257 · form4.xml · derivative · entry 1

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 67,362

Underlying: Class B Common Shares · 67,362 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.

SEC source: 0001140361-24-000264 · form4.xml · derivative · entry 1

Howie Craig · CIK 0001549925 · Group Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,044

Underlying: Class B Common Shares · 101,044 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.

SEC source: 0001140361-24-000270 · form4.xml · derivative · entry 1

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 50,522

Underlying: Class B Common Shares · 50,522 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.

SEC source: 0001140361-24-000268 · form4.xml · derivative · entry 1

Baker Alexander James · CIK 0001999736 · Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 58,942

Underlying: Class B Common Shares · 58,942 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.