SKWD

SEC source: 0001936023-26-000006 · form4-02272026_040205.xml · derivative · entry 5

Burkhart John A III · CIK 0001936023 · President, US P&C

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,210

Underlying: Common Stock · 7,210 shares

Expires not disclosed

F7 · derivative.exercise_price: On February 25, 2026, the Reporting Person was granted 7,210 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

F7 · derivative.exercise_date: On February 25, 2026, the Reporting Person was granted 7,210 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

F7 · derivative.expiration_date: On February 25, 2026, the Reporting Person was granted 7,210 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

SEC source: 0001936023-26-000006 · form4-02272026_040205.xml · derivative · entry 4

Burkhart John A III · CIK 0001936023 · President, US P&C

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,210

Underlying: Common Stock · 7,210 shares

Expires not disclosed

F5 · derivative.exercise_price: Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 7,210 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029.

F6 · derivative.expiration_date: On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 7,210 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029.

SEC source: 0001936023-26-000006 · form4-02272026_040205.xml · derivative · entry 3

Burkhart John A III · CIK 0001936023 · President, US P&C

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 3,619 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 PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F4 · derivative.exercise_date: On February 27, 2023, the Reporting Person was awarded 3,619 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

F4 · derivative.expiration_date: On February 27, 2023, the Reporting Person was awarded 3,619 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

SEC source: 0001936023-26-000006 · form4-02272026_040205.xml · nonDerivative · entry 1

Burkhart John A III · CIK 0001936023 · President, US P&C

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 36,469

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of Table II.

SEC source: 0001937316-26-000006 · form4-02102026_040201.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 14,747

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 11, 2025.

F2 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $43.15-$43.78, inclusive (weighted average of $43.49167813). Reporting Person undertakes to provide to issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within ranges set forth herein.

SEC source: 0001936008-26-000004 · form4-01142026_100132.xml · derivative · entry 6

Duffy Sean W · CIK 0001936008 · EVP & Chief Claims Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

F6 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

SEC source: 0001936008-26-000004 · form4-01142026_100132.xml · derivative · entry 5

Duffy Sean W · CIK 0001936008 · EVP & Chief Claims Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,000

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

F5 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

SEC source: 0001936008-26-000004 · form4-01142026_100132.xml · nonDerivative · entry 4

Duffy Sean W · CIK 0001936008 · EVP & Chief Claims Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,036

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001936008-26-000004 · form4-01142026_100132.xml · nonDerivative · entry 3

Duffy Sean W · CIK 0001936008 · EVP & Chief Claims Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,131

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001936008-26-000004 · form4-01142026_100132.xml · nonDerivative · entry 2

Duffy Sean W · CIK 0001936008 · EVP & Chief Claims Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,131

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001936008-26-000004 · form4-01142026_100132.xml · nonDerivative · entry 1

Duffy Sean W · CIK 0001936008 · EVP & Chief Claims Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,407

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001937549-26-000004 · form4-01142026_100112.xml · derivative · entry 6

Bodnar Dan PK · CIK 0001937549 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

F6 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

SEC source: 0001937549-26-000004 · form4-01142026_100112.xml · derivative · entry 5

Bodnar Dan PK · CIK 0001937549 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,000

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

F5 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

SEC source: 0001937549-26-000004 · form4-01142026_100112.xml · nonDerivative · entry 4

Bodnar Dan PK · CIK 0001937549 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,998

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001937549-26-000004 · form4-01142026_100112.xml · nonDerivative · entry 3

Bodnar Dan PK · CIK 0001937549 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 26,866

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001937549-26-000004 · form4-01142026_100112.xml · nonDerivative · entry 2

Bodnar Dan PK · CIK 0001937549 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,866

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001937549-26-000004 · form4-01142026_100112.xml · nonDerivative · entry 1

Bodnar Dan PK · CIK 0001937549 · Chief Information Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,915

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001415833-26-000006 · form4-01142026_100140.xml · derivative · entry 6

Robinson Andrew S · CIK 0001415833 · Director · Chairman & CEO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 50,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 100,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

F6 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 100,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

SEC source: 0001415833-26-000006 · form4-01142026_100140.xml · derivative · entry 5

Robinson Andrew S · CIK 0001415833 · Director · Chairman & CEO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 50,000

Underlying: Common Stock · 50,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 100,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

F5 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 100,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

SEC source: 0001415833-26-000006 · form4-01142026_100140.xml · nonDerivative · entry 4

Robinson Andrew S · CIK 0001415833 · Director · Chairman & CEO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 134,915

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001415833-26-000006 · form4-01142026_100140.xml · nonDerivative · entry 3

Robinson Andrew S · CIK 0001415833 · Director · Chairman & CEO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 154,590

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001415833-26-000006 · form4-01142026_100140.xml · nonDerivative · entry 2

Robinson Andrew S · CIK 0001415833 · Director · Chairman & CEO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 104,590

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001415833-26-000006 · form4-01142026_100140.xml · nonDerivative · entry 1

Robinson Andrew S · CIK 0001415833 · Director · Chairman & CEO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 124,447

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001211319-26-000004 · form4-01142026_090141.xml · derivative · entry 6

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 6,665 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

F6 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

SEC source: 0001211319-26-000004 · form4-01142026_090141.xml · derivative · entry 5

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,665

Underlying: Common Stock · 6,665 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

F5 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

SEC source: 0001211319-26-000004 · form4-01142026_090141.xml · nonDerivative · entry 4

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 133,456

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001211319-26-000004 · form4-01142026_090141.xml · nonDerivative · entry 3

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,079

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001211319-26-000004 · form4-01142026_090141.xml · nonDerivative · entry 2

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 129,414

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001211319-26-000004 · form4-01142026_090141.xml · nonDerivative · entry 1

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 132,211

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · derivative · entry 6

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

F6 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · derivative · entry 5

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,000

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

F5 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · nonDerivative · entry 4

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,363

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · nonDerivative · entry 3

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,331

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.

F1 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · nonDerivative · entry 2

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,331

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001937316-26-000004 · form4-01142026_100152.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,480

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001937132-26-000004 · form4-01142026_100102.xml · derivative · entry 6

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

F6 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

SEC source: 0001937132-26-000004 · form4-01142026_100102.xml · derivative · entry 5

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,000

Underlying: Common Stock · 5,000 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

F5 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

SEC source: 0001937132-26-000004 · form4-01142026_100102.xml · nonDerivative · entry 4

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,545

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001937132-26-000004 · form4-01142026_100102.xml · nonDerivative · entry 3

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,353

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001937132-26-000004 · form4-01142026_100102.xml · nonDerivative · entry 2

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,353

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001937132-26-000004 · form4-01142026_100102.xml · nonDerivative · entry 1

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,338

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001936023-26-000004 · form4-01142026_100105.xml · derivative · entry 6

Burkhart John A III · CIK 0001936023 · President, US P&C, Skyward Grp

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 6,665 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F6 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

F6 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

SEC source: 0001936023-26-000004 · form4-01142026_100105.xml · derivative · entry 5

Burkhart John A III · CIK 0001936023 · President, US P&C, Skyward Grp

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,665

Underlying: Common Stock · 6,665 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

F5 · derivative.expiration_date: On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.

SEC source: 0001936023-26-000004 · form4-01142026_100105.xml · nonDerivative · entry 4

Burkhart John A III · CIK 0001936023 · President, US P&C, Skyward Grp

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,271

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001936023-26-000004 · form4-01142026_100105.xml · nonDerivative · entry 3

Burkhart John A III · CIK 0001936023 · President, US P&C, Skyward Grp

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 34,894

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001936023-26-000004 · form4-01142026_100105.xml · nonDerivative · entry 2

Burkhart John A III · CIK 0001936023 · President, US P&C, Skyward Grp

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 28,229

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001936023-26-000004 · form4-01142026_100105.xml · nonDerivative · entry 1

Burkhart John A III · CIK 0001936023 · President, US P&C, Skyward Grp

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 31,027

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.

SEC source: 0001936008-26-000002 · form4-01052026_090133.xml · derivative · entry 3

Duffy Sean W · CIK 0001936008 · EVP & CHIEF CLAIMS OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,861 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.

F4 · derivative.exercise_price: Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F5 · derivative.exercise_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 2,861 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

F5 · derivative.expiration_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 2,861 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

SEC source: 0001936008-26-000002 · form4-01052026_090133.xml · nonDerivative · entry 2

Duffy Sean W · CIK 0001936008 · EVP & CHIEF CLAIMS OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,407

F2 · kind: The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

F3 · price: The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock for the trading day immediately preceding the vesting date, December 31, 2025, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.

SEC source: 0001936008-26-000002 · form4-01052026_090133.xml · nonDerivative · entry 1

Duffy Sean W · CIK 0001936008 · EVP & CHIEF CLAIMS OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,674

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 · shares: Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.