SKWD

SEC source: 0001937549-26-000002 · form4-01052026_090140.xml · derivative · entry 3

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,020 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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

F6 · derivative.exercise_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 2,020 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

F6 · derivative.expiration_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 2,020 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

SEC source: 0001937549-26-000002 · form4-01052026_090140.xml · nonDerivative · entry 2

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,915

F3 · 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.

F4 · 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: 0001937549-26-000002 · form4-01052026_090140.xml · nonDerivative · entry 1

Bodnar Dan PK · CIK 0001937549 · CHIEF INFORMATION OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,680

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.

F2 · balance_after: The number of securities reported reflects the June 1, 2025 acquisition of 152 shares and the December 1, 2025 acquisition of 168 shares of the Company's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively.

SEC source: 0001757909-26-000002 · form4-01052026_090137.xml · nonDerivative · entry 1

Hays James Charles · CIK 0001757909 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 174,061

F1 · kind: On January 1, 2026, the Issuer completed the acquisition of the entire issued share capital of Apollo Group Holdings Limited ("Apollo"). Pursuant to the terms of the Apollo Share Purchase Agreements, the consideration for the acquisition of Apollo was satisfied by the issuance of shares of Common Stock by the Issuer to the "Minority Sellers" and together with the "Majority Sellers", the "Sellers" with the remainder paid by the Issuer to the Sellers in cash.

F2 · shares: The Reporting Person was a Seller in the transaction and as such acquired 143,664 shares of Common Stock of the Issuer at a purchase price of $50.00 per share, in conjunction with the completion of the transaction

SEC source: 0001415833-26-000002 · form4-01052026_090146.xml · derivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 15,151 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 15,151 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 15,151 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

SEC source: 0001415833-26-000002 · form4-01052026_090146.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 74,447

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: 0001415833-26-000002 · form4-01052026_090146.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 80,420

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: 0001211319-26-000002 · form4-01052026_090140.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 3,787 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

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

F6 · derivative.exercise_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 3,787 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

F6 · derivative.expiration_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 3,787 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

SEC source: 0001211319-26-000002 · form4-01052026_090140.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,546

F3 · 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.

F4 · 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: 0001211319-26-000002 · form4-01052026_090140.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,047

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.

F2 · balance_after: The number of securities reported reflects the December 1, 2025 acquisition of 197 shares of the Issuer's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase period of June 1, 2025 through November 30, 2025.

SEC source: 0001937132-26-000002 · form4-01052026_090146.xml · derivative · entry 3

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,020 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 2,020 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 2,020 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

SEC source: 0001937132-26-000002 · form4-01052026_090146.xml · nonDerivative · entry 2

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,338

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: 0001937132-26-000002 · form4-01052026_090146.xml · nonDerivative · entry 1

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,079

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: 0001937316-26-000002 · form4-01052026_090134.xml · derivative · entry 3

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,525 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 2,525 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 2,525 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

SEC source: 0001937316-26-000002 · form4-01052026_090134.xml · nonDerivative · entry 2

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,480

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: 0001937316-26-000002 · form4-01052026_090134.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CPO, Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,484

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: 0001936023-26-000002 · form4-01052026_090118.xml · derivative · 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: 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.

F5 · 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 February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 3,619 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

F6 · derivative.expiration_date: On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 3,619 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.

SEC source: 0001936023-26-000002 · form4-01052026_090118.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: 24,362

F3 · 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.

F4 · 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: 0001936023-26-000002 · form4-01052026_090118.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: 25,797

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.

F2 · balance_after: The number of securities reported reflects the June 1, 2025 acquisition of 231 shares and the December 1, 2025 acquisition of 197 shares of the Company's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively.

SEC source: 0002102458-26-000003 · form4-01052026_090156.xml · nonDerivative · entry 2

Slaughter James Richard · CIK 0002102458 · CUO - Apollo · Division of Skyward Group

10b5-1 filing: No plan indicated

Ownership: Indirect · Hillside Family Trust 2025

Disclosed balance after: 12,724

F1 · kind: On January 1, 2026, the Issuer completed the acquisition of the entire issued share capital of Apollo Group Holdings Limited ("Apollo"). Pursuant to the terms of the Apollo Share Purchase Agreements, the consideration for the acquisition of Apollo was satisfied by the issuance of shares of Common Stock by the Issuer to the "Minority Sellers" and together with the "Majority Sellers", the "Sellers" with the remainder paid by the Issuer to the Sellers in cash.

F3 · shares: The Reporting Person is Trustee of Seller in the transaction and as such acquired 12,724 shares of Common Stock of the Issuer at a purchase price of $50.00 per share, in conjunction with the completion of the transaction.

F4 · ownership.nature: The Reporting Person is Trustee of the entity.

SEC source: 0002102458-26-000003 · form4-01052026_090156.xml · nonDerivative · entry 1

Slaughter James Richard · CIK 0002102458 · CUO - Apollo · Division of Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 55,475

F1 · kind: On January 1, 2026, the Issuer completed the acquisition of the entire issued share capital of Apollo Group Holdings Limited ("Apollo"). Pursuant to the terms of the Apollo Share Purchase Agreements, the consideration for the acquisition of Apollo was satisfied by the issuance of shares of Common Stock by the Issuer to the "Minority Sellers" and together with the "Majority Sellers", the "Sellers" with the remainder paid by the Issuer to the Sellers in cash.

F2 · shares: The Reporting Person was a Seller in the transaction and as such acquired 55,475 shares of Common Stock of the Issuer at a purchase price of $50.00 per share, in conjunction with the completion of the transaction.

SEC source: 0002102589-26-000004 · form4-01052026_090152.xml · nonDerivative · entry 1

McHarg Taryn Leonie · CIK 0002102589 · CFO - Apollo · Division of Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,764

F1 · kind: On January 1, 2026, the Issuer completed the acquisition of the entire issued share capital of Apollo Group Holdings Limited ("Apollo"). Pursuant to the terms of the Apollo Share Purchase Agreements, the consideration for the acquisition of Apollo was satisfied by the issuance of shares of Common Stock by the Issuer to the "Minority Sellers" and together with the "Majority Sellers", the "Sellers" with the remainder paid by the Issuer to the Sellers in cash

F2 · shares: The Reporting Person was a Seller in the transaction and as such acquired 7,764 shares of Common Stock of the Issuer at a purchase price of $50.00 per share, in conjunction with the completion of the transaction

SEC source: 0002101244-26-000003 · form4-01052026_090135.xml · nonDerivative · entry 2

Ibeson David Christopher Ben · CIK 0002101244 · CEO - Apollo · Division of Skyward Group

10b5-1 filing: No plan indicated

Ownership: Indirect · The Ibeson Family Trust

Disclosed balance after: 79,708

F1 · kind: On January 1, 2026, the Issuer completed the acquisition of the entire issued share capital of Apollo Group Holdings Limited ("Apollo"). Pursuant to the terms of the Apollo Share Purchase Agreements, the consideration for the acquisition of Apollo was satisfied by the issuance of shares of Common Stock by the Issuer to the "Minority Sellers" and together with the "Majority Sellers", the "Sellers" with the remainder paid by the Issuer to the Sellers in cash

F3 · shares: The Reporting Person is Trustee of Seller in the transaction and as such acquired 79,708 shares of Common Stock of the Issuer at a purchase price of $50.00 per share, in conjunction with the completion of the transaction.

F4 · ownership.nature: The Reporting Person is Trustee of the entity.

SEC source: 0002101244-26-000003 · form4-01052026_090135.xml · nonDerivative · entry 1

Ibeson David Christopher Ben · CIK 0002101244 · CEO - Apollo · Division of Skyward Group

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 266,867

F1 · kind: On January 1, 2026, the Issuer completed the acquisition of the entire issued share capital of Apollo Group Holdings Limited ("Apollo"). Pursuant to the terms of the Apollo Share Purchase Agreements, the consideration for the acquisition of Apollo was satisfied by the issuance of shares of Common Stock by the Issuer to the "Minority Sellers" and together with the "Majority Sellers", the "Sellers" with the remainder paid by the Issuer to the Sellers in cash

F2 · shares: The Reporting Person was a Seller in the transaction and as such acquired 266,867 shares of Common Stock of the Issuer at a purchase price of $50.00 per share, in conjunction with the completion of the transaction

SEC source: 0001937132-25-000005 · form4-12192025_041201.xml · nonDerivative · entry 1

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,059

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 8, 2025.

F2 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $50.00 - $50.10, inclusive (weighted average of $50.01052286). 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: 0001937132-25-000003 · form4-12162025_041201.xml · nonDerivative · entry 2

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 13,089

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 8, 2025.

SEC source: 0001937132-25-000003 · form4-12162025_041201.xml · nonDerivative · entry 1

Kapadia Sandip A · CIK 0001937132 · Head of Actuarial

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 14,289

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 8, 2025.

F2 · balance_after: The number of securities reported reflects the June 1, 2025 acquisition of 231 shares and the December 1, 2025 acquisition of 197 shares of the Company's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively.

SEC source: 0001937316-25-000003 · form4-12112025_101241.xml · nonDerivative · entry 1

Schmitt Thomas N · CIK 0001937316 · CHIEF PEOPLE & ADMIN.OFFICER

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 9,959

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

F2 · balance_after: The number of securities reported reflects the June 1, 2025 acquisition of 152 shares and the December 1, 2025 acquisition of 168 shares of the Company's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively.

SEC source: 0001415889-25-017515 · form4-06172025_040601.xml · nonDerivative · entry 2

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 123,063

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 12, 2025.

F4 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $58.98-$59.42, inclusive (weighted average of $59.06773394). 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: 0001415889-25-017515 · form4-06172025_040601.xml · nonDerivative · entry 1

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 133,629

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 12, 2025.

F2 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $58.34-$59.23, inclusive (weighted average of $58.76210199). 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.

F3 · balance_after: The number of securities reported reflects the June 6, 2025 acquisition of 231 shares of the Issuer's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase period of December 1, 2024 through May 31, 2025.

SEC source: 0001415889-25-016443 · form4-06102025_030601.xml · nonDerivative · entry 2

Robinson Andrew S · CIK 0001415833 · Director · CHAIRMAN & CEO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 65,269

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 10, 2024 and amended by the Reporting Person on March 6, 2025.

F3 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $63.3704-$63.62, inclusive (weighted average of $63.57540536). 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: 0001415889-25-016443 · form4-06102025_030601.xml · nonDerivative · entry 1

Robinson Andrew S · CIK 0001415833 · Director · CHAIRMAN & CEO

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 65,437

F1 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 10, 2024 and amended by the Reporting Person on March 6, 2025.

F2 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $62.365-$63.336, inclusive (weighted average of $62.64567893). 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: 0001415889-25-013162 · form4-05152025_080538.xml · nonDerivative · entry 1

Hill Kirby · CIK 0001935898 · Chairman, Captives & Programs

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,249

F1 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $60.8701-$60.91, inclusive (weighted average of $60.87225728). 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: 0001415889-25-012473 · form4-05092025_040514.xml · derivative · entry 4

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,779 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 RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F5 · derivative.exercise_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

F5 · derivative.expiration_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

SEC source: 0001415889-25-012473 · form4-05092025_040514.xml · nonDerivative · entry 1

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,903

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

SEC source: 0001415889-25-012472 · form4-05092025_040512.xml · derivative · entry 5

Hays James Charles · CIK 0001757909 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,779 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 RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F6 · derivative.exercise_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

F6 · derivative.expiration_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

SEC source: 0001415889-25-012472 · form4-05092025_040512.xml · nonDerivative · entry 1

Hays James Charles · CIK 0001757909 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 30,397

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

SEC source: 0001415889-25-012468 · form4-05092025_040503.xml · derivative · entry 3

Ashe Gena L · CIK 0001669943 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,779 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F4 · derivative.exercise_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

F4 · derivative.expiration_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

SEC source: 0001415889-25-012468 · form4-05092025_040503.xml · nonDerivative · entry 1

Ashe Gena L · CIK 0001669943 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,513

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

SEC source: 0001415889-25-012471 · form4-05092025_040510.xml · derivative · entry 3

Dall Marcia A · CIK 0001460624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,779 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F5 · derivative.exercise_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

F5 · derivative.expiration_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

SEC source: 0001415889-25-012471 · form4-05092025_040510.xml · nonDerivative · entry 1

Dall Marcia A · CIK 0001460624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,433

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

SEC source: 0001415889-25-012474 · form4-05092025_040516.xml · derivative · entry 3

Morrissey Michael J. · CIK 0001432033 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,779 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F5 · derivative.exercise_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

F5 · derivative.expiration_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

SEC source: 0001415889-25-012474 · form4-05092025_040516.xml · nonDerivative · entry 1

Morrissey Michael J. · CIK 0001432033 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,519

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

SEC source: 0001415889-25-012470 · form4-05092025_040508.xml · derivative · entry 3

Creager Robert E. · CIK 0001517566 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,779 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F4 · derivative.exercise_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

F4 · derivative.expiration_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

SEC source: 0001415889-25-012470 · form4-05092025_040508.xml · nonDerivative · entry 1

Creager Robert E. · CIK 0001517566 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 53,033

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

SEC source: 0001415889-25-012475 · form4-05092025_040519.xml · derivative · entry 3

Terry Katharine · CIK 0001936853 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,779 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F5 · derivative.exercise_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

F5 · derivative.expiration_date: On May 9, 2024, the Reporting Person was granted an RSU Award in the amount of 2,779 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 9, 2025.

SEC source: 0001415889-25-012475 · form4-05092025_040519.xml · nonDerivative · entry 1

Terry Katharine · CIK 0001936853 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,780

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

SEC source: 0001415889-25-012467 · form4-05092025_040501.xml · nonDerivative · entry 2

Robinson Andrew S · CIK 0001415833 · Director · CHAIRMAN & CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,540

F2 · kind: Sales to cover taxes and fees incurred in connection with the settlement of the Reporting Person's PSUs reported on this Form 4.

F3 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $58.565-$59.52, inclusive (weighted average of $59.23183338). 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: 0001415889-25-012476 · form4-05092025_040520.xml · nonDerivative · entry 2

HAUSHILL MARK W · CIK 0001211319 · EVP & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 186,146

F2 · kind: Sales to cover taxes and fees incurred in connection with the settlement of the Reporting Person's PSUs reported on this Form 4.

F3 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $58.565-$59.52, inclusive (weighted average of $59.23183338). 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: 0001415889-25-012473 · form4-05092025_040514.xml · derivative · entry 3

Kuczinski Anthony J · CIK 0001976607 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,797

Underlying: Common Stock · 1,797 shares

Expires not disclosed

F3 · derivative.exercise_price: Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F4 · derivative.exercise_date: On May 7, 2025, the Reporting Person was granted an RSU Award in the amount of 1,797 RSUs. Subject to the terms of the award agreement, this award will fully vest on May 7, 2026.

F4 · derivative.expiration_date: On May 7, 2025, the Reporting Person was granted an RSU Award in the amount of 1,797 RSUs. Subject to the terms of the award agreement, this award will fully vest on May 7, 2026.