SKWD · Skyward Specialty Insurance Group, Inc. · Insider Trading

Each Restricted Stock Unit ("RSU") represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

On August 6, 2026, the Reporting Person was granted an RSU Award in the amount of 1,845 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $51.30-$51.415, inclusive (weighted average of $51.3235). 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.

The number of securities reported reflects the June 5, 2026 acquisition of 191 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 period of December 1, 2025 through May 31, 2026.

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

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 RSU Agreement, this award fully vested on May 7, 2026.

The Reporting Person elected to sell shares to cover the associated tax liability incurred due to the vesting and settlement of the RSUs reported on this Form 4.The Issuer delayed the settlement, pursuant to the terms of the RSU Award Agreement, so that the sales to cover the tax liability occurred during an open trading window.

Sales to cover taxes and fees incurred in connection with the vesting and settlement of the Reporting Person's RSUs reported on this Form 4.

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

Sales to cover taxes and fees incurred in connection with the vesting and settlement of the Reporting Person's RSUs reported on this Form 4.

Sales to cover taxes and fees incurred in connection with the vesting and settlement of the Reporting Person's RSUs reported on this Form 4.

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

Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

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 RSU Agreement, this award fully vested on May 7, 2026.

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

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.

Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

On February 27, 2023, the Reporting Person was awarded 3,787 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.

Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

The Reporting Person has elected to defer the settlement of this RSU award until their separation from the Company, pursuant to the Issuer's Deferred Compensation Plan for Non-Employee Directors.

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.

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.

Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

On February 27, 2023, the Reporting Person was awarded 2,020 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.

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

Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

The Reporting Person has elected to defer the settlement of this RSU award until their separation from the Company, pursuant to the Issuer's Deferred Compensation Plan for Non-Employee Directors.

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.

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.

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.

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.

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

Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

On February 27, 2023, the Reporting Person was awarded 2,525 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.

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

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

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

Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

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

Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

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.

Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

On February 27, 2023, the Reporting Person was awarded 2,861 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.

Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,890 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

On February 27, 2023, the Reporting Person was awarded 2,020 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.

Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

On February 27, 2023, the Reporting Person was awarded 15,151 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.

Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

On May 7, 2025, the Reporting Person was granted an RSU award of 1,797 RSUs. Subject to the terms of the award agreement, and pursuant to Board-approved accelerated vesting to coincide with the Reporting Person's director term ending at the Company's 2026 Annual Meeting of Shareholders, this award fully vested on May 5, 2026.

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

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

Each RSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

On May 7, 2025, the Reporting Person was granted an RSU award of 1,797 RSUs. Subject to the terms of the award agreement, and pursuant to Board-approved accelerated vesting to coincide with the Reporting Person's director term ending at the Company's 2026 Annual Meeting of Shareholders, this award fully vested on May 5, 2026.

Prices reported in Column 4 are weighted average prices. Shares were purchased in multiple transactions at prices ranging from $45.75-$46.74, inclusive (weighted average of $46.57). Reporting Person undertakes to provide to Issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth herein.