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person · Reporting owner

Robinson Andrew S

Disclosed activity across 2 companies

Tapewire entity
48687
SEC CIK
0001415833

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
CRAWFORD & COCRDA CRDB · Entity 1463Executive Vice PresidentFebruary 08, 2017April 07, 2017
Skyward Specialty Insurance Group, Inc.SKWD · Entity 4400Director · Chairman & CEO, Skyward GroupMay 06, 2026May 08, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

CRAWFORD & CO

Report date February 08, 2017 · Filed April 07, 2017

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Employee Stock Option (right to buy)SEC Table II · derivative / convertible security · Conversion / exercise price $9.22 · Expires 2027-02-08Direct39,511 Reported balance After 2017-02-08 transaction · row 1 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 1 · 2017-02-08 · Grant · Acquired 39,511 · Balance 39,511

F1: Option becomes exercisable as to approximately 1/3 of original number of shares annually commencing on date indicated.

Filing footnotes · ownership attribution and instrument terms

F1: Option becomes exercisable as to approximately 1/3 of original number of shares annually commencing on date indicated.

Skyward Specialty Insurance Group, Inc.

Report date May 06, 2026 · Filed May 08, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect179,894 Ending reported balance After 2026-05-06 transaction · row 2
2 source rows · reconciled sequence

Row 1 · 2026-05-06 · Exercise / conversion · Acquired 20,150 · Balance 187,824

F1: 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.

Row 2 · 2026-05-06 · Tax withholding · Disposed 7,930 · Balance 179,894

F2: 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.

2023 LTIP - PSUsSEC Table II · derivative / convertible securityDirect0 Reported balance After 2026-05-06 transaction · row 3 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 3 · 2026-05-06 · Exercise / conversion · Disposed 15,151 · Balance 0

F3: Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F4: 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.

Filing footnotes · ownership attribution and instrument terms

F1: 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.

F2: 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.

F3: Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

F4: 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.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
May 06, 2026 Filed May 8, 2026 20:46 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 LTIP - PSUs · Derivative 15,151 $0.00 $0.00
Disclosure

SEC source: 0001415833-26-000012 · form4-05082026_080524.xml · derivative · entry 3

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 · 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.

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 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.

F4 · derivative.expiration_date: 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.

Read SEC document
May 06, 2026 Filed May 8, 2026 20:46 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 7,930 $43.68 $346,382.40
Disclosure

SEC source: 0001415833-26-000012 · form4-05082026_080524.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: 179,894

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 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.

Read SEC document
May 06, 2026 Filed May 8, 2026 20:46 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 20,150 $0.00 $0.00
Disclosure

SEC source: 0001415833-26-000012 · form4-05082026_080524.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: 187,824

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.

Read SEC document
February 27, 2026 Filed Feb 27, 2026 21:56 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 PurchaseCommon Stock 11,279 $46.94 $529,436.26
Disclosure

SEC source: 0001415833-26-000010 · form4-02272026_090236.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: 167,674

F2 · price: Prices reported in Column 4 are weighted average prices. Shares were purchased in multiple transactions at prices ranging from $46.75-$47.32, inclusive (weighted average of $46.94). 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.

Read SEC document
February 27, 2026 Filed Feb 27, 2026 21:56 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 PurchaseCommon Stock 10,821 $46.57 $503,933.97
Disclosure

SEC source: 0001415833-26-000010 · form4-02272026_090236.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: 156,395

F1 · price: 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.

Read SEC document
February 26, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 6,916 $45.89 $317,375.24
Disclosure

SEC source: 0001415833-26-000008 · form4-02272026_040201.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: 145,574

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 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.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2026 LTIP - PSUs · Derivative 28,841 $0.00 $0.00
Disclosure

SEC source: 0001415833-26-000008 · form4-02272026_040201.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: 28,841

Underlying: Common Stock · 28,841 shares

Expires not disclosed

F8 · derivative.exercise_price: On February 25, 2026, the Reporting Person was granted 28,841 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.

F8 · derivative.exercise_date: On February 25, 2026, the Reporting Person was granted 28,841 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.

F8 · derivative.expiration_date: On February 25, 2026, the Reporting Person was granted 28,841 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.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2026 LTIP - PSUs · Derivative 28,841 $0.00 $0.00
Disclosure

SEC source: 0001415833-26-000008 · form4-02272026_040201.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: 28,841

Underlying: Common Stock · 28,841 shares

Expires not disclosed

F7 · derivative.exercise_price: On February 25, 2026, the Reporting Person was granted 28,841 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 28,841 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 28,841 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.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2026 LTIP - RSUs · Derivative 28,841 $0.00 $0.00
Disclosure

SEC source: 0001415833-26-000008 · form4-02272026_040201.xml · derivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 28,841

Underlying: Common Stock · 28,841 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 28,841 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 28,841 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 LTIP - PSUs · Derivative 15,151 $0.00 $0.00
Disclosure

SEC source: 0001415833-26-000008 · form4-02272026_040201.xml · derivative · entry 3

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 · 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.

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 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.

F4 · derivative.expiration_date: 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.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 17,575 $0.00 $0.00
Disclosure

SEC source: 0001415833-26-000008 · form4-02272026_040201.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: 152,490

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.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:03 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 IPO RSU Grant (3-Year) · Derivative 50,000 $0.00 $0.00
Disclosure

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.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:03 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 IPO RSU Grant (4-Year) · Derivative 50,000 $0.00 $0.00
Disclosure

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.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:03 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 19,675 $46.10 $907,017.50
Disclosure

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.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:03 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 50,000 $0.00 $0.00
Disclosure

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.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:03 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 19,857 $46.10 $915,407.70
Disclosure

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.

Read SEC document
January 12, 2026 Filed Jan 14, 2026 22:03 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 50,000 $0.00 $0.00
Disclosure

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.

Read SEC document
January 01, 2026 Filed Jan 5, 2026 21:35 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 LTIP - RSUs · Derivative 15,151 $0.00 $0.00
Disclosure

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.

Read SEC document
January 01, 2026 Filed Jan 5, 2026 21:35 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Tax withholdingCommon Stock 5,973 $51.11 $305,280.03
Disclosure

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.

Read SEC document
January 01, 2026 Filed Jan 5, 2026 21:35 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 15,151 $0.00 $0.00
Disclosure

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.

Read SEC document
June 06, 2025 Filed Jun 10, 2025 19:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 168 $63.58 $10,680.67
Disclosure

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.

Read SEC document
June 06, 2025 Filed Jun 10, 2025 19:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 36,103 $62.65 $2,261,694.10
Disclosure

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.

Read SEC document
May 08, 2025 Filed May 9, 2025 20:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 13,786 $59.23 $816,569.59
Disclosure

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.

Read SEC document
May 07, 2025 Filed May 9, 2025 20:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2022 LTIP - PSUs · Derivative 22,796 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-012467 · form4-05092025_040501.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 22,796 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 PSU represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F5 · derivative.exercise_date: On January 1, 2022, the Reporting Person was awarded 22,796 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2022 through December 31, 2024. 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 January 1, 2025 and settled upon certification by the Compensation Committee.

F5 · derivative.expiration_date: On January 1, 2022, the Reporting Person was awarded 22,796 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2022 through December 31, 2024. 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 January 1, 2025 and settled upon certification by the Compensation Committee.

Read SEC document
May 07, 2025 Filed May 9, 2025 20:05 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 33,282 Not disclosed Not disclosed
Disclosure

SEC source: 0001415889-25-012467 · form4-05092025_040501.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 115,326

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 Performance Stock Unit ("PSU") settles for one share of the Issuer's Common Stock.

Read SEC document
March 06, 2025 Filed Mar 10, 2025 20:28 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2023 IPO RSU Grant (3-Year) · Derivative 50,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001415889-25-007520 · form4-03102025_080353.xml · derivative · entry 3

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

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 · security: On January 12, 2023, in conjunction with the Company's IPO the Reporting Person was granted an RSU award in the amount of 100,000 RSUs; 50,000 of the RSUs vested on January 12, 2025 and settled on March 6, 2025. The remaining 50,000 RSUs will fully vest on January 12, 2026 subject to the Reporting Person's continuous service through the vesting date.

F1 · derivative.exercise_price: Each Restricted Stock Unit ("RSU") represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F1 · price: Each Restricted Stock Unit ("RSU") represents the right to receive, at settlement, one share of Common Stock of the Issuer.

F4 · derivative.exercise_date: On January 12, 2023, in conjunction with the Company's IPO the Reporting Person was granted an RSU award in the amount of 100,000 RSUs; 50,000 of the RSUs vested on January 12, 2025 and settled on March 6, 2025. The remaining 50,000 RSUs will fully vest on January 12, 2026 subject to the Reporting Person's continuous service through the vesting date.

F4 · derivative.expiration_date: On January 12, 2023, in conjunction with the Company's IPO the Reporting Person was granted an RSU award in the amount of 100,000 RSUs; 50,000 of the RSUs vested on January 12, 2025 and settled on March 6, 2025. The remaining 50,000 RSUs will fully vest on January 12, 2026 subject to the Reporting Person's continuous service through the vesting date.

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March 06, 2025 Filed Mar 10, 2025 20:28 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 20,311 $50.24 $1,020,422.61
Disclosure

SEC source: 0001415889-25-007520 · form4-03102025_080353.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 82,044

F2 · kind: 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.

F3 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $49.53- $51.47, inclusive (weighted average of $50.2399). 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.

Read SEC document
March 06, 2025 Filed Mar 10, 2025 20:28 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 50,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001415889-25-007520 · form4-03102025_080353.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,355

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") represents the right to receive, at settlement, one share of Common Stock of the Issuer.

Read SEC document
February 25, 2025 Filed Feb 27, 2025 22:34 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2025 LTIP - PSUs · Derivative 10,133 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-005875 · form4-02272025_100243.xml · derivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,133

Underlying: Common Stock · 10,133 shares

Expires not disclosed

F4 · derivative.exercise_price: On February 25, 2025, the Reporting Person was granted 10,133 PSUs. Each PSU is equivalent to one share of the Company's Common Stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2027.

F4 · derivative.exercise_date: On February 25, 2025, the Reporting Person was granted 10,133 PSUs. Each PSU is equivalent to one share of the Company's Common Stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2027.

F4 · derivative.expiration_date: On February 25, 2025, the Reporting Person was granted 10,133 PSUs. Each PSU is equivalent to one share of the Company's Common Stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2027.

Read SEC document
February 25, 2025 Filed Feb 27, 2025 22:34 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2025 LTIP - PSUs · Derivative 10,133 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-005875 · form4-02272025_100243.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,133

Underlying: Common Stock · 10,133 shares

Expires not disclosed

F3 · derivative.exercise_price: On February 25, 2025, the Reporting Person was granted 10,133 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's Common Stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2027.

F3 · derivative.exercise_date: On February 25, 2025, the Reporting Person was granted 10,133 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's Common Stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2027.

F3 · derivative.expiration_date: On February 25, 2025, the Reporting Person was granted 10,133 Performance Share Units ("PSUs"). Each PSU is equivalent to one share of the Company's Common Stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2027.

Read SEC document
February 25, 2025 Filed Feb 27, 2025 22:34 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Grant2025 LTIP - RSUs · Derivative 10,133 $0.00 $0.00
Disclosure

SEC source: 0001415889-25-005875 · form4-02272025_100243.xml · derivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,133

Underlying: Common Stock · 10,133 shares

Expires not disclosed

F1 · derivative.exercise_price: Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of the Company's Common Stock.

F2 · derivative.exercise_date: Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2028.

F2 · derivative.expiration_date: Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2028.

Read SEC document
January 08, 2025 Filed Jan 10, 2025 21:10 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 262 $45.53 $11,928.07
Disclosure

SEC source: 0001415889-25-001248 · form4-01102025_040101.xml · nonDerivative · entry 5

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 52,355

F4 · kind: On January 1, 2022, the Reporting Person was granted a Restricted Stock Award in the amount of 22,796 shares. Each share is equivalent to one share of the Company's common stock. This award fully vested on January 1, 2025. Sales transacted to cover taxes and fees incurred by vesting event.

F5 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 8, 2024.

Read SEC document
January 07, 2025 Filed Jan 10, 2025 21:10 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 1,294 $45.51 $58,888.90
Disclosure

SEC source: 0001415889-25-001248 · form4-01102025_040101.xml · nonDerivative · entry 4

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 52,617

F4 · kind: On January 1, 2022, the Reporting Person was granted a Restricted Stock Award in the amount of 22,796 shares. Each share is equivalent to one share of the Company's common stock. This award fully vested on January 1, 2025. Sales transacted to cover taxes and fees incurred by vesting event.

F5 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 8, 2024.

F7 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $45.3801-$45.76, inclusive (weighted average of $45.5092). 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.

Read SEC document
January 07, 2025 Filed Jan 10, 2025 21:10 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 1,414 $45.13 $63,817.92
Disclosure

SEC source: 0001415889-25-001248 · form4-01102025_040101.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 53,911

F4 · kind: On January 1, 2022, the Reporting Person was granted a Restricted Stock Award in the amount of 22,796 shares. Each share is equivalent to one share of the Company's common stock. This award fully vested on January 1, 2025. Sales transacted to cover taxes and fees incurred by vesting event.

F5 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 8, 2024.

F6 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $44.3818-$45.38, inclusive (weighted average of $45.1329). 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.

Read SEC document
January 07, 2025 Filed Jan 10, 2025 21:10 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 4,538 $45.47 $206,342.41
Disclosure

SEC source: 0001415889-25-001248 · form4-01102025_040101.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 55,325

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

F3 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $45.3268-$45.7371, inclusive (weighted average of $45.4699). 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.

Read SEC document
January 07, 2025 Filed Jan 10, 2025 21:10 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 3,766 $45.07 $169,716.30
Disclosure

SEC source: 0001415889-25-001248 · form4-01102025_040101.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 59,863

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

F2 · price: Prices reported in Column 4 are weighted average prices. Shares were sold in multiple transactions at prices ranging from $44.3283-$45.3186, inclusive (weighted average of $45.0654). 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.

Read SEC document
January 06, 2025 Filed Jan 7, 2025 00:43 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 47 $47.10 $2,213.70
Disclosure

SEC source: 0001415889-25-000935 · form4-01072025_120146.xml · nonDerivative · entry 5

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 63,629

F3 · kind: On January 1, 2022, the Reporting Person was granted a Restricted Stock Award in the amount of 22,796 shares. Each share is equivalent to one share of the Company's common stock. This award fully vested on January 1, 2025. Sales transacted to cover taxes and fees incurred by vesting event.

F4 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 8, 2024.

Read SEC document
January 06, 2025 Filed Jan 7, 2025 00:43 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 130 $47.11 $6,124.17
Disclosure

SEC source: 0001415889-25-000935 · form4-01072025_120146.xml · nonDerivative · entry 4

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 63,676

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

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $46.41 to $50.63, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
January 03, 2025 Filed Jan 7, 2025 00:43 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 3,695 $47.63 $175,974.38
Disclosure

SEC source: 0001415889-25-000935 · form4-01072025_120146.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 63,806

F3 · kind: On January 1, 2022, the Reporting Person was granted a Restricted Stock Award in the amount of 22,796 shares. Each share is equivalent to one share of the Company's common stock. This award fully vested on January 1, 2025. Sales transacted to cover taxes and fees incurred by vesting event.

F4 · shares: Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on August 8, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $46.41 to $50.63, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
January 03, 2025 Filed Jan 7, 2025 00:43 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 9,643 $47.83 $461,205.40
Disclosure

SEC source: 0001415889-25-000935 · form4-01072025_120146.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 67,501

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

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $46.41 to $50.63, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
January 02, 2025 Filed Jan 7, 2025 00:43 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 6,010 $49.37 $296,713.70
Disclosure

SEC source: 0001415889-25-000935 · form4-01072025_120146.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 77,144

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

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $46.41 to $50.63, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
May 10, 2024 Filed May 13, 2024 20:38 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 23,533 $37.21 $875,662.93
Disclosure

SEC source: 0001415889-24-012999 · form4-05132024_080524.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 83,154

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

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $37.17 to $37.27, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
May 09, 2024 Filed May 13, 2024 20:38 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversion2021 LTIP - Performance Share Units · Derivative 59,804 $0.00 $0.00
Disclosure

SEC source: 0001415889-24-012999 · form4-05132024_080524.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 59,804 shares

Expires not disclosed

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

F1 · derivative.exercise_price: Upon vesting, each Performance Stock Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.exercise_date: Upon vesting, each Performance Stock Unit ("PSU") settles for one share of the Company's common stock.

F1 · derivative.expiration_date: Upon vesting, each Performance Stock Unit ("PSU") settles for one share of the Company's common stock.

Read SEC document
May 09, 2024 Filed May 13, 2024 20:38 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 Exercise / conversionCommon Stock 59,804 Not disclosed Not disclosed
Disclosure

SEC source: 0001415889-24-012999 · form4-05132024_080524.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 106,687

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: Upon vesting, each Performance Stock Unit ("PSU") settles for one share of the Company's common stock.

Read SEC document
March 12, 2024 Filed Mar 13, 2024 20:08 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 14,243 $35.93 $511,750.99
Disclosure

SEC source: 0001415889-24-007793 · form4-03132024_080319.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 46,883

F1 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 30, 2023.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.38 to $36.13, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
March 11, 2024 Filed Mar 13, 2024 20:08 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 13,407 $35.63 $477,691.41
Disclosure

SEC source: 0001415889-24-007793 · form4-03132024_080319.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 61,126

F1 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 30, 2023.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.27 to $35.90, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
March 08, 2024 Filed Mar 8, 2024 22:13 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 12,109 $35.56 $430,596.04
Disclosure

SEC source: 0001415889-24-007390 · form4-03082024_100334.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 74,533

F1 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 30, 2023.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.2824 to $36.08, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
March 07, 2024 Filed Mar 8, 2024 22:13 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 10,241 $35.44 $362,941.04
Disclosure

SEC source: 0001415889-24-007390 · form4-03082024_100334.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 86,642

F1 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 30, 2023.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.17 to $35.73, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
March 06, 2024 Filed Mar 8, 2024 22:13 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 13,374 $35.70 $477,451.80
Disclosure

SEC source: 0001415889-24-007390 · form4-03082024_100334.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 96,883

F1 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 30, 2023.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.42 to $35.98, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

Read SEC document
March 05, 2024 Filed Mar 5, 2024 21:36 UTC Skyward Specialty Insurance Group, Inc. SKWD · Entity 4400 SaleCommon Stock 27,439 $35.32 $969,145.48
Disclosure

SEC source: 0001415889-24-006714 · form4-03052024_090321.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 110,257

F1 · shares: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 30, 2023.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.08 to $36.10, inclusive. The Reporting Person undertakes to provide the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth above.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.