Sean W. Duffy - 01 Jan 2026 Form 4 Insider Report for Skyward Specialty Insurance Group, Inc. (SKWD)

Role: EVP & CHIEF CLAIMS OFFICER
Signature: /s/ Stacy E. Skelton, Attorney-in-Fact
Issuer symbol: SKWD
Transactions as of: 01 Jan 2026
Net transactions value: -$64,756
Form type: 4
Filing time: 05 Jan 2026, 16:39:38 UTC
Previous filing: 18 Mar 2025
Next filing: 14 Jan 2026
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Duffy Sean W	EVP & CHIEF CLAIMS OFFICER	800 GESSNER, SUITE 600, HOUSTON	/s/ Stacy E. Skelton, Attorney-in-Fact	05 Jan 2026	0001936008

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	SKWD	Common Stock	Options Exercise	$0	+2,861	+32%	$0.000000	11,674	01 Jan 2026	Direct	F1
transaction	SKWD	Common Stock	Tax liability	$64,756	-1,267	-11%	$51.11	10,407	01 Jan 2026	Direct	F2, F3

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	SKWD	2023 LTIP - RSUs	Options Exercise	$0	-2,861	-100%	$0.000000	0	01 Jan 2026	Common Stock	2,861		Direct	F4, F5

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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	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	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.
F4	Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.
F5	On February 27, 2023, the Reporting Person was granted an RSU Award in the amount of 2,861 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on January 1, 2026.