Skyward Specialty (SKWD) EVP Duffy reports RSU vesting, tax shares

Rhea-AI Filing Summary

Skyward Specialty Insurance Group EVP & Chief Claims Officer Sean W. Duffy reported restricted stock unit vesting and related tax withholding transactions in company stock. On January 12, 2026, 5,000 shares of common stock were issued upon settlement of a 2023 IPO RSU grant and another 5,000 shares were issued from a separate 2023 IPO RSU grant, both at an exercise price of $0. To cover tax obligations tied to these RSU vestings, the issuer withheld 2,276 shares and 2,095 shares at a price of $46.10 per share, which the filing notes as mandated by the company rather than discretionary sales by Duffy. Following these transactions, Duffy directly beneficially owned 16,036 shares of Skyward Specialty Insurance Group common stock.

Insider Trade Summary

10,000 shares exercised/converted

Mixed 6 txns

Insider Duffy Sean W

Role EVP & Chief Claims Officer

Type	Security	Shares	Price	Value
Exercise	2023 IPO RSU Grant (4-Year)	5,000	$0.00	--
Exercise	2023 IPO RSU Grant (3-Year)	5,000	$0.00	--
Exercise	Common Stock	5,000	$0.00	--
Tax Withholding	Common Stock	2,276	$46.10	$105K
Exercise	Common Stock	5,000	$0.00	--
Tax Withholding	Common Stock	2,095	$46.10	$97K

Holdings After Transaction: 2023 IPO RSU Grant (4-Year) — 5,000 shares (Direct); 2023 IPO RSU Grant (3-Year) — 0 shares (Direct); Common Stock — 15,407 shares (Direct)

Footnotes (1)

1. 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. 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. 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. Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement. On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027. On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.

Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Duffy Sean W

(Last) (First) (Middle)

800 GESSNER

SUITE 600

(Street)

HOUSTON TX 77024

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Skyward Specialty Insurance Group, Inc. [ SKWD ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	EVP & Chief Claims Officer

3. Date of Earliest Transaction (Month/Day/Year)
01/12/2026

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	01/12/2026		M		5,000(1)	A	$0	15,407	D
Common Stock	01/12/2026		F(2)		2,276	D	$46.1(3)	13,131	D
Common Stock	01/12/2026		M		5,000(1)	A	$0	18,131	D
Common Stock	01/12/2026		F(2)		2,095	D	$46.1(3)	16,036	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
2023 IPO RSU Grant (4-Year)	(4)	01/12/2026		M			5,000	(5)	(5)	Common Stock	5,000	$0	5,000	D
2023 IPO RSU Grant (3-Year)	(4)	01/12/2026		M			5,000	(6)	(6)	Common Stock	5,000	$0	0	D

Explanation of Responses:

1. 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.

2. 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.

3. 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.

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

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

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

	/s/ Stacy E. Skelton, Attorney-in-Fact	01/14/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
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FAQ

What insider activity did SKWD EVP Sean W. Duffy report on this Form 4?

EVP & Chief Claims Officer Sean W. Duffy reported the vesting and settlement of two 2023 IPO RSU grants into common stock on January 12, 2026, along with issuer-mandated share withholding to cover related tax obligations.

How many Skyward Specialty (SKWD) shares were issued from RSU settlements?

On January 12, 2026, a total of 10,000 shares of Skyward Specialty Insurance Group, Inc. common stock were issued to Sean W. Duffy upon settlement of two 2023 IPO RSU awards, with 5,000 shares from each grant.

How many SKWD shares were withheld for taxes in this insider filing?

The company withheld 2,276 shares and 2,095 shares of common stock, calculated using a share price of $46.10 on January 12, 2026, to satisfy tax withholding obligations tied to the RSU vesting.

Were the SKWD share dispositions by Sean W. Duffy discretionary sales?

No. The filing explains that the reported dispositions represent shares withheld by the issuer to cover tax obligations upon RSU vesting and that this withholding is mandated by the issuer, not a discretionary transaction by Duffy.

How many Skyward Specialty (SKWD) shares does Sean W. Duffy own after these transactions?

After the reported RSU settlements and tax share withholding on January 12, 2026, Sean W. Duffy directly beneficially owned 16,036 shares of Skyward Specialty Insurance Group, Inc. common stock.

What do the Form 4 footnotes say about Sean W. Duffy’s 2023 RSU awards?

Footnotes state each RSU represents the right to receive one share upon settlement and that Duffy received two 2023 RSU awards of 10,000 RSUs each. For one award, 50% vested on January 12, 2026 with the remaining 50% scheduled to vest on January 12, 2027, while the other award vested 50% on January 12, 2025 and the remaining 50% on January 12, 2026.