RSU vesting boosts Skyward (NASDAQ: SKWD) CPO Schmitt holdings shares

Rhea-AI Filing Summary

Skyward Specialty Insurance Group CPO Thomas N. Schmitt reported stock activity tied to previously granted restricted stock units. On January 12, 2026, 5,000 shares of common stock were issued upon settlement of a 2023 IPO 4-year RSU grant and another 5,000 shares were issued from a 2023 IPO 3-year RSU grant, both at an exercise price of $0. To satisfy tax withholding on these vestings, the issuer withheld 2,149 shares and 1,968 shares at a price of $46.10 per share, which the footnotes state was mandated by the company and not a discretionary sale by Schmitt. Following these transactions, Schmitt directly beneficially owned 17,363 shares of Skyward common stock, and 5,000 RSUs from the 4-year grant remain outstanding.

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

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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^*

Schmitt Thomas N

(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)
	CPO, Skyward Group

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	16,480	D
Common Stock	01/12/2026		F(2)		2,149	D	$46.1(3)	14,331	D
Common Stock	01/12/2026		M		5,000(1)	A	$0	19,331	D
Common Stock	01/12/2026		F(2)		1,968	D	$46.1(3)	17,363	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.
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FAQ

What insider activity did Skyward Specialty (SKWD) report for Thomas N. Schmitt?

The filing shows CPO Thomas N. Schmitt settled RSU awards into common stock on January 12, 2026, receiving 10,000 shares from two 2023 IPO RSU grants and having shares withheld to cover taxes.

How many Skyward Specialty (SKWD) shares does Thomas Schmitt hold after the Form 4 transactions?

After the reported transactions on January 12, 2026, Thomas N. Schmitt beneficially owned 17,363 shares of Skyward Specialty Insurance Group common stock directly.

Were the Skyward (SKWD) share dispositions by Thomas Schmitt discretionary sales?

No. The footnotes state that the dispositions of 2,149 and 1,968 shares were shares withheld by the issuer to cover tax withholding obligations upon RSU vesting and were mandated by the issuer, not discretionary transactions.

What RSU grants are described in the Skyward Specialty (SKWD) Form 4?

The filing describes two 2023 IPO RSU awards of 10,000 RSUs each granted on January 12, 2023: a 4-year grant where 50% vested on January 12, 2026, with the remaining 50% scheduled to vest on January 12, 2027, and a 3-year grant where 50% vested on January 12, 2025 and the remaining 50% vested on January 12, 2026.

At what price were Skyward Specialty (SKWD) shares withheld for Thomas Schmitts taxes?

The number of shares withheld for Thomas Schmitts tax obligations was calculated using the $46.10 closing price of Skywards common stock on the vesting date of January 12, 2026, as stated in the footnotes.

How many Skyward (SKWD) RSUs remain outstanding for Thomas Schmitt after this Form 4?

Table II shows that after settlement on January 12, 2026, 5,000 RSUs remain beneficially owned from the 2023 IPO 4-year RSU grant, while the 2023 IPO 3-year RSU grant is fully settled with 0 RSUs remaining.