Skyward Specialty (NASDAQ: SKWD) CEO reports RSU vesting, tax withholding

Rhea-AI Filing Summary

Skyward Specialty Insurance Group Chairman and CEO Andrew S. Robinson reported the vesting and settlement of restricted stock units into common stock. On January 12, 2026, 100,000 RSUs from two 2023 IPO grants converted into 100,000 shares of common stock at an exercise price of $0. In connection with this vesting, a total of 39,532 shares were withheld by the company to cover tax obligations, using a share value of $46.10 on the vesting date. After these transactions, Robinson directly beneficially owned 134,915 shares of common stock. The 4-year IPO RSU grant shows 50,000 derivative RSUs remaining outstanding, while the 3-year IPO RSU grant is now fully settled.

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^*

Robinson Andrew S

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chairman & CEO, 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		50,000(1)	A	$0	124,447	D
Common Stock	01/12/2026		F(2)		19,857	D	$46.1(3)	104,590	D
Common Stock	01/12/2026		M		50,000(1)	A	$0	154,590	D
Common Stock	01/12/2026		F(2)		19,675	D	$46.1(3)	134,915	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			50,000	(5)	(5)	Common Stock	50,000	$0	50,000	D
2023 IPO RSU Grant (3-Year)	(4)	01/12/2026		M			50,000	(6)	(6)	Common Stock	50,000	$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 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.

6. 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.

	/s/ Stacy E. Skelton, Attorney-in-Fact	01/14/2026
	** Signature of Reporting Person	Date
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FAQ

What does the Skyward Specialty (SKWD) Form 4 filing report for Andrew Robinson?

The filing reports that Chairman and CEO Andrew S. Robinson settled vested restricted stock units into common stock and had a portion of the resulting shares withheld to cover tax obligations.

How many Skyward Specialty RSUs vested and settled for Andrew Robinson?

On January 12, 2026, a total of 100,000 RSUs from two 2023 IPO grants vested and settled into 100,000 shares of Skyward Specialty common stock.

How many Skyward Specialty (SKWD) shares were withheld for taxes and at what price?

The company withheld 39,532 shares of common stock to satisfy tax withholding obligations, using the closing price of $46.10 per share on January 12, 2026.

How many Skyward Specialty shares does Andrew Robinson own after these Form 4 transactions?

Following the reported transactions, Andrew Robinson directly beneficially owned 134,915 shares of Skyward Specialty common stock.

What RSU grants are disclosed in this Skyward Specialty Form 4?

The Form 4 discloses two 2023 IPO RSU grants of 100,000 RSUs each, one with a 4-year schedule and one with a 3-year schedule, with all RSUs now vested on the 3-year grant and 50,000 RSUs remaining from the 4-year grant.

Was the share disposition in the Skyward Specialty (SKWD) Form 4 discretionary?

No. The disposition of shares was mandated by the issuer to cover tax withholding obligations and is described as not a discretionary transaction by Andrew Robinson.