Skyward Specialty Insurance Group (SKWD) officer RSU vesting and tax share withholding detailed

Rhea-AI Filing Summary

Skyward Specialty Insurance Group Head of Actuarial Sandip A. Kapadia reported equity award activity tied to 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, with each RSU converting into one share of common stock at an exercise price of $0.

On the same date, the issuer withheld 1,985 shares and 1,808 shares of common stock, respectively, to satisfy tax withholding obligations, using a share value of $46.10 based on the closing price on the vesting date. After these transactions, Kapadia directly beneficially owned 15,545 shares of Skyward Specialty Insurance Group common stock. The filing states that the tax-related share withholding was mandated by the company and was not a discretionary sale.

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^*

Kapadia Sandip A

(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)
	Head of Actuarial

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	14,338	D
Common Stock	01/12/2026		F(2)		1,985	D	$46.1(3)	12,353	D
Common Stock	01/12/2026		M		5,000(1)	A	$0	17,353	D
Common Stock	01/12/2026		F(2)		1,808	D	$46.1(3)	15,545	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 transaction did SKWD report for Sandip Kapadia on January 12, 2026?

On January 12, 2026, Sandip A. Kapadia, Head of Actuarial at Skyward Specialty Insurance Group, reported the settlement of RSU awards that resulted in the issuance of 10,000 shares of common stock and related share withholding for taxes.

How many Skyward Specialty (SKWD) shares does Sandip Kapadia own after this Form 4?

Following the reported transactions, Sandip A. Kapadia beneficially owned 15,545 shares of Skyward Specialty Insurance Group common stock directly.

Were the SKWD shares withheld for Sandip Kapadia a discretionary sale?

No. The filing states the disposition represents shares withheld to cover tax withholding obligations in connection with RSU vesting and that this withholding is mandated by the issuer, not a discretionary transaction by Sandip Kapadia.

What RSU grants for SKWD vested for Sandip Kapadia on January 12, 2026?

The filing shows two awards: a 2023 IPO RSU Grant (4-Year) and a 2023 IPO RSU Grant (3-Year), each for 5,000 RSUs settling into 5,000 shares of common stock on January 12, 2026.

At what price were SKWD shares valued for tax withholding on Kapadia’s RSUs?

The number of shares withheld for tax obligations was calculated using the closing price of $46.10 for Skyward Specialty Insurance Group common stock on the vesting date, January 12, 2026.

Does each RSU in Kapadia’s SKWD awards equal one share of common stock?

Yes. The filing explains that each RSU represents the right to receive one share of Skyward Specialty Insurance Group common stock upon settlement.

What were the original sizes and vesting schedules of Kapadia’s 2023 SKWD RSU grants?

Each 2023 IPO RSU award was for 10,000 RSUs. For the 4-year grant, 50% vested on January 12, 2026, with the remaining 50% scheduled to vest on January 12, 2027, subject to continued service. For the 3-year grant, 50% vested on January 12, 2025 and the remaining 50% on January 12, 2026.