Skyward Specialty (SKWD) actuarial head gains stock awards, shares withheld for taxes

Rhea-AI Filing Summary

Skyward Specialty Insurance Group, Inc. Head of Actuarial Sandip A. Kapadia reported multiple equity compensation moves. He acquired common shares through the settlement of performance share units and received new grants of restricted stock units and additional performance share units under long-term incentive plans.

The new awards include 2,884 RSUs vesting on January 1, 2029, 2,884 PSUs that can vest between 0% and 200% of target and fully vest on December 31, 2028, and 4,326 RSUs vesting 50% on January 1, 2029 and 50% on January 1, 2030. Separately, 847 common shares were withheld at $45.89 per share to cover tax obligations, a disposition mandated by the company rather than a discretionary sale, leaving him with 17,041 common shares held directly.

Insider Trade Summary

2,020 shares exercised/converted

Mixed 6 txns

Insider Kapadia Sandip A

Role Head of Actuarial

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock	847	$45.89	$39K
Exercise	2023 LTIP - PSUs	2,020	$0.00	--
Grant/Award	2026 LTIP - RSUs	2,884	$0.00	--
Grant/Award	2026 LTIP - PSUs	2,884	$0.00	--
Grant/Award	2026 Bright Future - RSUs	4,326	$0.00	--
Exercise	Common Stock	2,343	$0.00	--

Holdings After Transaction: Common Stock — 17,041 shares (Direct); 2023 LTIP - PSUs — 0 shares (Direct); 2026 LTIP - RSUs — 2,884 shares (Direct); 2026 LTIP - PSUs — 2,884 shares (Direct); 2026 Bright Future - RSUs — 4,326 shares (Direct)

Footnotes (1)

1. Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of 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 PSUs listed in Line I of Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person. Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement. On February 27, 2023, the Reporting Person was awarded 2,020 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 2,884 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029. On February 25, 2026, the Reporting Person was granted 2,884 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 4,326 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.

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

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

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)
02/25/2026

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	02/25/2026		M		2,343(1)	A	$0	17,888	D
Common Stock	02/26/2026		F(2)		847	D	$45.89	17,041	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 LTIP - PSUs	(3)	02/25/2026		M			2,020	(4)	(4)	Common Stock	2,020	$0	0	D
2026 LTIP - RSUs	(5)	02/25/2026		A		2,884		(6)	(6)	Common Stock	2,884	$0	2,884	D
2026 LTIP - PSUs	(7)	02/25/2026		A		2,884		(7)	(7)	Common Stock	2,884	$0	2,884	D
2026 Bright Future - RSUs	(5)	02/25/2026		A		4,326		(8)	(8)	Common Stock	4,326	$0	4,326	D

Explanation of Responses:

1. Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of 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 PSUs listed in Line I of Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

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

4. On February 27, 2023, the Reporting Person was awarded 2,020 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.

5. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.

6. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 2,884 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029.

7. On February 25, 2026, the Reporting Person was granted 2,884 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.

8. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 4,326 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.

	/s/ Stacy E. Skelton, Attorney-in-Fact	02/27/2026
	** 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).
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FAQ

What insider transactions did SKWD executive Sandip Kapadia report on this Form 4?

Sandip Kapadia reported equity compensation activity, including the settlement of performance share units into common stock and several new restricted stock unit and performance share unit grants. He also reported shares withheld to satisfy tax obligations related to the vesting and settlement of performance-based awards.

How many SKWD shares were withheld for taxes in Sandip Kapadia’s Form 4 filing?

The filing shows 847 shares of Skyward Specialty common stock were withheld at $45.89 per share to cover tax withholding obligations. Footnotes state this disposition was mandated by the issuer and did not represent a discretionary transaction or open-market sale by Sandip Kapadia.

What new RSU awards did Sandip Kapadia receive from Skyward Specialty (SKWD)?

Sandip Kapadia received 2,884 RSUs under the 2026 LTIP that vest 100% on January 1, 2029, subject to continued service, and 4,326 RSUs under the 2026 Bright Future program vesting 50% on January 1, 2029 and 50% on January 1, 2030.

What new PSU awards were granted to Sandip Kapadia in the SKWD Form 4?

The filing reports a grant of 2,884 performance share units on February 25, 2026. Each PSU equals one share of common stock, with vesting ranging from 0% to 200% of the target amount based on performance targets, and full vesting scheduled for December 31, 2028.

How many SKWD common shares does Sandip Kapadia hold after these transactions?

After the reported equity transactions and tax withholding, Sandip Kapadia directly holds 17,041 shares of Skyward Specialty common stock. This figure reflects the net position following PSU settlement into shares and the mandated share withholding to satisfy related tax obligations.

Were the tax-related SKWD share dispositions discretionary for Sandip Kapadia?

No. Footnotes explain the 847-share disposition was due to shares withheld to cover tax obligations related to PSU vesting and settlement. The company mandated this withholding, so it is not considered a discretionary transaction or open-market sale by Sandip Kapadia.