Skyward Specialty Insurance Group (SKWD) officer reports Rule 10b5-1 sales

Rhea-AI Filing Summary

Skyward Specialty Insurance Group, Inc. reported insider stock sales by its Head of Actuarial, an officer of the company, on 12/12/2025. The officer sold 1,486 shares of common stock at $50.03 per share and 1,200 shares at $50.01 per share, leaving 14,289 and then 13,089 shares beneficially owned directly after the respective transactions.

The sales were effected under a Rule 10b5-1 trading plan adopted on September 8, 2025. The reported share balance also reflects the acquisition of 231 shares on June 1, 2025 and 197 shares on December 1, 2025 through the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan "ESPP" for purchase periods from December 1, 2024 to May 31, 2025 and from June 1, 2025 to November 30, 2025.

Insider Trade Summary

Net Seller: 2,686 shares ($134,357)

Net Sell 2 txns

Insider Kapadia Sandip A

Role Head of Actuarial

Sold 2,686 shs ($134K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,486	$50.03	$74K
Sale	Common Stock	1,200	$50.01	$60K

Holdings After Transaction: Common Stock — 14,289 shares (Direct)

Footnotes (1)

1. Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 8, 2025. The number of securities reported reflects the June 1, 2025 acquisition of 231 shares and the December 1, 2025 acquisition of 197 shares of the Company's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively.

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).

X

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)
12/12/2025

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	12/12/2025		S		1,486(1)	D	$50.03	14,289(2)	D
Common Stock	12/12/2025		S		1,200(1)	D	$50.01	13,089	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

Explanation of Responses:

1. Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 8, 2025.

2. The number of securities reported reflects the June 1, 2025 acquisition of 231 shares and the December 1, 2025 acquisition of 197 shares of the Company's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively.

	/s/ Stacy E. Skelton, Attorney-in-Fact	12/16/2025
	** 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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What insider transaction did Skyward Specialty Insurance Group (SKWD) report?

An officer of Skyward Specialty Insurance Group, Inc., serving as Head of Actuarial, reported selling shares of the company's common stock in two transactions on 12/12/2025.

How many SKWD shares were sold and at what prices?

The officer sold 1,486 shares of common stock at $50.03 per share and 1,200 shares at $50.01 per share, all on 12/12/2025.

What is the reporting person's role at Skyward Specialty Insurance Group (SKWD)?

The reporting person is an officer of Skyward Specialty Insurance Group, Inc., with the title Head of Actuarial.

Were the SKWD stock sales made under a Rule 10b5-1 trading plan?

Yes. The sales were effected pursuant to a Rule 10b5-1 trading plan that the reporting person adopted on September 8, 2025.

How many Skyward Specialty (SKWD) shares did the officer own after these transactions?

After the first sale, the officer beneficially owned 14,289 shares directly, and after the second sale, the officer beneficially owned 13,089 shares directly.

What employee stock purchase activity is included in the reported SKWD share balance?

The reported holdings include shares acquired through the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan, specifically 231 shares acquired on June 1, 2025 and 197 shares acquired on December 1, 2025 for two ESPP purchase periods.