Skyward Specialty director exercises 1,797 RSUs

Skyward Specialty Insurance Group director Anthony J. Kuczinski reported equity compensation activity.

Rhea-AI Filing Summary

Skyward Specialty Insurance Group director Anthony J. Kuczinski reported equity compensation activity. On May 7, 2026, he exercised 1,797 restricted stock units from a 2025 award, receiving the same number of common shares and bringing his direct common stock holdings to 13,977 shares.

On May 6, 2026, he was granted a new 2026 RSU Award covering 3,334 RSUs. Each RSU settles into one share of common stock, and this award is scheduled to fully vest on the date of the company’s 2027 Annual Meeting of Shareholders, subject to the award terms.

Insider Trade Summary

1,797 shares exercised/converted

Exercise 3 txns

Insider Kuczinski Anthony J

Role Director

Type	Security	Shares	Price	Value
Exercise	2025 RSU Award	1,797	$0.00	$0.00
Exercise	Common Stock	1,797	$0.00	$0.00
Grant/Award	2026 RSU Award	3,334	$0.00	$0.00

Holdings After Transaction: 2026 RSU Award — 3,334 contracts (Direct); 2025 RSU Award — 0 contracts (Direct); Common Stock — 13,977 shares (Direct)

Footnotes (4)

1. F1. Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.
2. F2. Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.
3. F3. On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.
4. F4. On May 7, 2025, the Reporting Person was granted an RSU Award in the amount of 1,797 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 7, 2026.

Key Figures

RSUs exercised: 1,797 RSUs Shares received from RSU settlement: 1,797 shares Shares held after transactions: 13,977 shares +3 more

6 metrics

RSUs exercised 1,797 RSUs 2025 RSU Award settled into common stock on May 7, 2026

Shares received from RSU settlement 1,797 shares Common stock received when 2025 RSUs vested and settled May 7, 2026

Shares held after transactions 13,977 shares Direct common stock ownership following May 7, 2026 settlement

2026 RSU Award size 3,334 RSUs New RSU grant dated May 6, 2026

2026 RSU vesting event 2027 Annual Meeting Award scheduled to fully vest on the 2027 Annual Meeting date

2025 RSU grant date May 7, 2025 Original grant date for 1,797 RSUs that vested May 7, 2026

Key Terms

Restricted Stock Unit ("RSU"), RSU Award, vest, Annual Meeting of Shareholders, +1 more

5 terms

Restricted Stock Unit ("RSU") financial

"Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock."

RSU Award financial

"On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs."

vest financial

"Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders."

A vest is the process by which an employee earns the right to receive certain benefits or ownership interests, such as stock or retirement funds, over time. It’s similar to earning a reward gradually, ensuring that the benefit becomes fully yours only after a set period or meeting specific conditions. This makes it important for investors because it determines when they can actually claim or use those benefits.

Annual Meeting of Shareholders financial

"this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders."

A yearly gathering where a company’s owners (shareholders) vote on key items like electing the board, approving executive pay, and ratifying auditors, and receive updates on performance and strategy. Think of it as an annual town hall for owners: it matters to investors because outcomes and disclosures can affect leadership, corporate direction, dividend and governance policies, and therefore the company’s risk and potential return.

grant financial

"On May 7, 2025, the Reporting Person was granted an RSU Award in the amount of 1,797 RSUs."

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transactions did Skyward Specialty (SKWD) director Anthony J. Kuczinski report?

He reported acquiring shares via restricted stock units. On May 7, 2026, 1,797 RSUs from a 2025 award settled into 1,797 common shares, and on May 6, 2026, he received a new grant of 3,334 RSUs.

How many Skyward Specialty (SKWD) shares does Anthony J. Kuczinski hold after these transactions?

After the May 7, 2026 settlement of RSUs, Anthony J. Kuczinski directly holds 13,977 shares of Skyward Specialty common stock. This figure reflects his reported post-transaction ownership in the filing’s non-derivative holdings table.

What are the terms of Anthony J. Kuczinski’s 2026 RSU Award at Skyward Specialty (SKWD)?

The 2026 RSU Award covers 3,334 restricted stock units. Each RSU settles into one share of common stock and, subject to the award agreement, the entire grant will fully vest on the date of Skyward Specialty’s 2027 Annual Meeting of Shareholders.

What happened to Anthony J. Kuczinski’s 2025 RSU Award at Skyward Specialty (SKWD)?

The 2025 RSU Award for 1,797 RSUs fully vested on May 7, 2026. On that date, the vested RSUs settled into 1,797 shares of Skyward Specialty common stock, and the derivative RSU position was reduced to zero in the filing.

How do RSUs reported by Skyward Specialty (SKWD) for Anthony J. Kuczinski convert into shares?

Each restricted stock unit, or RSU, reported for Anthony J. Kuczinski settles into one share of Skyward Specialty common stock after vesting and upon settlement, as described in the filing’s footnotes for the RSU awards.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 05/08/2026 - 04:26 PM Learn about SEC filing dates

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^*

Kuczinski Anthony J

(Last) (First) (Middle)

800 GESSNER ROAD

SUITE 600

(Street)

HOUSTON TEXAS 77024

(City) (State) (Zip)

UNITED STATES

(Country)

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
	Officer (give title below)		Other (specify below)

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/06/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	05/07/2026		M		1,797	A	(1)	13,977	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
2026 RSU Award	(2)	05/06/2026		A		3,334		(3)	(3)	Common Stock	3,334	$0	3,334	D
2025 RSU Award	(2)	05/07/2026		M			1,797	(4)	(4)	Common Stock	1,797	$0	0	D

Explanation of Responses:

1. Each Restricted Stock Unit ("RSU") settles for one share of the Issuer's Common Stock.

2. Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.

3. On May 6, 2026, the Reporting Person was granted an RSU Award in the amount of 3,334 RSUs. Subject to the terms of the award agreement, this award will fully vest on the date of the Issuer's 2027 Annual Meeting of Shareholders.

4. On May 7, 2025, the Reporting Person was granted an RSU Award in the amount of 1,797 RSUs. Subject to the terms of the RSU Agreement, this award fully vested on May 7, 2026.

	/s/ Stacy E. Skelton, Attorney-in-Fact	05/08/2026
	** 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).
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.
* Form 4: SEC 1474 (03-26)