Director buys 2,000 Skyward Specialty (SKWD) shares in open market

Rhea-AI Filing Summary

Skyward Specialty Insurance Group, Inc. director Anthony J. Kuczinski reported open-market purchases of a total of 2,000 shares of common stock on May 21, 2026, at prices of $47.00 and $47.20 per share, bringing his direct holdings to 15,977 shares.

Insider Trade Summary

Net Buyer: 2,000 shares ($94,200)

Net Buy 3 txns

Insider Kuczinski Anthony J

Role null

Bought 2,000 shs ($94K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	200	$47.00	$9K
Purchase	Common Stock	800	$47.00	$38K
Purchase	Common Stock	1,000	$47.20	$47K

Holdings After Transaction: Common Stock — 14,177 shares (Direct, null)

Footnotes (1)

Key Figures

Shares purchased (largest trade): 1,000 shares Additional shares purchased: 800 shares Additional shares purchased: 200 shares +4 more

7 metrics

Shares purchased (largest trade) 1,000 shares Common Stock bought at $47.20 on May 21, 2026

Additional shares purchased 800 shares Common Stock bought at $47.00 on May 21, 2026

Additional shares purchased 200 shares Common Stock bought at $47.00 on May 21, 2026

Total shares purchased 2,000 shares Sum of three open-market purchases on May 21, 2026

Price per share (largest trade) $47.20/share Open-market purchase of 1,000 Common Stock shares

Other trade price $47.00/share Open-market purchases of 800 and 200 Common Stock shares

Holdings after transactions 15,977 shares Total direct Common Stock owned after May 21, 2026

Key Terms

open-market purchase, Common Stock, non-derivative, transaction code "P"

4 terms

open-market purchase financial

"transaction_action: "open-market purchase" for each Common Stock trade"

An open-market purchase is when an investor or a company buys shares on a public stock exchange at the going market price, rather than through a private deal. It matters to investors because these purchases change how many shares are available, can push the stock price up or signal confidence from large buyers, and often affect per-share metrics like earnings—think of it like someone buying lots of apples off a grocery shelf, reducing supply and potentially raising the price.

Common Stock financial

"security_title: "Common Stock" in all three transactions"

Common stock represents ownership shares in a company, giving investors a stake in its success and a say in important decisions through voting rights. It is the most common type of stock traded on markets and can provide income through dividends, as well as potential for value growth. For investors, holding common stock means sharing in the company’s profits and risks.

non-derivative financial

"transaction_type: "non-derivative" for each reported transaction"

transaction code "P" financial

"transaction_code: "P" described as "Purchase in open market or private transaction""

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^*

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)
05/21/2026

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	05/21/2026		P		200	A	$47	14,177	D
Common Stock	05/21/2026		P		800	A	$47	14,977	D
Common Stock	05/21/2026		P		1,000	A	$47.2	15,977	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

Explanation of Responses:

	/s/ Stacy E. Skelton, Attorney-in-Fact	05/21/2026
	** 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)

FAQ

What insider activity did Skyward Specialty Insurance Group (SKWD) report in this Form 4?

Skyward Specialty director Anthony J. Kuczinski reported buying 2,000 shares of common stock in open-market transactions. These trades occurred on May 21, 2026, and increased his direct ownership stake in the company to 15,977 shares following the reported purchases.

How many Skyward Specialty (SKWD) shares did Anthony J. Kuczinski purchase?

Anthony J. Kuczinski purchased a total of 2,000 Skyward Specialty common shares. The Form 4 lists three separate open-market trades: 1,000 shares, 800 shares, and 200 shares, all executed on May 21, 2026, at prices around the mid-$40s per share.

At what prices did the Skyward Specialty (SKWD) director buy shares?

The director’s purchases were made at per-share prices of $47.00 and $47.20. One transaction covered 1,000 shares at $47.20, while two additional trades of 800 and 200 shares were executed at $47.00 on the same trading date, May 21, 2026.

What is Anthony J. Kuczinski’s Skyward Specialty (SKWD) ownership after these trades?

After the reported purchases, Anthony J. Kuczinski directly owns 15,977 shares of Skyward Specialty common stock. This post-transaction holding figure is taken directly from the Form 4 and reflects his position immediately following the May 21, 2026 transactions.

Were the Skyward Specialty (SKWD) insider transactions buys or sales?

All reported transactions were open-market purchases of common stock. The Form 4 uses transaction code “P” and notes the direction as “buy,” with no sales, gifts, tax withholdings, or derivative exercises disclosed in this particular filing.

Did the Skyward Specialty (SKWD) Form 4 include any derivative securities?

No derivative securities were reported in this Form 4. All three transactions involved non-derivative common stock, and the derivative summary section is empty, indicating no option exercises, conversions, or other derivative-related activity in this filing.