Skyward Specialty Insurance Group (SKWD) CEO buys 22,100 shares

Rhea-AI Filing Summary

Skyward Specialty Insurance Group Chairman and CEO Andrew S. Robinson reported open-market purchases of a total of 22,100 shares of common stock. The transactions were executed at weighted average prices of $46.57 and $46.94 per share across multiple trades within stated price ranges.

Following these purchases, Robinson directly owns 167,674 shares of Skyward Specialty Insurance Group common stock. Both transactions are classified as open-market purchases and increase his direct ownership stake.

Insider Trade Summary

Net Buyer: 22,100 shares ($1,033,370)

Net Buy 2 txns

Insider Robinson Andrew S

Role Chairman & CEO, Skyward Group

Bought 22,100 shs ($1.03M)

Type	Security	Shares	Price	Value
Purchase	Common Stock	10,821	$46.57	$504K
Purchase	Common Stock	11,279	$46.94	$529K

Holdings After Transaction: Common Stock — 156,395 shares (Direct)

Footnotes (1)

1. Prices reported in Column 4 are weighted average prices. Shares were purchased in multiple transactions at prices ranging from $45.75-$46.74, inclusive (weighted average of $46.57). Reporting Person undertakes to provide to Issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth herein. Prices reported in Column 4 are weighted average prices. Shares were purchased in multiple transactions at prices ranging from $46.75-$47.32, inclusive (weighted average of $46.94). Reporting Person undertakes to provide to Issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth herein.

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^*

Robinson Andrew S

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chairman & CEO, Skyward Group

3. Date of Earliest Transaction (Month/Day/Year)
02/27/2026

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	02/27/2026		P		10,821	A	$46.57(1)	156,395	D
Common Stock	02/27/2026		P		11,279	A	$46.94(2)	167,674	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. Prices reported in Column 4 are weighted average prices. Shares were purchased in multiple transactions at prices ranging from $45.75-$46.74, inclusive (weighted average of $46.57). Reporting Person undertakes to provide to Issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth herein.

2. Prices reported in Column 4 are weighted average prices. Shares were purchased in multiple transactions at prices ranging from $46.75-$47.32, inclusive (weighted average of $46.94). Reporting Person undertakes to provide to Issuer or staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth herein.

	/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).
** 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 transactions did Andrew S. Robinson report for Skyward Specialty Insurance Group (SKWD)?

Andrew S. Robinson reported two open-market purchases totaling 22,100 shares of Skyward Specialty Insurance Group common stock. These buys increased his direct holdings and were executed at weighted average prices of $46.57 and $46.94 per share.

How many Skyward Specialty Insurance Group (SKWD) shares does Andrew S. Robinson now own?

After the reported purchases, Andrew S. Robinson directly owns 167,674 shares of Skyward Specialty Insurance Group common stock. This figure reflects his holdings immediately following the second open-market transaction disclosed in the filing data provided.

At what prices did the Skyward Specialty Insurance Group (SKWD) CEO buy shares?

Andrew S. Robinson bought Skyward Specialty Insurance Group common stock at weighted average prices of $46.57 and $46.94 per share. Each average reflects multiple trades executed within specified intraday price ranges noted in the footnotes.

Were Andrew S. Robinson’s Skyward Specialty Insurance Group (SKWD) share purchases direct or indirect?

The reported Skyward Specialty Insurance Group share purchases by Andrew S. Robinson are classified as direct ownership. The transactions are labeled with a direct ownership code, and no footnotes indicate that the shares are held through a separate entity or trust.

What type of transactions did Skyward Specialty Insurance Group (SKWD) report for its CEO?

Skyward Specialty Insurance Group reported open-market purchases of common stock by CEO Andrew S. Robinson. Both transactions are coded as purchases, indicating he increased his direct stake rather than selling or disposing of existing holdings.