Director granted 3,334 RSUs at Skyward Specialty

Terry Katharine reported acquisition or exercise transactions in this Form 4 filing.

Rhea-AI Filing Summary

Terry Katharine reported acquisition or exercise transactions in this Form 4 filing.

Skyward Specialty Insurance Group, Inc. director Terry Katharine reported a new equity award. On May 6, 2026, she received a grant of 3,334 restricted stock units (RSUs), each representing one share of common stock after vesting and settlement.

The award will fully vest on the date of the company’s 2027 Annual Meeting of Shareholders, subject to the award terms. Katharine has elected to defer settlement of this RSU award until her separation from the company under the Deferred Compensation Plan for Non-Employee Directors. Following the reported transactions, she directly holds 6,780 shares of common stock.

Insider Trade Summary

Grant/Award: 3,334 shares

Grant/Award 2 txns

Insider Terry Katharine

Role Director

Type	Security	Shares	Price	Value
Grant/Award	2026 RSU Award	3,334	$0.00	$0.00
holding	Common Stock	--	--	--

Holdings After Transaction: 2026 RSU Award — 3,334 contracts (Direct); Common Stock — 6,780 shares (Direct)

Footnotes (3)

1. F1. Each RSU represents the right to receive, after vesting and upon settlement, one share of Common Stock of the Issuer.
2. F2. 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.
3. F3. The Reporting Person has elected to defer the settlement of this RSU award until their separation from the Company, pursuant to the Issuer's Deferred Compensation Plan for Non-Employee Directors.

Key Figures

RSU grant size: 3,334 RSUs Common shares held: 6,780 shares RSU-to-share ratio: 1 share per RSU

3 metrics

RSU grant size 3,334 RSUs 2026 RSU Award granted on May 6, 2026

Common shares held 6,780 shares Common stock directly held after reported transactions

RSU-to-share ratio 1 share per RSU Each RSU settles into one share of common stock after vesting

Key Terms

restricted stock units (RSUs), Deferred Compensation Plan for Non-Employee Directors, Annual Meeting of Shareholders, grant, award, or other acquisition

4 terms

restricted stock units (RSUs) financial

"Each RSU represents the right to receive, after vesting and upon settlement, one share"

Restricted stock units (RSUs) are a type of company promise to give employees shares of stock in the future, usually after certain conditions like working for a set time. They are like a gift promised today that you receive later, which can become valuable if the company's stock price goes up. RSUs matter because they are a way companies reward employees and can be a significant part of compensation.

Deferred Compensation Plan for Non-Employee Directors financial

"pursuant to the Issuer's Deferred Compensation Plan for Non-Employee Directors"

Annual Meeting of Shareholders financial

"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, award, or other acquisition financial

"transaction_code_description: Grant, award, or other acquisition"

FAQ

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

What insider transaction did Terry Katharine report at SKWD?

Director Terry Katharine reported receiving a grant of 3,334 restricted stock units (RSUs) tied to Skyward Specialty Insurance Group common stock. The filing also shows she directly holds 6,780 common shares after the reported transactions.

When do Terry Katharine’s 3,334 RSUs at SKWD vest?

The 3,334 RSUs granted to Terry Katharine will fully vest on the date of Skyward Specialty Insurance Group’s 2027 Annual Meeting of Shareholders, subject to the terms of the RSU award agreement described in the filing.

How will Terry Katharine’s RSU award at SKWD be settled?

Each RSU gives Terry Katharine the right to receive one share of common stock after vesting and settlement. She has elected to defer settlement until her separation from Skyward Specialty Insurance Group under the company’s deferred compensation plan.

How many Skyward Specialty Insurance (SKWD) shares does Terry Katharine hold after this filing?

After the reported transactions, Terry Katharine directly holds 6,780 shares of Skyward Specialty Insurance Group common stock. In addition, she has an outstanding 2026 RSU award for 3,334 units linked to future common stock delivery.

What is the nature of the 2026 RSU award reported for SKWD?

The 2026 RSU Award consists of 3,334 restricted stock units granted to director Terry Katharine at a stated price of $0.00 per unit. The award is a grant/award acquisition rather than an open-market purchase or sale.

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

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Accepted by SEC EDGAR 05/08/2026 - 04:34 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^*

Terry Katharine

(Last) (First) (Middle)

800 GESSNER

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								6,780	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	(1)	05/06/2026		A		3,334		(2)(3)	(2)(3)	Common Stock	3,334	$0	3,334	D

Explanation of Responses:

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

2. 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.

3. The Reporting Person has elected to defer the settlement of this RSU award until their separation from the Company, pursuant to the Issuer's Deferred Compensation Plan for Non-Employee Directors.

	/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)