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SEC FORM 4SEC 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

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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^*

Darling Craig

(Last)

(First)

(Middle)

200 MAR LEN DRIVE,

(Street)

MELBOURNE BEACH

32951

(City)

(State)

(Zip)

2. Issuer Name and Ticker or Trading Symbol
Orion180 Insurance Group Inc. [ OIG ]
Foreign Trading Symbol

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
09/18/2026

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

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

	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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Class A Common Stock	09/18/2026		P		100	A	$11.72	5,703,200	I	See Footnote⁽¹⁾
Class A Common Stock	09/21/2026		P		500	A	$11.68	5,703,700	I	See Footnote⁽¹⁾
Class A Common Stock	09/21/2026		P		500	A	$11.56	5,704,200	I	See Footnote⁽¹⁾
Class A Common Stock	09/22/2026		P		1,000	A	$11.11	5,705,200	I	See Footnote⁽¹⁾
Class A Common Stock	09/22/2026		P		990	A	$10.68	5,706,190	I	See Footnote⁽¹⁾
Class A Common Stock	09/22/2026		P		5,000	A	$10.65	5,711,190	I	See Footnote⁽¹⁾
Class A Common Stock	09/23/2026		P		1,900	A	$10.08	5,713,090	I	See Footnote⁽¹⁾
Class A Common Stock	10/06/2026		P		1,000	A	$8.92	5,714,090	I	See Footnote⁽¹⁾

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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

1. Name and Address of Reporting Person^*

Darling Craig

(Last)

(First)

(Middle)

200 MAR LEN DRIVE,

(Street)

MELBOURNE BEACH

32951

(City)

(State)

(Zip)

1. Name and Address of Reporting Person^*

Darling Strategic Investments LLC

(Last)

(First)

(Middle)

200 MAR LEN DRIVE,

(Street)

MELBOURNE BEACH

32951

(City)

(State)

(Zip)

Explanation of Responses:

1. The securites reported herein are held by Darling Strategic Investments LLC. Craig Darling is the manager of Darling Strategic Investments LLC and in such capacity has voting and investment power with respect to the shares held by Darling Strategic Investments LLC.

	/s/ Craig Darling	10/26/2026
	Darling Strategic Investments LLC, By: /s/ Craig Darling, Manager	10/26/2026
	** 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).
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