Orion180 Insurance owner buys 10,990 shares

The purchases included 1,000 shares at $8.92 on October 6, 2026, and 5,000 shares at $10.65 on September 22, 2026.

Rhea-AI Filing Summary

For Orion180 Insurance Group Inc. (OIG), Darling Strategic Investments LLC purchased 10,990 shares of Class A common stock in eight transactions from September 18 through October 6, 2026. Craig Darling and Darling Strategic Investments LLC are identified as 10 percent owners. Craig Darling is the LLC’s manager and has voting and investment power over the shares held by the LLC.

Insider Trade Summary

Net Buyer: 10,990 shares

Net Buy 8 txns

Insider Darling Craig, Darling Strategic Investments LLC

Role 10% Owner | 10% Owner

Bought 10,990 shs ($116K)

Type	Security	Shares	Price	Value
Purchase	Class A Common Stock F1	1,000	$8.92	$9K
Purchase	Class A Common Stock F1	1,900	$10.08	$19K
Purchase	Class A Common Stock F1	1,000	$11.11	$11K
Purchase	Class A Common Stock F1	990	$10.68	$11K
Purchase	Class A Common Stock F1	5,000	$10.65	$53K
Purchase	Class A Common Stock F1	500	$11.68	$6K
Purchase	Class A Common Stock F1	500	$11.56	$6K
Purchase	Class A Common Stock F1	100	$11.72	$1K

Holdings After Transaction: Class A Common Stock — 5,714,090 shares (Indirect, See Footnote)

Footnotes (1)

1. F1. 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.

Key Figures

Class A common shares purchased: 10,990 shares Shares purchased and price: 1,000 shares at $8.92 per share Shares purchased and price: 1,000 shares at $11.11 per share +2 more

5 metrics

Class A common shares purchased 10,990 shares Eight transactions from September 18 through October 6, 2026

Shares purchased and price 1,000 shares at $8.92 per share October 6, 2026

Shares purchased and price 1,000 shares at $11.11 per share September 22, 2026

Shares purchased and price 990 shares at $10.68 per share September 22, 2026

Shares purchased and price 5,000 shares at $10.65 per share September 22, 2026

Key Terms

Class A Common Stock, voting and investment power, private transaction

3 terms

Class A Common Stock financial

"shares of Class A Common Stock"

Class A common stock is a category of a company’s shares that carries a specific set of ownership rights—most commonly defined voting power and claims on dividends—set out in the company’s charter. For investors it matters because the class determines how much influence you have over corporate decisions, the share’s likely dividend and trading behavior, and how it compares in value to other share classes, like choosing a particular seat with different privileges at the company’s decision-making table.

voting and investment power financial

"has voting and investment power with respect to the shares"

private transaction financial

"Purchase in open market or private transaction"

A private transaction is the sale or transfer of securities, assets, or ownership stakes carried out directly between a small number of parties rather than on a public exchange. For investors it matters because these deals are less visible and often less liquid than public trades, so pricing can be harder to verify, the investment can be harder to sell quickly, and buyers or sellers may gain strategic advantages not available in open markets — like negotiated terms similar to a private garage sale versus a crowded marketplace.

FAQ

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

How many OIG shares did Darling Strategic Investments LLC buy?

Darling Strategic Investments LLC purchased 10,990 shares of OIG Class A common stock in eight transactions from September 18 through October 6, 2026.

What OIG share purchases did Darling Strategic Investments LLC make on September 22, 2026?

On September 22, 2026, Darling Strategic Investments LLC purchased 1,000 shares at $11.11 per share, 990 shares at $10.68 per share, and 5,000 shares at $10.65 per share.

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

Form 4 Insider Transactions: What Each Field Means →

See more from StockTitan in Google Search and AI answers. Adds StockTitan as a preferred source · opens Google

Add on Google Not now

Available on EDGAR 10/26/2026 - 05:05 PM EDT Accepted by SEC EDGAR 10/26/2026 - 05:05 PM EDT 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^*

Darling Craig

(Last) (First) (Middle)

200 MAR LEN DRIVE,

(Street)

MELBOURNE BEACH FLORIDA 32951

(City) (State) (Zip)

UNITED STATES

(Country)

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

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

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

2a. Foreign Trading Symbol

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

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

	Form filed by One Reporting Person
X	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
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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

1. Name and Address of Reporting Person^*

Darling Craig

(Last) (First) (Middle)

200 MAR LEN DRIVE,

(Street)

MELBOURNE BEACH FLORIDA 32951

(City) (State) (Zip)

UNITED STATES

(Country)

Relationship of Reporting Person(s) to Issuer

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

1. Name and Address of Reporting Person^*

Darling Strategic Investments LLC

(Last) (First) (Middle)

200 MAR LEN DRIVE,

(Street)

MELBOURNE BEACH FLORIDA 32951

(City) (State) (Zip)

UNITED STATES

(Country)

Relationship of Reporting Person(s) to Issuer

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

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).
** 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)