[Form 4] System1, Inc. Insider Trading Activity

Rhea-AI Filing Summary

System1, Inc. (SST) director CEE Holdings Trust, via Jackson Hole Trust Company, reported three open-market purchases of Class A common stock on 08/19/2025, 08/20/2025 and 08/21/2025. The filings show 6,567 shares purchased at a weighted average $6.32 on 08/19/2025, 12,584 shares at $6.25 on 08/20/2025, and 12,584 shares at $6.90 on 08/21/2025. After these transactions the reporting person beneficially owned 908,540 Class A shares, reflecting post-transaction totals that account for a 1-for-10 reverse stock split completed June 11, 2025. Footnotes note the reported prices are weighted averages across multiple trades.

Positive

• Repeated insider purchases on 08/19/2025, 08/20/2025 and 08/21/2025 totaling 31,735 shares purchased
• Beneficial ownership increased to 908,540 Class A shares after transactions
• Complete disclosure including weighted-average price footnotes and reverse split adjustment

Negative

• None.

Insights

Financial Analyst

TL;DR: Director purchases totaling 31,735 shares raise insider ownership to 908,540 shares, signaling managerial confidence.

The reported open-market purchases across three days amount to 31,735 Class A shares acquired at weighted average prices between $6.25 and $6.90, bringing beneficial ownership to 908,540 shares after the issuer's 1-for-10 reverse split. For investors, repeated insider buying over consecutive days is often interpreted as a positive signal about management's view of valuation. The transactions were relatively small in isolation but meaningful when aggregated and disclosed by a director. No sales, option exercises, or derivative transactions are reported.

Corporate Governance Expert

TL;DR: A director increased holdings through lawful open-market purchases; disclosures appear complete with weighted-price footnotes.

The Form 4 discloses direct purchases reported by a trustee acting for CEE Holdings Trust and includes required explanatory footnotes on weighted-average pricing and the June 11 reverse split. The signature is provided by a senior trust officer. From a governance standpoint, the filing meets disclosure norms and shows alignment of a board-affiliated holder with shareholder interests through incremental purchases. There are no indications of planned trading arrangements or derivative activity disclosed on this form.

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

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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^*

CEE Holdings Trust

(Last) (First) (Middle)

C/O JACKSON HOLE TRUST COMPANY

185 W. BROADWAY, SUITE 101

(Street)

JACKSON HOLE WY 83001

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
System1, Inc. [ SST ]

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

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

3. Date of Earliest Transaction (Month/Day/Year)
08/19/2025

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
Class A Common Stock	08/19/2025		P		6,567	A	$6.32(1)	883,372(2)	D
Class A Common Stock	08/20/2025		P		12,584	A	$6.25(3)	895,956	D
Class A Common Stock	08/21/2025		P		12,584	A	$6.9(4)	908,540	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. The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $6.20 to $6.50, inclusive. The Reporting Person(s) undertake(s) to provide to the Issuer, any security holder, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

2. Represents the total number of shares held after the Issuer's completion of a 1-for-10 reverse stock split that occurred on June 11, 2025.

3. The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $6.13 to $6.50, inclusive. The Reporting Person(s) undertake(s) to provide to the Issuer, any security holder, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

4. The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $6.50 to $6.92, inclusive. The Reporting Person(s) undertake(s) to provide to the Issuer, any security holder, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

Remarks:

	/s/ Brittany Gale, Senior Trust Officer of Jackson Hole Trust Company, Trustee	08/21/2025
	** 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 transactions did System1 (SST) director CEE Holdings Trust report on the Form 4?

The Form 4 reports three open-market purchases of Class A common stock: 6,567 shares on 08/19/2025, 12,584 shares on 08/20/2025, and 12,584 shares on 08/21/2025.

How many shares does the reporting person own after the reported transactions?

Following the reported purchases the reporting person beneficially owned 908,540 Class A shares, adjusted for a 1-for-10 reverse split completed June 11, 2025.

What prices were paid for the shares in the reported transactions?

The filings disclose weighted-average prices: $6.32 on 08/19/2025, $6.25 on 08/20/2025, and $6.90 on 08/21/2025, with footnotes noting ranges across multiple trades.

Do the Form 4 disclosures include derivative transactions or sales?

No. The Form 4 shows only non-derivative purchases of Class A common stock; no derivative securities or sales are reported in this filing.

Who signed the Form 4 for the reporting person?

The Form 4 was signed by Brittany Gale, Senior Trust Officer of Jackson Hole Trust Company, Trustee on 08/21/2025.