System1, Inc.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

(Amendment No. )

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Filed by a Party other than the Registrant ☐

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☐ Preliminary Proxy Statement

☐ Confidential, For Use of the Commission only (as permitted by Rule 14a-6(e)(2))

☒ Definitive Proxy Statement

☐ Definitive Additional Materials

☐ Soliciting Material Pursuant to §240.14a-2

System1, Inc.

(Name of Registrant as Specified in Its Charter)

Not Applicable

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

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4235 Redwood Avenue

Los Angeles, California 90066

LETTER TO STOCKHOLDERS

June 22, 2026

Dear Stockholder:

You are cordially invited to attend this year’s annual meeting of stockholders of System1, Inc. on Wednesday, July 22, 2026, at 11:00 a.m Pacific Time. The annual meeting will be a completely “virtual” meeting. You will be able to attend the annual meeting, as well as vote and submit your questions during the live webcast of the meeting, by visiting www.virtualshareholdermeeting.com/SST2026 and entering the company number and control number included on your proxy card or in the instructions that accompany your proxy materials.

Details regarding admission to the annual meeting and the business to be conducted at the annual meeting are described in the accompanying Notice of Annual Meeting of Stockholders and Proxy Statement.

Whether or not you plan to attend the annual meeting, your vote is very important and we encourage you to vote promptly. You may vote by either marking, signing and returning the enclosed proxy card or using telephone or internet voting. For specific instructions on voting, please refer to the instructions on your enclosed proxy card. If you attend the annual meeting you will have the right to revoke the proxy and vote your shares virtually at the meeting. If you hold your shares through an account with a brokerage firm, bank or other nominee, please follow the instructions you receive from your brokerage firm, bank or other nominee to vote your shares.

Sincerely yours,

/s/ Michael Blend

MICHAEL BLEND

CHAIRMAN AND CHIEF EXECUTIVE OFFICER

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

TO BE HELD JULY 22, 2026

This Proxy Statement and the proxy card are first being mailed to our stockholders on or about June 23, 2026. In accordance with Securities and Exchange Commission (“SEC”) rules, we are advising our stockholders of the Internet availability of our proxy materials related to our forthcoming Annual Meeting. Because we have elected to utilize the “full set delivery” of materials option, we are delivering paper copies of all of the proxy materials to all our stockholders, as well as providing access to those proxy materials on a publicly accessible website. This Proxy

Statement and our Annual Report on Form 10-K for the fiscal year ended December 31, 2025, as amended by Amendment No.1 on Form 10-K/A filed with the SEC on April 30, 2026 (collectively, our “Annual Report”) are available to our stockholders at https://ir.system1.com/financials/sec-filings/default.aspx. A copy of our Annual Report, as filed with the SEC, except for exhibits, will be furnished without charge to any of our stockholders upon written request to System1, Inc., 4235 Redwood Avenue, Los Angeles, California 90066 Attention: Corporate Secretary. This Proxy Statement and our Annual Report, are also available on the SEC’s website at www.sec.gov.

BY ORDER OF THE BOARD OF DIRECTORS

/s/ Michael Blend

MICHAEL BLEND

CHAIRMAN AND CHIEF EXECUTIVE OFFICER

Los Angeles, California

Dated: June 22, 2026

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