Document

We have acted as counsel to System1, Inc., a Delaware corporation (the “Company”), in connection with the preparation and filing with the Securities and Exchange Commission of the Company’s Registration Statement on Form S-3 (the “Registration Statement”), pursuant to the Securities Act of 1933, as amended (the “Act”), relating to the offer and sale by the selling stockholders named in the prospectus contained in the Registration Statement (the “Selling Stockholders”) from time to time of up to an aggregate of 5,287,321 shares (the “Shares”) of Class A common stock, par value $0.0001 per share (the “Class A Common Stock”), of the Company issuable upon conversion of the Company’s Series A Cumulative Convertible Preferred Stock, par value $0.0001 per share (the “Series A Preferred Stock”), which includes shares of Class A Common Stock issuable upon conversion of the Series A Preferred Stock in respect of accrued PIK Dividends. Capitalized terms defined in the Registration Statement and used (but not otherwise defined) herein are used herein as so defined.

In so acting, we have examined originals or copies (certified or otherwise identified to our satisfaction) of (i) Certificate of Incorporation of the Company filed with the Secretary of State of the State of Delaware, as amended by the Certificates of Amendment to Certificate of Incorporation of the Company, incorporated by reference as Exhibits 3.1, 3.2 and 3.3, respectively, to the Registration Statement; (ii) the Second Amended and Restated Bylaws of the Company, incorporated by reference as Exhibit 3.4 to the Registration Statement; (iii) the Certificate of Designation of Series A Preferred Stock of the Company filed with the Secretary of State of the State of Delaware, incorporated by reference as Exhibit 3.5 to the Registration Statement; (iv) the Registration Statement; (v) the prospectus contained within the Registration Statement; and (vi) such corporate records, agreements, documents and other instruments, and such certificates or comparable documents of public officials and of officers and representatives of the Company, and have made such inquiries of such officers and representatives, as we have deemed relevant and necessary as a basis for the opinions hereinafter set forth.

In such examination, we have assumed the genuineness of all signatures, the legal capacity of all natural persons, the authenticity of all documents submitted to us as originals, the conformity to original documents of all documents submitted to us as certified, conformed or photostatic copies and the authenticity of the originals of such latter documents. As to all questions of fact material to these opinions that have not been independently established, we have relied upon certificates or comparable documents of officers and representatives of the Company.

We express no opinion to the extent that future issuances of securities of the Company, and/or anti-dilution adjustments to outstanding securities of the Company, including the Series A Preferred Shares and the Shares, may cause the Series A Preferred Shares to be convertible into more shares of Class A Common Stock than the number that then remain authorized but unissued. We have assumed that at or prior to the time of the delivery of any of the Shares, the Registration Statement will have been declared effective under the Act, and no stop orders suspending the Registration Statement’s effectiveness will have been issued and remain in effect.

Based on the foregoing, and subject to the qualifications stated herein, we are of the opinion that the Shares have been duly authorized and, when issued upon conversion of the Series A Preferred Stock in accordance with the terms of the Certificate of Designation, will be validly issued, fully paid and nonassessable.

We hereby consent to the filing of this letter as an exhibit to the Registration Statement and to the reference to our firm under the caption “Legal Matters” in the prospectus which is a part of the Registration Statement. In giving such consent, we do not hereby admit that we are in the category of persons whose consent is required under Section 7 of the Act or the rules and regulations of the Securities and Exchange Commission.