System1, Inc. — fact timeline

Robert Sharp was elected as director at System1, Inc..

“the holders of a majority of the outstanding Preferred Shares, acting by written consent pursuant to the Certificate of Designation, elected Robert Sharp to serve as a director of the Company, effective as of such date.”

System1, Inc. issued 39,250 shares of Series A Cumulative Convertible Preferred Stock of preferred stock to Participating Lenders for exchange for a portion of the Existing Loans; aggregate initial stated value of $39.3 million.

“the issuance of 39,250 shares of Series A Cumulative Convertible Preferred Stock (the “Preferred Shares”) to the Participating Lenders, with an aggregate initial stated value of $39.3 million (the “Share Consideration”)”

System1, Inc. entered into Exchange Agreement with Participating Lenders valued at $150.0 million term loan facility, 39,250 shares of Series A Cumulative Convertible Preferred Stock (effective 2026-05-29).

“On May 29, 2026 , S1 Holdings Finco, LLC, a Delaware limited liability company and a subsidiary of the Company (the “Priority Borrower”), and the Existing Borrower entered into that certain Exchange Agreement (the “Exchange Agreement”) with all of the Existing Term Lenders and the Existing Revolving Lenders (the “Participating Lenders”).”

System1, Inc. incurred term loan of $150.0 million with Participating Lenders at SOFR + 5.00% maturing January 2031.

“specified in the Exchange Agreement on the terms and subject to the conditions set forth therein. The consideration under the Exchange Agreement consists of (i) a new $150.0 million term loan facility held by the Participating Lenders (the “Priority Term Loans”), (ii) the issuance of 39,250 shares of Series A Cumulative Convertible Preferred Stock (the”

System1, Inc. reported first quarter ended March 31, 2026 results: revenue Revenue of $37.2 million, net income GAAP Net Loss of $57.6 million.

“System1 Announces First Quarter 2026 Financial Results • Revenue of $37.2 million • GAAP Gross Profit of $23.3 million, Margin of 63% • Adjusted Gross Profit of $28.2 million, Margin of 76% • GAAP Net Loss of $57.6 million • Adjusted EBITDA of $2.7 million”

System1, Inc. reported full year 2025 results: revenue $266.1 million, net income $81.2 million.

“Fiscal Year 2025 Financial Results: • Revenue Decreased 23% Over Prior Year to $266.1 million • Gross Profit Decreased 1% Over Prior Year to $100.4 million • Adjusted Gross Profit Increased 1% Over Prior Year to $153.4 million • Adjusted Gross Profit Margin Increased to 58% from 44% Year-Over-Year • GAAP Net Loss Decreased 17% Over Prior Year to $81.2 million • Adjusted EBITDA Increased 9% Over Prior Year to $41.9 million”

System1, Inc. reported fourth quarter 2025 results: revenue $51.9 million, net income $17.8 million.

“Fourth Quarter Financial Highlights: • Revenue Decreased 31% Over Prior Year to $51.9 million • Gross Profit Decreased 33% Over Prior Year to $21.3 million • Adjusted Gross Profit Decreased 22% Over Prior Year to $34.9 million • Adjusted Gross Profit Margin Increased to 67% from 59% Over Prior Year • GAAP Net Loss Decreased 1% Over Prior Year to $17.8 million • Adjusted EBITDA Decreased 54% Over Prior Year to $8.2 million”

System1, Inc. received a nyse deficiency notice notice regarding market value (rules 802.01B).

“December 8, 2025 System1, Inc. (the "Company") received a letter from the New York Stock Exchange (the "NYSE") notifying the Company that it is currently not in compliance with Section 802.01B of the NYSE Listed Company Manual because as of December 5, 2025, the Company’s 30 trading-day average market capitalization was less than $50 million and its last reported stockholder’s equity as of September 30, 2025 was less than $50 million. The Company has a period of 18 months to cure the market capitalization and/or stockholder’s equity deficiencies, subject to NYSE's approval of the Company’s bus”

System1, Inc.: Approved a 1-for-10 reverse stock split of Class A and Class C common stock via a certificate of amendment to the Certificate of Incorporation (effective 2025-06-12).

“the board of directors of the Company (the “Board”), after approval by a vote of security holders at the 2025 Annual Meeting as discussed under Item 5.07 of Company’s Current Report on Form 8-K filed June 10, 2025, approved a 1-for-10 reverse stock split (the “Reverse Stock Split”) of all issued and outstanding shares of the Company’s Class A common stock, par value $0.0001 per share (“Class A Common Stock”), and Class C common stock, par value $0.0001 per share (“Class C Common Stock” and, together with Class A Common Stock, “Common Stock”). The Company filed a certificate of amendment (the “Certificate of Amendment”) to its Certificate of Incorporation with the Secretary of State of the State of Delaware to effect the Reverse Stock Split, and the Company expects that its Class A Common Stock will begin trading on a split-adjusted basis at market open on June 12, 2025”

Jennifer Prince resigned as Director at System1, Inc..

“On April 15, 2025,Dexter Fowler and Jennifer Prince notified the Board of Directors (the “Board”) of System1, Inc. (the “Company”) of their respective resignation from the Board, effective as of the close of business on April 15, 2025.”

Dexter Fowler resigned as Director at System1, Inc..

“On April 15, 2025,Dexter Fowler and Jennifer Prince notified the Board of Directors (the “Board”) of System1, Inc. (the “Company”) of their respective resignation from the Board, effective as of the close of business on April 15, 2025.”

System1, Inc. received a nyse delisting notice notice regarding other (rules 802.01D).

“lue $0.0001 per share (the “Class A Common Stock”), at an exercise price of $11.50 per share, and listed to trade on the NYSE under the symbol “SST.WS” ("the Public Warrants") and (b) immediately suspend trading of the Public Warrants due to “abnormally low” selling price levels pursuant to Section 802.01D of the NYSE Listed Company Manual. To effect the delisting, the NYSE will apply to the Securities and Exchange Commission to delist the Public Warrants upon completion of all applicable procedures. Trading in the Company’s Class A Common Stock will be unaffected and will continue on the NYSE”

System1, Inc. received a nyse noncompliance notice notice regarding minimum bid price (rules 802.01C).

“January 6, 2025 System1, Inc. (the “Company”) was notified by the New York Stock Exchange (the “NYSE”) that it is not in compliance with Section 802.01C of the NYSE Listed Company Manual because the average closing price of the Company’s Class A Common Stock ("the Common Stock") was less than $1.00 over a consecutive 30 trading-day period. The notice does not result in the immediate delisting of the Company’s Common Stock from the NYSE. The Company plans to notify the NYSE by January 21, 2025 that it intends to cure the average closing stock price deficiency and to return to compliance with th”

System1, Inc. received a nyse noncompliance notice notice regarding minimum bid price (rules 802.01C).

“January 6, 2025 System1, Inc. (the “Company”) was notified by the New York Stock Exchange (the “NYSE”) that it is not in compliance with Section 802.01C of the NYSE Listed Company Manual because the average closing price”

System1, Inc. reported for its quarter ended March 31, 2024 results: revenue $84.9 Million, net income $14 Million.

“System1 Announces First Quarter 2024 Financial Results All Key Financial Results Above the High-End of Guidance Range • Revenue Decreased $11.2 Million Over Prior Quarter to $84.9 Million • Gross Profit Decreased 25% Over Prior Quarter to $18.6 Million • Adjusted Gross Profit Decreased 17% Over Prior Quarter to $31.2 Million • GAAP Net Loss Decreased 46% Over Prior Quarter to $14 Million”

Charles Ursini was appointed as President and Chief Operating Officer at System1, Inc..

“On April 23, 2024, the Board of Directors (the “Board”) of System, Inc. (the “Company”) appointed Charles Ursini, who was recently appointed to serve as a Class II director, as the Company’s President and Chief Operating Officer, in addition to continuing to serve on the Company’s Board.”

Ryan Caswell was appointed as Director at System1, Inc..

“On April 10, 2024, the Board of Directors (the “Board”) of System, Inc. (the “Company”) appointed Charles Ursini to serve as a Class II director and Ryan Caswell to serve as a Class III director of the Board.”

Charles Ursini was appointed as Director at System1, Inc..

“On April 10, 2024, the Board of Directors (the “Board”) of System, Inc. (the “Company”) appointed Charles Ursini to serve as a Class II director and Ryan Caswell to serve as a Class III director of the Board.”

System1, Inc. reported the quarter and year ended December 31, 2023 results: revenue $96.1 million, net income $25 million.

“Full Year 2023 Financial Results All Key Financial Results Above the High-End of Guidance Range Fourth Quarter Financial Highlights: • Revenue Increased 9% Over Prior Quarter to $96.1 million • Gross Profit Increased 1% Over Prior Quarter to $25 million • Adjusted Gross Profit Increased 1% Over Prior Quarter to $37.5 million • GAAP Net Loss Decreased 2% Over Prior”

System1, Inc. completed a disposition involving entities affiliated with Avance Investment Management, LLC and Just Develop It Limited for $240 million in cash, the return and subsequent cancellation of approximately 29 million shares of the Company's Class A common stock, and confirmation that cer (closed 2023-11-30).

“Purchasing Parties acquired all of the outstanding preference and ordinary shares of Total Security (the “Total Security Disposition”) for total consideration comprised of: (a) $240 million in cash, subject to certain adjustments set forth therein, (b) the return and subsequent cancellation of approximately 29 million shares of the Company’s Class A common stock,”

System1, Inc. entered into Share Purchase Agreement with JDI Antarctica Limited and JDI Antarctica Sub II Limited (the "Purchasing Parties") and entities affiliated with Avance Investment Management, LLC and Just Develop It Limited (the "Sponsor Parties") valued at $240 million in cash, subject to certain adjustments, and the return and subsequent cancellation of (effective 2023-11-30).

“pursuant to the terms of a share purchase agreement executed by and among the Company, Orchid Merger Sub II, LLC ("Orchid"), Sonic Newco, LLC ("Sonic" and, together with the Company and Orchid, the "Selling Parties"), JDI Antarctica Limited ("JDI Antarctica") and JDI Antarctica Sub II Limited ("JDI Sub" and, together with JDI Antarctica, the "Purchasing Parties") on November 30, 2023 (the "Share Purchase Agreement")”

Christopher Phillips resigned as Director at System1, Inc..

“the Phillips Resignation”

System1, Inc. incurred term loan of $10.0 million with Onyx Asset Finance Limited at 8.5% per annum maturing October 6, 2024.

“On October 6, 2023, Total Security Limited (“Total Security”), an indirect wholly-owned subsidiary of the Company, entered into a Secured Facility Agreement providing for a $10.0 million term loan (the “Secured Facility”) with Onyx Asset Finance Limited, a company organized under the laws of England & Wales (“Onyx” or the “Secured Lender”) and a subsidiary of Just Develop It Limited, one of the Company’s significant shareholders, in a private transaction approved by the independent and non-interested members of the Company’s Board.”

System1, Inc. incurred term loan of $2.5 million with Openmail2, LLC at SOFR plus 5.75% per annum maturing December 31, 2024.

“On October 6, 2023, Orchid Merger Sub II, LLC (“Orchid Sub”), a wholly-owned subsidiary of System1, Inc. (the “Company”), entered into a $2.5 million Term Loan Note (the “Term Note”) with Openmail2, LLC, a Delaware limited liability company (“OM2” or the “Term Lender”), which is principally owned and managed by trusts established for the benefit of the Company’s co-founders, Michael Blend and Charles Ursini, in a private transaction approved by the independent and non-interested members of the Company’s Board of Directors (the “Board”).”

System1, Inc. entered into Secured Facility Agreement with Onyx Asset Finance Limited valued at $10.0 million (effective 2023-10-06).

“Total Security Limited (“Total Security”), an indirect wholly-owned subsidiary of the Company, entered into a Secured Facility Agreement providing for a $10.0 million term loan (the “Secured Facility”) with Onyx Asset Finance Limited, a company organized under the laws of England & Wales (“Onyx” or the “Secured Lender”) and a subsidiary of Just Develop It Limited, one of the Company’s significant shareholders, in a private transaction approved by the independent and non-interested members of the Company’s Board.”

System1, Inc. entered into Term Loan Note with Openmail2, LLC valued at $2.5 million (effective 2023-10-06).

“Orchid Merger Sub II, LLC (“Orchid Sub”), a wholly-owned subsidiary of System1, Inc. (the “Company”), entered into a $2.5 million Term Loan Note (the “Term Note”) with Openmail2, LLC, a Delaware limited liability company (“OM2” or the “Term Lender”), which is principally owned and managed by trusts established for the benefit of the Company’s co-founders, Michael Blend and Charles Ursini, in a private transaction approved by the independent and non-interested members of the Company’s Board of Directors (the “Board”).”

System1, Inc. incurred loan of $5.2 million with Marc Mezzacca at Secured Overnight Financing Rate ("SOFR") as administered by the Federal Reserve.

“System1 entered into a $5.2 million Senior Unsecured Promissory Note with the Lender party thereto.”

Tanmay Kumar was appointed as Director at System1, Inc..

“Tanmay Kumar to serve as a Class III director”

Taryn Naidu was appointed as Director at System1, Inc..

“appointed Taryn Naidu to serve as a Class I director”

System1, Inc. reported second half of 2023 results: revenue $289 million to $297 million. Guidance initiated.

“Company Provides Second Half 2023 Guidance of: $289 Million to $297 Million of Revenue and $35 Million to $40 Million of Adjusted EBITDA”

System1, Inc. reported quarter ended June 30, 2023 results: revenue $147 million, net income $44 million.

“System1 Announces Second Quarter 2023 Financial Results • Revenue Decreased 33% Year-Over-Year to $147 Million • Gross Profit Decreased 26% Year-Over-Year to $41 Million • Adjusted Gross Profit Decreased 21% Year-Over-Year to $53 Million • GAAP Net Loss of $44 Million • Adjusted EBITDA of $15 Million • Company Provides Second Half 2023 Guidance of: $289 Million to $297 Million of Revenue and $35 Million to $40 Million of Adjusted EBITDA”

Ryan Caswell resigned as Director at System1, Inc..

“On August 1, 2023, Ryan Caswell notified the Board of Directors (the “Board”) of System1, Inc. of his resignation from the Board, effective as of the close of business on August 1, 2023.”

System1, Inc. shareholders approved Ratification of the Independent Registered Public Accounting Firm at the 2023-06-19 meeting.

“Proposal 2 - Ratification of the Independent Registered Public Accounting Firm Proposal 2 was a management proposal to ratify the appointment of PricewaterhouseCoopers LLP to serve as the Company’s independent registered public accounting firm for the fiscal year ending December 31, 2023. This proposal was approved. Votes For Votes Against Votes Abstained/Withheld Broker Non-Votes 94,149,168 22,986 454,351”

System1, Inc. shareholders approved Election of Class I Directors at the 2023-06-19 meeting.

“Proposal 1 - Election of Class I Directors The individuals listed below were each elected to serve on the Company’s Board for a three-year term expiring at the Company’s 2026 Annual Meeting of Stockholders, or until his or her successor is duly elected and qualified. Nominee for Director Votes For Votes Against Votes Abstained/Withhold Broker Non-Votes Dexter Fowler 94,533,650 0 92,855 Caroline Horn 93,977,543 0 648,962 Jennifer Prince 94,977,543 0 88,973”

Ryan Caswell was appointed as Director at System1, Inc..

“the remaining members of the Board appointed Ryan Caswell to fill the current vacancy on the Board as a Class III Director effective immediately”

System1, Inc. reported FY 2022 results: revenue Revenue in the predecessor period was $53 million and revenue in the successor period was $774 million, net income Net loss in the predecessor period was $37 million and net loss in the successor period was $442 million.

“FY 2022 Financial Highlights Exhibit 99.1 • Revenue in the predecessor period was $53 million and revenue in the successor period was $774 million, compared to $688 million in the prior year. Gross profit in the predecessor period was $6 million and gross profit in the successor period was $189 million, compared to $163 million in the prior year. • Adjusted Gross Profit in the predecessor period was $11 million and adjusted Gross Profit in the successor period was $235 million, compared to $167 million in the prior year. • Net loss in the predecessor period was $37 million and net loss in the successor period was $442 million, compared to net income of $33 million in the prior year.”

System1, Inc. reported Fourth Quarter 2022 results: revenue $187 million, net income Net loss of $51 million.

“Fourth Quarter 2022 Financial Highlights • Revenue decreased 7% year-over-year to $187 million compared to $200 million in the prior year. • Gross profit increased 6% year-over-year to $47 million. • Adjusted Gross Profit increased 31% year-over-year to $59 million compared to $45 million in the prior year. • Net loss of $51 million, compared to $3 million of net income in the prior year.”

System1, Inc. incurred revolving credit of $20.0 million with Lone Star Friends Trust and CEE Holding Trust at SOFR plus 3.15% maturing July 10, 2024.

“Orchid Sub entered into a $20.0 million Revolving Note with the Lenders party thereto”

System1, Inc. entered into Revolving Note with Lone Star Friends Trust and CEE Holding Trust valued at $20.0 million (effective 2023-04-10).

“On April 10, 2023, Orchid Merger Sub II, LLC (“Orchid Sub”), a wholly-owned subsidiary of System1, Inc. (the “Company”), entered into a $20.0 million Revolving Note (the “Revolving Note”) with Lone Star Friends Trust (acting by and through its trustee, Stanley Blend, “Lone Star”) and CEE Holding Trust (acting by and through its trustee, Jackson Hole Trust Company, “CEE”, and together with Lone Star, collectively, the “Lenders” and each, a “Lender”)”

System1, Inc. received a nyse deficiency notice notice regarding late filing (rules 802.01E).

“April 3, 2023, System1, Inc. (the “Company”) received a notice letter (the “Notice”) from the NYSE Regulation Department (the “Staff”) of the New York Stock Exchange (“NYSE”) notifying the Company that, based upon the Company’s failure to timely file its Annual Report on Form 10-K for the fiscal year ended December 31, 2022 (the “Annual Report”), it was not in compliance with the NYSE’s continued listing requirements. Specifically, Section 802.01E of the NYSE Listed Company Manual provides that an NYSE-listed company is not in compliance if it does not timely file its annual and interim report”

Richard Massey was appointed as Class III Director at System1, Inc..

“On March 21, 2023, following Mr. Foley’s resignation, the remaining members of the Board appointed Richard Massey to replace Mr. Foley as a Class III Director effective immediately, serving in the class of directors whose term expires at the Company’s 2025 annual meeting of stockholders.”

William P. Foley, II resigned as Director at System1, Inc..

“On March 15, 2023, William P. Foley, II. notified the Board of Directors (the “Board”) of System1, Inc. (the “Company”) of his resignation from the Board, effective as of March 15, 2023.”

System1, Inc. reported that prior financial statements should not be relied upon.

“As a result, management of the Company and the Audit Committee determined that the previously issued condensed consolidated quarterly financial statements included in the Q1 2022 Form 10-Q, Q2 2022 Form 10-Q and Q3 2022 Form 10-Q, were materially misstated and accordingly each require restatement and should no longer be relied upon.”

System1, Inc.: Amended and restated bylaws to address universal proxy rules and enhance procedural mechanics and disclosure requirements for stockholder nominations and proposals (effective 2023-02-23).

“On February 23, 2023, the Board of Directors (the “Board”) of System1, Inc. (the “Company”) approved and adopted amended and restated bylaws (the “Amended and Restated Bylaws”), to, among other things: • address the universal proxy rules adopted by the U.S. Securities and Exchange Commission (the “SEC”), by clarifying that no person may solicit proxies in support of a director nominee other than the Board’s nominees unless such person has complied with Rule 14a-19 under the Securities Exchange Act of 1934, as amended, including the applicable notice and solicitation requirements; and • enhance procedural mechanics and disclosure requirements in connection with stockholder nominations of directors and submissions of proposals regarding other business at stockholder meetings, including requiring additional background information and disclosures regarding proposing stockholders, proposed nominees and business, and other persons related to a stockholder’s solicitation of proxies.”

System1, Inc. reported full year 2022 results: revenue $830 Million to $845 Million.

“Company Updates Full-Year 2022 Guidance: $830 Million to $845 Million of Revenue, $255 Million to $260 Million of Adjusted Gross Profit and $125 Million to $130 Million of Adjusted EBITDA”

System1, Inc. reported the quarter ended September 30, 2022 results: revenue $201 million, net income Net loss of $38 million.

“Revenue Grew 17% Year-Over-Year to $201 Million • Gross Profit Grew 21% Year-Over-Year to $50 Million • Adjusted Gross Profit Grew 49% Year-Over-Year to $63 Million • Net Loss of $38 Million • Adjusted EBITDA increased 28% to $29 Million Compared to $23 Million in the Prior Year”

Paul Filsinger resigned as President at System1, Inc..

“On November 2, 2022, Paul Filsinger, President of System1, Inc. (the “Company”), notified the Company that he is resigning from his position as the Company’s President effective as of the close of business on November 30, 2022, in order to pursue other opportunities.”

John Civantos was appointed as Director at System1, Inc..

“the Board, effective February 25, 2022, appointed John Civantos as the ninth (9 th ) director of the Company to fill the vacancy on the Board created by the expansion of the Board described above.”