SST

SEC source: 0001912571-24-000007 · wk-form4_1723682861.xml · nonDerivative · entry 2

Blend Stanley · CIK 0001912571 · 10% owner

Lone Star Friends Trust · CIK 0001909643 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust (The Nola Delfina Blend Trust)

Disclosed balance after: 1,517,622

F1 · kind: The Lone Star Friends Trust made a deemed distribution of 1,850,215 shares of Class A common stock to its beneficiaries (which included Mr. Michael Blend, the Issuer's co-founder and CEO, and his spouse). The beneficiaries of the Lone Star Friends Trust immediately made a gift of 925,107 and 925,108 shares of Class A common stock to each of the Dante Jacob Blend Trust and the Nola Deflina Blend Trust, respectively, (which are trusts established for the benefit of the beneficiaries children). The Reporting Person is the Trustee of each of the Lone Star Friends Trust, the Dante Jacob Blend Trust and the Nola Delfina Blend Trust.

F1 · shares: The Lone Star Friends Trust made a deemed distribution of 1,850,215 shares of Class A common stock to its beneficiaries (which included Mr. Michael Blend, the Issuer's co-founder and CEO, and his spouse). The beneficiaries of the Lone Star Friends Trust immediately made a gift of 925,107 and 925,108 shares of Class A common stock to each of the Dante Jacob Blend Trust and the Nola Deflina Blend Trust, respectively, (which are trusts established for the benefit of the beneficiaries children). The Reporting Person is the Trustee of each of the Lone Star Friends Trust, the Dante Jacob Blend Trust and the Nola Delfina Blend Trust.

F3 · ownership.nature: Reflects securities held by the Nola Delfina Blend Trust (the "Nola Trust"). Mr. Blend is the Trustee of the Nola Trust, with sole voting and dispositive power over the assets of Nola Trust.

SEC source: 0001912571-24-000007 · wk-form4_1723682861.xml · nonDerivative · entry 1

Blend Stanley · CIK 0001912571 · 10% owner

Lone Star Friends Trust · CIK 0001909643 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust (Lone Star Friends Trust)

Disclosed balance after: 0

F1 · kind: The Lone Star Friends Trust made a deemed distribution of 1,850,215 shares of Class A common stock to its beneficiaries (which included Mr. Michael Blend, the Issuer's co-founder and CEO, and his spouse). The beneficiaries of the Lone Star Friends Trust immediately made a gift of 925,107 and 925,108 shares of Class A common stock to each of the Dante Jacob Blend Trust and the Nola Deflina Blend Trust, respectively, (which are trusts established for the benefit of the beneficiaries children). The Reporting Person is the Trustee of each of the Lone Star Friends Trust, the Dante Jacob Blend Trust and the Nola Delfina Blend Trust.

F1 · shares: The Lone Star Friends Trust made a deemed distribution of 1,850,215 shares of Class A common stock to its beneficiaries (which included Mr. Michael Blend, the Issuer's co-founder and CEO, and his spouse). The beneficiaries of the Lone Star Friends Trust immediately made a gift of 925,107 and 925,108 shares of Class A common stock to each of the Dante Jacob Blend Trust and the Nola Deflina Blend Trust, respectively, (which are trusts established for the benefit of the beneficiaries children). The Reporting Person is the Trustee of each of the Lone Star Friends Trust, the Dante Jacob Blend Trust and the Nola Delfina Blend Trust.

F2 · ownership.nature: Reflects securities held by the Lone Star Friends Trust ("Lone Star"). Mr. Blend is the Trustee of Lone Star, with sole voting and dispositive power over the assets of Lone Star.

SEC source: 0001906862-24-000009 · wk-form4_1722472567.xml · nonDerivative · entry 1

Kidambi Tridivesh · CIK 0001906862 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 740,077

F1 · shares: Upon the vesting of 6,250 restricted stock units ("RSUs") previously granted to the Reporting Person, the Company withheld 2,231 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 137,500 unvested RSUs.

SEC source: 0001906904-24-000015 · wk-form4_1722472527.xml · nonDerivative · entry 1

Coppola Brian · CIK 0001906904 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 305,588

F1 · shares: Upon the vesting of 4,688 restricted stock units ("RSUs") previously granted to the Reporting Person, the Company withheld 2,048 shares to cover the Reporting Person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 124,757 unvested RSUs.

SEC source: 0001907144-24-000010 · wk-form4_1722472493.xml · nonDerivative · entry 1

Robinson Jennifer Lynn · CIK 0001907144 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 164,572

F1 · shares: Upon the vesting of 6,281 restricted stock units ("RSUs") previously granted to the Reporting Person, the Company withheld 3,185 shares to cover the Reporting Person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 42,035 unvested RSUs.

SEC source: 0001907093-24-000014 · wk-form4_1722472449.xml · nonDerivative · entry 1

Sestanovich Elizabeth · CIK 0001907093 · Chief People Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 224,722

F1 · shares: Upon the vesting of 3,750 restricted stock units ("RSUs") previously granted to the Reporting Person, the Company withheld 1,338 shares to cover the Reporting Person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 104,711 unvested RSUs.

SEC source: 0001624457-24-000015 · wk-form4_1722472409.xml · nonDerivative · entry 1

Weinrot Daniel J · CIK 0001624457 · General Counsel & Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 211,565

F1 · shares: Upon the vesting of 3,750 restricted stock units ("RSUs") previously granted to the Reporting Person, the Company withheld 1,901 shares to cover the Reporting Person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 106,184 unvested RSUs.

SEC source: 0001906862-24-000006 · wk-form4_1721694793.xml · nonDerivative · entry 1

Kidambi Tridivesh · CIK 0001906862 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 742,308

F1 · shares: The Reporting Person was granted 100,000 restricted stock units ("RSUs") in connection with his continued employment with System1, Inc. ("SST"). Each RSU represents the right to receive one share of SST Class A Common Stock upon vesting. Subject to the continued employment of the Reporting Person through the applicable vesting date, one-third of the RSUs will vest on January 15, 2025, and the remaining two-thirds will vest in 8 substantially equal quarterly installments on each quarterly anniversary thereafter.

F2 · balance_after: The amount of securities beneficially owned following the reported transaction has been updated to correct a previous overstatement of such beneficially owned shares by 34,604 shares of Class A Common Stock, and the amount of beneficially owned shares following the reported transaction has been reduced accordingly.

F3 · balance_after: Includes 143,750 unvested RSUs.

SEC source: 0001907093-24-000012 · wk-form4_1721694746.xml · nonDerivative · entry 1

Sestanovich Elizabeth · CIK 0001907093 · Chief People Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 226,060

F1 · shares: The Reporting Person was granted 80,000 restricted stock units ("RSUs") in connection with her continued employment with System1, Inc. ("SST"). Each RSU represents the right to receive one share of SST Class A Common Stock upon vesting. Subject to the continued employment of the Reporting Person through the applicable vesting date, one-third of the RSUs will vest on January 15, 2025, and the remaining two-thirds will vest in 8 substantially equal quarterly installments on each quarterly anniversary thereafter.

F2 · balance_after: Includes 108,461 unvested RSUs.

SEC source: 0001906904-24-000013 · wk-form4_1721694706.xml · nonDerivative · entry 1

Coppola Brian · CIK 0001906904 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 307,636

F1 · shares: The Reporting Person was granted 90,000 restricted stock units ("RSUs") in connection with his continued employment with System1, Inc. ("SST"). Each RSU represents the right to receive one share of SST Class A Common Stock upon vesting. Subject to the continued employment of the Reporting Person through the applicable vesting date, one-third of the RSUs will vest on January 15, 2025, and the remaining two-thirds will vest in 8 substantially equal quarterly installments on each quarterly anniversary thereafter.

F2 · balance_after: Includes 129,445 unvested RSUs.

SEC source: 0001624457-24-000013 · wk-form4_1721694665.xml · nonDerivative · entry 1

Weinrot Daniel J · CIK 0001624457 · General Counsel & Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 213,466

F1 · shares: The Reporting Person was granted 80,000 restricted stock units ("RSUs") in connection with his continued employment with System1, Inc. ("SST"). Each RSU represents the right to receive one share of SST Class A Common Stock upon vesting. Subject to the continued employment of the Reporting Person through the applicable vesting date, one-third of the RSUs will vest on January 15, 2025, and the remaining two-thirds will vest in 8 substantially equal quarterly installments on each quarterly anniversary thereafter.

F2 · balance_after: Includes 109,934 unvested RSUs.

SEC source: 0001624457-24-000011 · wk-form4_1721261742.xml · nonDerivative · entry 1

Weinrot Daniel J · CIK 0001624457 · General Counsel & Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 133,466

F1 · shares: Upon the vesting of 1,842 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 934 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 29,934 unvested RSUs.

SEC source: 0001907093-24-000010 · wk-form4_1721261625.xml · nonDerivative · entry 1

Sestanovich Elizabeth · CIK 0001907093 · Chief People Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 146,060

F1 · shares: Upon the vesting of 1,105 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 395 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 28,461 unvested RSUs.

SEC source: 0001906904-24-000011 · wk-form4_1721261587.xml · nonDerivative · entry 1

Coppola Brian · CIK 0001906904 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 217,636

F1 · shares: Upon the vesting of 3,315 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 1,448 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 39,445 unvested RSUs.

SEC source: 0002012590-24-000016 · wk-form4_1720734363.xml · nonDerivative · entry 3

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,625,096

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F2 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.43 to $1.45, 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.

SEC source: 0002012590-24-000016 · wk-form4_1720734363.xml · nonDerivative · entry 2

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,618,347

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F3 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.40 to $1.45, 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.

SEC source: 0002012590-24-000016 · wk-form4_1720734363.xml · nonDerivative · entry 1

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,551,161

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F2 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.43 to $1.45, 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.

SEC source: 0002012590-24-000014 · wk-form4_1720485200.xml · nonDerivative · entry 2

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,505,545

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

SEC source: 0002012590-24-000014 · wk-form4_1720485200.xml · nonDerivative · entry 1

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,503,190

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F2 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.44 to $1.45, 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.

SEC source: 0002012590-24-000012 · wk-form4_1719964677.xml · nonDerivative · entry 3

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,502,942

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F4 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.40 to $1.45, 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.

SEC source: 0002012590-24-000012 · wk-form4_1719964677.xml · nonDerivative · entry 2

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,427,836

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F3 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.41 to $1.45, 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.

SEC source: 0001628280-24-031217 · wk-form4_1720055286.xml · derivative · entry 1

Sestanovich Elizabeth · CIK 0001907093 · Chief People Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 450,000

Underlying: Class A Common Stock · 450,000 shares

Expires 2031-07-01

F1 · security: These stock appreciation rights (these "SARs") were granted to the Reporting Person pursuant to the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and a corresponding Stock Appreciation Rights Grant Notice and Award Agreement between System1, Inc. (the "Issuer") and the Reporting Person. The SARs reported on this Form 4 represent the right to receive (at the Issuer's discretion), upon exercise of the SARs by the Reporting Person, a payment in either (x) Class A Common Stock, par value $0.0001 per share ("Class A Common Stock") or (y) cash, in the amount equal to the number of shares of Class A Common Stock underlying the number of SARs being exercised multiplied by the excess of the fair market value of one share of Class A Common Stock on (i) the date the SARs are exercised, and (ii) $1.44, the Issuer's closing price on July 1, 2024 (the date the SARs were granted, the "Grant Date").

F2 · derivative.exercise_date: These Stock Appreciation Rights ("SARs") were granted to the Reporting Person on July 1, 2024 under the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and vest (i) 25% upon the Issuer first achieving trailing twelve month Adjusted EBITDA ("TTM Adjusted EBITDA") of $50.0 million after the date of grant, (ii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $60.0 million after the date of grant, (iii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $70.0 million after the date of grant and (iv) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $80.0 million after the date of grant, in each case, subject to the terms of the Plan and an award agreement entered into between the Reporting Person and the Issuer pursuant to the Plan.

SEC source: 0001628280-24-031216 · wk-form4_1720055249.xml · derivative · entry 1

Coppola Brian · CIK 0001906904 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 475,000

Underlying: Class A Common Stock · 475,000 shares

Expires 2031-07-01

F1 · security: These stock appreciation rights (these "SARs") were granted to the Reporting Person pursuant to the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and a corresponding Stock Appreciation Rights Grant Notice and Award Agreement between System1, Inc. (the "Issuer") and the Reporting Person. The SARs reported on this Form 4 represent the right to receive (at the Issuer's discretion), upon exercise of the SARs by the Reporting Person, a payment in either (x) Class A Common Stock, par value $0.0001 per share ("Class A Common Stock") or (y) cash, in the amount equal to the number of shares of Class A Common Stock underlying the number of SARs being exercised multiplied by the excess of the fair market value of one share of Class A Common Stock on (i) the date the SARs are exercised, and (ii) $1.44, the Issuer's closing price on July 1, 2024 (the date the SARs were granted, the "Grant Date").

F2 · derivative.exercise_date: These Stock Appreciation Rights ("SARs") were granted to the Reporting Person on July 1, 2024 under the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and vest (i) 25% upon the Issuer first achieving trailing twelve month Adjusted EBITDA ("TTM Adjusted EBITDA") of $50.0 million after the date of grant, (ii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $60.0 million after the date of grant, (iii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $70.0 million after the date of grant and (iv) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $80.0 million after the date of grant, in each case, subject to the terms of the Plan and an award agreement entered into between the Reporting Person and the Issuer pursuant to the Plan.

SEC source: 0001628280-24-031215 · wk-form4_1720055217.xml · derivative · entry 1

Ursini Charles · CIK 0002018813 · Director · President & COO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,500,000

Underlying: Class A Common Stock · 2,500,000 shares

Expires 2031-07-01

F1 · security: These stock appreciation rights (these "SARs") were granted to the Reporting Person pursuant to the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and a corresponding Stock Appreciation Rights Grant Notice and Award Agreement between System1, Inc. (the "Issuer") and the Reporting Person. The SARs reported on this Form 4 represent the right to receive (at the Issuer's discretion), upon exercise of the SARs by the Reporting Person, a payment in either (x) Class A Common Stock, par value $0.0001 per share ("Class A Common Stock") or (y) cash, in the amount equal to the number of shares of Class A Common Stock underlying the number of SARs being exercised multiplied by the excess of the fair market value of one share of Class A Common Stock on (i) the date the SARs are exercised, and (ii) $1.44, the Issuer's closing price on July 1, 2024 (the date the SARs were granted, the "Grant Date").

F2 · derivative.exercise_date: These Stock Appreciation Rights ("SARs") were granted to the Reporting Person on July 1, 2024 under the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and vest (i) 25% upon the Issuer first achieving trailing twelve month Adjusted EBITDA ("TTM Adjusted EBITDA") of $50.0 million after the date of grant, (ii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $60.0 million after the date of grant, (iii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $70.0 million after the date of grant and (iv) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $80.0 million after the date of grant, in each case, subject to the terms of the Plan and an award agreement entered into between the Reporting Person and the Issuer pursuant to the Plan.

SEC source: 0001628280-24-031214 · wk-form4_1720055177.xml · derivative · entry 1

Blend L Michael · CIK 0001504477 · Director · CEO & Chairman

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,500,000

Underlying: Class A Common Stock · 2,500,000 shares

Expires 2031-07-01

F1 · security: These stock appreciation rights (these "SARs") were granted to the Reporting Person pursuant to the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and a corresponding Stock Appreciation Rights Grant Notice and Award Agreement between System1, Inc. (the "Issuer") and the Reporting Person. The SARs reported on this Form 4 represent the right to receive (at the Issuer's discretion), upon exercise of the SARs by the Reporting Person, a payment in either (x) Class A Common Stock, par value $0.0001 per share ("Class A Common Stock") or (y) cash, in the amount equal to the number of shares of Class A Common Stock underlying the number of SARs being exercised multiplied by the excess of the fair market value of one share of Class A Common Stock on (i) the date the SARs are exercised, and (ii) $1.44, the Issuer's closing price on July 1, 2024 (the date the SARs were granted, the "Grant Date").

F2 · derivative.exercise_date: These Stock Appreciation Rights ("SARs") were granted to the Reporting Person on July 1, 2024 under the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and vest (i) 25% upon the Issuer first achieving trailing twelve month Adjusted EBITDA ("TTM Adjusted EBITDA") of $50.0 million after the date of grant, (ii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $60.0 million after the date of grant, (iii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $70.0 million after the date of grant and (iv) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $80.0 million after the date of grant, in each case, subject to the terms of the Plan and an award agreement entered into between the Reporting Person and the Issuer pursuant to the Plan.

SEC source: 0001628280-24-031213 · wk-form4_1720055144.xml · derivative · entry 1

Kidambi Tridivesh · CIK 0001906862 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 700,000

Underlying: Class A Common Stock · 700,000 shares

Expires 2031-07-01

F1 · security: These stock appreciation rights (these "SARs") were granted to the Reporting Person pursuant to the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and a corresponding Stock Appreciation Rights Grant Notice and Award Agreement between System1, Inc. (the "Issuer") and the Reporting Person. The SARs reported on this Form 4 represent the right to receive (at the Issuer's discretion), upon exercise of the SARs by the Reporting Person, a payment in either (x) Class A Common Stock, par value $0.0001 per share ("Class A Common Stock") or (y) cash, in the amount equal to the number of shares of Class A Common Stock underlying the number of SARs being exercised multiplied by the excess of the fair market value of one share of Class A Common Stock on (i) the date the SARs are exercised, and (ii) $1.44, the Issuer's closing price on July 1, 2024 (the date the SARs were granted, the "Grant Date").

F2 · derivative.exercise_date: These Stock Appreciation Rights ("SARs") were granted to the Reporting Person on July 1, 2024 under the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and vest (i) 25% upon the Issuer first achieving trailing twelve month Adjusted EBITDA ("TTM Adjusted EBITDA") of $50.0 million after the date of grant, (ii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $60.0 million after the date of grant, (iii) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $70.0 million after the date of grant and (iv) 25% upon the Issuer first achieving TTM Adjusted EBITDA of $80.0 million after the date of grant, in each case, subject to the terms of the Plan and an award agreement entered into between the Reporting Person and the Issuer pursuant to the Plan.

SEC source: 0001628280-24-031212 · wk-form4_1720055103.xml · derivative · entry 1

Weinrot Daniel J · CIK 0001624457 · General Counsel & Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 525,000

Underlying: Class A Common Stock · 525,000 shares

Expires 2031-07-01

F1 · security: These stock appreciation rights (the "SARs") were granted to the Reporting Person pursuant to the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and a corresponding Stock Appreciation Rights Grant Notice and Award Agreement between System1, Inc. (the "Issuer") and the Reporting Person. The SARs reported on this Form 4 represent the right to receive (at the Issuer's discretion), upon exercise of the SARs by the Reporting Person, a payment in either (x) Class A Common Stock, par value $0.0001 per share ("Class A Common Stock") or (y) cash, in the amount equal to the number of shares of Class A Common Stock underlying the number of SARs being exercised multiplied by the excess of the fair market value of one share of Class A Common Stock on (i) the date the SARs are exercised, and (ii) $1.44, the Issuer's closing price on July 1, 2024 (the date the SARs were granted, the "Grant Date").

F2 · derivative.exercise_date: These Stock Appreciation Rights (the "SARs") were granted to the Reporting Person on July 1, 2024 under the System1, Inc. 2024 Stock Appreciation Rights Plan, as amended (the "Plan") and vest (i) 25% (or 131,250 SARs) upon the Issuer first achieving trailing twelve month Adjusted EBITDA ("TTM Adjusted EBITDA") of $50.0 million after the date of grant, (ii) 25% (or 131,250 SARs) upon the Issuer first achieving TTM Adjusted EBITDA of $60.0 million after the date of grant, (iii) 25% (or 131,250 SARs) upon the Issuer first achieving TTM Adjusted EBITDA of $70.0 million after the date of grant and (iv) 25% (or 131,250 SARs) upon the Issuer first achieving TTM Adjusted EBITDA of $80.0 million after the date of grant, in each case, subject to the terms of the Plan and an award agreement entered into between the Reporting Person and the Issuer pursuant to the Plan.

SEC source: 0002012590-24-000012 · wk-form4_1719964677.xml · nonDerivative · entry 1

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,361,546

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F2 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.44 to $1.45, 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.

SEC source: 0002012590-24-000010 · wk-form4_1719534448.xml · nonDerivative · entry 3

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,338,410

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F3 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.37 to $1.42, 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.

SEC source: 0002012590-24-000010 · wk-form4_1719534448.xml · nonDerivative · entry 2

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,288,256

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F2 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.42 to $1.45, 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.

SEC source: 0002012590-24-000010 · wk-form4_1719534448.xml · nonDerivative · entry 1

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,244,949

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F2 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.42 to $1.45, 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.

SEC source: 0002012590-24-000008 · wk-form4_1719277125.xml · nonDerivative · entry 3

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,226,644

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

SEC source: 0002012590-24-000008 · wk-form4_1719277125.xml · nonDerivative · entry 2

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,225,444

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

F2 · price: The price reported in Column 4 is a weighted average price. The shares were purchased in more than one transaction at prices ranging from $1.43 to $1.45, 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.

SEC source: 0002012590-24-000008 · wk-form4_1719277125.xml · nonDerivative · entry 1

CEE Holdings Trust · CIK 0002012590 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,221,013

F1 · shares: The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the reporting person.

SEC source: 0001504477-24-000003 · wk-form4_1719018033.xml · nonDerivative · entry 1

Blend L Michael · CIK 0001504477 · Director · CEO & Chairman

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F1 · kind: Mr. Blend sold 725,000 shares to CEE Holdings Trust, a trust established for the benefit of Mr. Charles Ursini, the Company's Co-Founder, President & Chief Operating Officer, and a member of the Board of Directors, in a privately negotiated arm's length transaction that was not conducted through the exchange on which the Issuer's publicly traded securities are listed.

F1 · price: Mr. Blend sold 725,000 shares to CEE Holdings Trust, a trust established for the benefit of Mr. Charles Ursini, the Company's Co-Founder, President & Chief Operating Officer, and a member of the Board of Directors, in a privately negotiated arm's length transaction that was not conducted through the exchange on which the Issuer's publicly traded securities are listed.

SEC source: 0001909643-24-000008 · wk-form4_1719017992.xml · nonDerivative · entry 1

Lone Star Friends Trust · CIK 0001909643 · 10% owner

Blend Stanley · CIK 0001912571 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust (Lone Star Friends Trust)

Disclosed balance after: 956,423

F1 · kind: Lone Star Friends Trust, a trust established for the benefit of Mr. Michael Blend, the Company's Co-Founder, CEO and Chairman of the Board, sold 4,775,000 shares to CEE Holdings Trust, a trust established for the benefit of Mr. Charles Ursini, the Company's Co-Founder, President & Chief Operating Officer, and a member of the Board of Directors, in a privately negotiated arm's length transaction that was not conducted through the exchange on which the Issuer's publicly traded securities are listed.

F2 · price: In connection with the sale reported on this Form 4, the Reporting Person disgorged $930.00 to the Company with respect to 11,613 shares purchased by the Reporting Person in March 2024 pursuant to a 10b5-1 trading plan previously entered into by the Reporting Person.

F3 · ownership.direct: Mr. Stanley Blend is the Trustee of Lone Star Friends Trust.

SEC source: 0001909643-24-000011 · wk-form4a_1719451836.xml · nonDerivative · entry 1

Lone Star Friends Trust · CIK 0001909643 · 10% owner

Blend Stanley · CIK 0001912571 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust (Lone Star Friends Trust)

Disclosed balance after: 1,850,215

F1 · kind: Lone Star Friends Trust, a trust established for the benefit of Mr. Michael Blend, the Company's Co-Founder, CEO and Chairman of the Board, sold 4,775,000 shares to CEE Holdings Trust, a trust established for the benefit of Mr. Charles Ursini, the Company's Co-Founder, President & Chief Operating Officer, and a member of the Board of Directors, in a privately negotiated arm's length transaction that was not conducted through the exchange on which the Issuer's publicly traded securities are listed.

F2 · price: In connection with the sale reported on this Form 4, the Reporting Person disgorged $930.00 to the Company with respect to 11,613 shares purchased by the Reporting Person in March 2024 pursuant to a 10b5-1 trading plan previously entered into by the Reporting Person.

F3 · ownership.direct: Mr. Stanley Blend is the Trustee of Lone Star Friends Trust.

SEC source: 0001628280-24-028153 · wk-form4_1718323235.xml · nonDerivative · entry 1

Civantos John · CIK 0001915482 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 306,134

F1 · shares: Represents a grant of 126,667 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Mr. Civantos' continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Mr. Civantos continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 143,276 unvested RSUs.

SEC source: 0001628280-24-028155 · wk-form4_1718323291.xml · nonDerivative · entry 1

Kumar Tanmay · CIK 0001814526 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 201,967

F1 · shares: Represents a grant of 126,667 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Mr. Kumar's continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Mr. Kumar continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 144,591 unvested RSUs.

SEC source: 0001628280-24-028160 · wk-form4_1718323453.xml · nonDerivative · entry 1

Fowler William Dexter · CIK 0001858473 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 218,433

F1 · shares: Represents a grant of 126,667 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Mr. Fowler's continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Mr. Fowler continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 143,276 unvested RSUs.

SEC source: 0001628280-24-028159 · wk-form4_1718323412.xml · nonDerivative · entry 1

MARTIRE FRANK R · CIK 0001226913 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 265,752

F1 · shares: Represents a grant of 153,333 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Mr. Martire's continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Mr. Martire continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 173,439 unvested RSUs.

SEC source: 0001628280-24-028158 · wk-form4_1718323385.xml · nonDerivative · entry 1

Caswell Ryan R. · CIK 0001840522 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 235,778

F1 · shares: Represents a grant of 120,000 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Mr. Caswell's continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Mr. Caswell continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 135,981 unvested RSUs.

SEC source: 0001628280-24-028157 · wk-form4_1718323347.xml · nonDerivative · entry 1

Naidu Taryn Jogi · CIK 0001519257 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 235,628

F1 · shares: Represents a grant of 140,000 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Mr. Naidu's continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Mr. Naidu continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 168,690 unvested RSUs.

SEC source: 0001628280-24-028156 · wk-form4_1718323318.xml · nonDerivative · entry 1

Kazerani Moujan · CIK 0001845026 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 252,924

F1 · shares: Represents a grant of 146,667 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Ms. Kazerani's continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Ms. Kazerani continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 165,900 unvested RSUs.

SEC source: 0001628280-24-028154 · wk-form4_1718323261.xml · nonDerivative · entry 1

Horn Caroline · CIK 0001907126 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 224,181

F1 · shares: Represents a grant of 130,000 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Ms. Horn's continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Ms. Horn continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 147,046 unvested RSUs.

SEC source: 0001628280-24-028151 · wk-form4_1718323190.xml · nonDerivative · entry 1

Prince Jennifer Mindy · CIK 0001907037 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 222,433

F1 · shares: Represents a grant of 126,667 restricted stock units ("RSUs) which convert into Class A Common Stock on a one-for-one basis, pursuant to the 2022 Incentive Award Plan of the Issuer in connection with Ms. Prince's continued service as a member of its Board of Directors as of the close of business on the date of its annual shareholder meeting. The RSUs vest in four (4) substantially equal quarterly installments on each of September 15, 2024, December 15, 2024, March 15, 2025 and June 15, 2025 as long Ms. Prince continues to serve as a Director of the Issuer through the applicable vesting dates.

F2 · balance_after: Includes 143,276 unvested RSUs.

SEC source: 0001907144-24-000008 · wk-form4_1715905900.xml · nonDerivative · entry 1

Robinson Jennifer Lynn · CIK 0001907144 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 166,814

F1 · shares: Upon the vesting of 7,368 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 2,629 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 48,316 unvested RSUs.

SEC source: 0001907144-24-000006 · wk-form4_1714523586.xml · nonDerivative · entry 1

Robinson Jennifer Lynn · CIK 0001907144 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 169,443

F1 · shares: Upon the vesting of 6,281 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 2,242 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 55,684 unvested RSUs.

SEC source: 0001907093-24-000008 · wk-form4_1714523539.xml · nonDerivative · entry 1

Sestanovich Elizabeth · CIK 0001907093 · Chief People Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 146,455

F1 · shares: Upon the vesting of 3,750 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 1,338 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 29,566 unvested RSUs.

F3 · balance_after: Includes 174 shares received in connection with pro-rata distributions from OpenMail2, LLC to its members, for no consideration and in an exempt transaction under Rule 16a-9, since the Reporting Person's last reportable transaction filed on Form 4.

SEC source: 0001906862-24-000004 · wk-form4_1714523497.xml · nonDerivative · entry 1

Kidambi Tridivesh · CIK 0001906862 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 676,912

F1 · shares: Upon the vesting of 6,250 restricted stock units ("RSUs") previously granted to the reporting person, the Company withheld 2,230 shares to cover the reporting person's tax withholding obligation with respect to the vesting of such RSUs.

F2 · balance_after: Includes 43,750 unvested RSUs.