System1, Inc. (SST): debt financing — System1 exchanges $302.6M debt for $150M term loan, $39.3M preferred stock, and cash

System1, Inc.

New $150M term loan maturing 2031 replaces existing $252.6M term loan and $50M revolver.
Issues convertible preferred stock with $39.3M aggregate stated value, convertible at $10.40/share, ~27.4% of common equity on as-converted basis.
One-time cash payment of ~$31.4M to lenders; all outstanding disputes settled.
Transaction requires shareholder approval for preferred stock; expected close in Q3 2026.
Management cites debt reduction of over $160M from beginning of 2026 and extended maturity to 2031.

item 1.01 item 2.03 item 3.02 item 7.01 item 9.01

Key facts

Extracted from this filing and checked against the source text.

Debt Financings SEC 8-K Item 2.03/2.04 confidence 0.9

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

Instrument: term loan
Principal: $150.0 million
Counterparty: Participating Lenders
Rate: SOFR + 5.00%
Maturity: January 2031
Event: incurrence

Exact text from the filing

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

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Equity Issuances SEC 8-K Item 3.02/3.03 confidence 0.9

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.

Security: preferred stock
Shares: 39,250 shares of Series A Cumulative Convertible Preferred Stock
Purchaser: Participating Lenders
Consideration: exchange for a portion of the Existing Loans; aggregate initial stated value of $39.3 million

Exact text from the filing

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”)

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Material Agreements SEC 8-K Item 1.01/1.02 confidence 0.9

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).

Action: entry
Agreement: credit facility
Counterparty: Participating Lenders
Value: $150.0 million term loan facility, 39,250 shares of Series A Cumulative Convertible Preferred Stock
Effective: 2026-05-29

Exact text from the filing

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”).

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41 debt financings filed in the last 30 days. Browse all debt financings →

System1, Inc. filing history →

Source: SEC EDGAR

accession 0001805833-26-000030

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