{"schema_version":"secwatch.filing_event.v1","accession":"0001880613-25-000123","form_type":"8-K","ticker":"DRCT","cik":"0001880613","company_name":"Direct Digital Holdings, Inc.","filed_at":"2025-10-20T23:59:59+00:00","discovered_at":"2026-05-14T18:02:40.969566+00:00","generated_at":"2026-05-17T03:18:06.086481+00:00","sec_items":["1.01","2.03","3.02","3.03","5.03","9.01"],"event_type":"debt","sentiment":"negative","materiality_score":0.85,"calibrated_materiality_score":0.85,"confidence":"high","headline":"Direct Digital converts $10M debt to preferred; adds EBITDA loss covenants","bullets":["Converted $10M term loans into 10,000 Series A Preferred shares; total preferred face now $35M.","Paid $3.5M amendment fee added to principal; $9.99M term loans remain outstanding.","New covenants: min cash $0.45M, min quarterly EBITDA loss $(0.652M) and $(1.921M) for Q4 2025 and Q1 2026.","Existing defaults (non-payment, EBITDA miss, cash covenant) waived; must appoint independent director by Oct 29.","Preferred pays 10% cumulative dividend, converts at $2.50/sh, liquidation preference 3x accumulation."],"urls":{"canonical":"https://secwatch.observer/filing/0001880613-25-000123","json":"https://secwatch.observer/filing/0001880613-25-000123.json","markdown":"https://secwatch.observer/filing/0001880613-25-000123.md","text":"https://secwatch.observer/filing/0001880613-25-000123.txt","edgar_index":"https://www.sec.gov/Archives/edgar/data/1880613/000188061325000123/0001880613-25-000123-index.htm","edgar_primary_document":"https://www.sec.gov/Archives/edgar/data/1880613/000188061325000123/drct-20251014.htm"},"model":{"generated_by":"deepseek-v4-flash:cloud@v2","generated_at":"2026-05-17T03:18:06.086481+00:00"},"review":{"review_status":"machine_generated","human_reviewed":false,"corrected":false,"correction_note":null,"correction_timestamp":null,"superseded_by":null,"related_filings":[]},"source_grounded_claims":[{"claim_id":"c9a9bbba6c8e7afe8b745118863f30092858fa7c","claim":"Direct Digital Holdings, Inc. issued $10.0 million face amount of Series A Preferred Stock of preferred stock to Lafayette Square USA, Inc. for conversion and exchange of $10.0 million aggregate principal amount of term loans and other debt obligations.","evidence_excerpt":"the parties agreed to convert and exchange term loans and other debt obligations with an aggregate principal amount of $10.0 million for newly authorized shares of Series A Preferred Stock, par value $0.001, of the Company (the “ Series A Preferred Stock ”), with an aggregate face amount of $10.0 million issued to Lafayette.","evidence_source":"SEC 8-K Item 3.02/3.03","evidence_url":"https://www.sec.gov/Archives/edgar/data/1880613/000188061325000123/0001880613-25-000123-index.htm","confidence":0.9,"family_label":"Equity Issuances","details":[{"label":"Security","value":"preferred stock"},{"label":"Shares","value":"$10.0 million face amount of Series A Preferred Stock"},{"label":"Purchaser","value":"Lafayette Square USA, Inc."},{"label":"Consideration","value":"conversion and exchange of $10.0 million aggregate principal amount of term loans and other debt obligations"}],"fact_type":"equity_issuance"},{"claim_id":"7b306e1f68865b799f79e6c02134b036dc53e25d","claim":"Direct Digital Holdings, Inc.: Amended and restated Certificate of Designation of Series A Convertible Preferred Stock, increasing designated shares from 25,000 to 35,000 and modifying dividend and voting terms (effective 2025-10-15).","evidence_excerpt":"Pursuant to the terms of the Ninth Amendment, on October 15, 2025, the Company filed the Amended and Restated Certificate of Designation of Series A Convertible Preferred Stock (the “ A&R Certificate of Designation ”) with the Secretary of State of the State of Delaware, which amended and restated in its entirety the Certificate of Designation establishing the Series A Convertible Preferred Stock, filed on August 8, 2025.","evidence_source":"SEC 8-K Item 5.03/5.05/5.06","evidence_url":"https://www.sec.gov/Archives/edgar/data/1880613/000188061325000123/0001880613-25-000123-index.htm","confidence":0.9,"family_label":"Governance Changes","details":[{"label":"Change","value":"charter amendment"},{"label":"Effective","value":"2025-10-15"}],"fact_type":"governance_change"}],"license":"Source filings: public domain (SEC EDGAR). Summaries (headline + bullets): CC-BY-4.0; attribute https://secwatch.observer"}