{"schema_version":"secwatch.filing_event.v1","accession":"0001437749-25-017518","form_type":"8-K","ticker":"KFS","cik":"0001072627","company_name":"KINGSWAY FINANCIAL SERVICES INC","filed_at":"2025-05-19T23:59:59+00:00","discovered_at":"2026-05-14T18:02:47.427599+00:00","generated_at":"2026-05-21T01:07:42.936431+00:00","sec_items":["1.01","2.03","3.02","5.03","9.01"],"event_type":"debt","sentiment":"neutral","materiality_score":0.45,"calibrated_materiality_score":0.45,"confidence":"high","headline":"Kingsway issues $2M of 8% Class D Preferred Stock convertible into common","bullets":["Sold 80,000 shares of Class D Preferred Stock at $25/share for $2.0M aggregate proceeds.","Dividend rate 8% per annum, rising to 18% if unpaid for two consecutive quarters.","Each preferred share convertible into 2.6316 common shares (max 210,526 shares) through May 2032.","Mandatory redemption on May 7, 2032 at $25/share plus accrued dividends.","Optional redemption of up to 25% after certain asset sales yielding 15% IRR."],"urls":{"canonical":"https://secwatch.observer/filing/0001437749-25-017518","json":"https://secwatch.observer/filing/0001437749-25-017518.json","markdown":"https://secwatch.observer/filing/0001437749-25-017518.md","text":"https://secwatch.observer/filing/0001437749-25-017518.txt","edgar_index":"https://www.sec.gov/Archives/edgar/data/1072627/000143774925017518/0001437749-25-017518-index.htm","edgar_primary_document":"https://www.sec.gov/Archives/edgar/data/1072627/000143774925017518/kfs20250519_8k.htm"},"model":{"generated_by":"deepseek-v4-flash:cloud@v2","generated_at":"2026-05-21T01:07:42.936431+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":"2c11c65b948341a024be96dc8cee99038afa9bb6","claim":"KINGSWAY FINANCIAL SERVICES INC: Filed Certificate of Designations establishing Class D Preferred Stock (effective 2025-05-07).","evidence_excerpt":"On May 7, 2025, the Company filed the Class D Certificate of Designations with the Secretary of State of the State of Delaware.","evidence_source":"SEC 8-K Item 5.03/5.05/5.06","evidence_url":"https://www.sec.gov/Archives/edgar/data/1072627/000143774925017518/0001437749-25-017518-index.htm","confidence":0.9,"family_label":"Governance Changes","details":[{"label":"Change","value":"charter amendment"},{"label":"Effective","value":"2025-05-07"}],"fact_type":"governance_change"}],"license":"Source filings: public domain (SEC EDGAR). Summaries (headline + bullets): CC-BY-4.0; attribute https://secwatch.observer"}