---
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"
generated_at: "2026-05-21T01:07:42.936431+00:00"
event_type: "debt"
sentiment: "neutral"
materiality_score: 0.45
calibrated_materiality_score: 0.45
confidence: "high"
source: SEC EDGAR
---

# Kingsway issues $2M of 8% Class D Preferred Stock convertible into common

## Summary
- 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.

## SEC filing metadata
- 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
- event_type: debt
- sentiment: neutral
- materiality_score: 0.45
- calibrated_materiality_score: 0.45
- confidence: high
- sec_items: 1.01, 2.03, 3.02, 5.03, 9.01
- 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

## Machine-readable alternates
- HTML: https://secwatch.observer/filing/0001437749-25-017518
- JSON: https://secwatch.observer/filing/0001437749-25-017518.json
- Plain text: https://secwatch.observer/filing/0001437749-25-017518.txt

## Key facts
- Governance Changes
  KINGSWAY FINANCIAL SERVICES INC: Filed Certificate of Designations establishing Class D Preferred Stock (effective 2025-05-07).
  - Change: charter amendment
  - Effective: 2025-05-07
  source text: On May 7, 2025, the Company filed the Class D Certificate of Designations with the Secretary of State of the State of Delaware.
  evidence_url: https://www.sec.gov/Archives/edgar/data/1072627/000143774925017518/0001437749-25-017518-index.htm

This AI-assisted summary is a reading aid. Review the linked SEC EDGAR filing before relying on any specific claim.