---
schema_version: "secwatch.filing_event.v1"
accession: "0001437749-23-007171"
form_type: "8-K"
ticker: "KFS"
cik: "0001072627"
company_name: "KINGSWAY FINANCIAL SERVICES INC"
filed_at: "2023-03-20T23:59:59+00:00"
generated_at: "2026-06-17T22:49:43.706335+00:00"
event_type: "debt"
sentiment: "positive"
materiality_score: 0.8
calibrated_materiality_score: 0.8
confidence: "high"
source: SEC EDGAR
---

# Kingsway repurchases $74.6M trust preferred debt and $21M deferred interest; only $0.9M left

## Summary
- Repurchased $74.6M principal and $21M deferred interest at 60.8 cents on dollar for >20% IRR.
- Remaining $0.9M principal and $0.2M deferred interest expected to close in coming days.
- Pro forma total debt post-repurchase: $45.7M (bank loans $34.3M, sub debt $11.4M), down from ~$300M.
- Operating income grew to $13.4M in 2022 vs $4.2M in 2018; adjusted EBITDA from ops increased 36% CAGR to $13.5M.

## SEC filing metadata
- accession: 0001437749-23-007171
- form_type: 8-K
- ticker: KFS
- cik: 0001072627
- company_name: KINGSWAY FINANCIAL SERVICES INC
- filed_at: 2023-03-20T23:59:59+00:00
- event_type: debt
- sentiment: positive
- materiality_score: 0.8
- calibrated_materiality_score: 0.8
- confidence: high
- sec_items: 8.01, 9.01
- EDGAR index: https://www.sec.gov/Archives/edgar/data/1072627/000143774923007171/0001437749-23-007171-index.htm
- EDGAR primary document: https://www.sec.gov/Archives/edgar/data/1072627/000143774923007171/kfs20230317_8k.htm

## Machine-readable alternates
- HTML: https://secwatch.observer/filing/0001437749-23-007171
- JSON: https://secwatch.observer/filing/0001437749-23-007171.json
- Plain text: https://secwatch.observer/filing/0001437749-23-007171.txt

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