---
schema_version: "secwatch.filing_event.v1"
accession: "0001213900-23-016271"
form_type: "8-K"
ticker: "KFS"
cik: "0001072627"
company_name: "KINGSWAY FINANCIAL SERVICES INC"
filed_at: "2023-03-01T23:59:59+00:00"
generated_at: "2026-06-18T16:57:16.392672+00:00"
event_type: "other_material"
sentiment: "neutral"
materiality_score: 0.6
calibrated_materiality_score: 0.6
confidence: "high"
source: SEC EDGAR
---

# Kingsway to redeem all Class A Preferred Stock for ~$6.1M; enters $10M delayed draw term loan

## Summary
- Subsidiaries entered Second Amendment to Loan Agreement with CIBC Bank USA for $10M delayed draw term loan, maturing Dec 1, 2025.
- Loan requires quarterly principal payments of 3.75% of drawn amount; commitment fee $25K, draw fee 75 bps.
- Senior Cash Flow Leverage Ratio maximum increased for certain periods under the amendment.
- Company plans to redeem all outstanding Class A Preferred Stock on March 15, 2023 at $25/share plus accrued dividends, estimated $6.1M aggregate using cash on hand.

## SEC filing metadata
- accession: 0001213900-23-016271
- form_type: 8-K
- ticker: KFS
- cik: 0001072627
- company_name: KINGSWAY FINANCIAL SERVICES INC
- filed_at: 2023-03-01T23:59:59+00:00
- event_type: other_material
- sentiment: neutral
- materiality_score: 0.6
- calibrated_materiality_score: 0.6
- confidence: high
- sec_items: 1.01, 2.03, 8.01
- EDGAR index: https://www.sec.gov/Archives/edgar/data/1072627/000121390023016271/0001213900-23-016271-index.htm
- EDGAR primary document: https://www.sec.gov/Archives/edgar/data/1072627/000121390023016271/ea174515-8k_kingsway.htm

## Machine-readable alternates
- HTML: https://secwatch.observer/filing/0001213900-23-016271
- JSON: https://secwatch.observer/filing/0001213900-23-016271.json
- Plain text: https://secwatch.observer/filing/0001213900-23-016271.txt

## Key facts
- Debt Financings
  KINGSWAY FINANCIAL SERVICES INC amended credit facility with CIBC Bank USA.
  - Instrument: credit facility
  - Counterparty: CIBC Bank USA
  - Event: amendment
  source text: The Amendment also modifies the Senior Cash Flow Leverage Ratio (as such term is defined in the Amendment) to increase the maximum permissible Senior Cash Flow Leverage Ratio of the Loan Parties for certain periods.
  evidence_url: https://www.sec.gov/Archives/edgar/data/1072627/000121390023016271/0001213900-23-016271-index.htm
- Debt Financings
  KINGSWAY FINANCIAL SERVICES INC incurred term loan of up to Ten Million Dollars ($10,000,000) with CIBC Bank USA maturing December 1, 2025.
  - Instrument: term loan
  - Principal: up to Ten Million Dollars ($10,000,000)
  - Counterparty: CIBC Bank USA
  - Maturity: December 1, 2025
  - Event: incurrence
  source text: The Amendment provides for an additional delayed draw term loan in the principal amount of up to Ten Million Dollars ($10,000,000) (the “DDTL”), with a maturity date of December 1, 2025.
  evidence_url: https://www.sec.gov/Archives/edgar/data/1072627/000121390023016271/0001213900-23-016271-index.htm
- Material Agreements
  KINGSWAY FINANCIAL SERVICES INC amended Second Amendment to Loan and Security Agreement with CIBC Bank USA valued at Ten Million Dollars ($10,000,000) (effective 2023-02-28).
  - Action: amendment
  - Agreement: credit facility
  - Counterparty: CIBC Bank USA
  - Value: Ten Million Dollars ($10,000,000)
  - Effective: 2023-02-28
  source text: On February 28, 2023, certain subsidiaries (such subsidiaries, collectively the “Loan Parties”) of Kingsway Financial Services, Inc. (the “Company”) entered into the Second Amendment to Loan and Security Agreement (the “Amendment”) with CIBC Bank USA as lender (“Lender”). The Amendment provides for an additional delayed draw term loan in the principal amount of up to Ten Million Dollars ($10,000,000) (the “DDTL”), with a maturity date of December 1, 2025.
  evidence_url: https://www.sec.gov/Archives/edgar/data/1072627/000121390023016271/0001213900-23-016271-index.htm

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