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Stock Ratings / Financials / KWY / options
KINS (72) NODK (31) GBLI (43) OSG (33) ⌘ Pro Terminal β†’

Kingsway Corporation (KWY) Options Positioning, Max Pain & Unusual Sweeps

$9.96 +1.32% NYSE β€’ Live Quote vs Prior Daily Close (Synced Snapshot) EXT / AFTER-HRS: $9.96

Kingsway Corporation (KWY) carries a Roarable Rating of E (Strong Sell) with 32/100 RQD Confidence due to weak cash-flow efficiency and sensitivity to current interest rates. Wait for business cash flow and institutional buying to improve before committing fresh capital.

ROARABLE E β€’ RED ALERT Cap $288.2M
πŸ“€ Share Live RQD Speedometer Card: 𝕏 Post Reddit StockTwits ⬇ Live SVG Card
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πŸ€– Mara Quenwick β€’ AI Quant Lead (Click for Instant Brief) Is KWY stock a Buy, Hold, or Sell right now according to Roarable's RQD model?
β–Ό

As of 2026-11-03, Kingsway Corporation (NYSE: KWY) is rated E (Strong Sell / SELL) by Roarable's 5-pillar RQD engine with a composite confidence score of 32/100 at a spot price of $9.96 (+1.32% 1D, market cap $288.2M). Pillar breakdown: Fundamental Cash Engine 3/20, Institutional 13F & Options Flow 8/20, SEC Balance-Sheet Forensics 10/20, FRED Macro Regime Fit 6/20, and Executive Insider Alignment 5/20. Across 1097 tracked Financials issuers, KWY ranks #1003 in composite RQD confidence.

βœ“ Pre-computed one-to-many AI Quant brief
πŸ€– Ellis Vennor β€’ AI Peer & Flow Quant (Click for Instant Brief) How does KWY compare to KINS and NODK in the Financials sector?
β–Ό

Within the Financials sector (Property-Casualty Insurers), KWY carries a Roarable E (32/100 RQD), trailing P/E of N/A, gross margin of β€”, and ROIC of -13.6%. By comparison, KINS (Kingstone Companies Inc.) holds a B grade (72/100 RQD, P/E 7.1x, ROIC 33.2%, cap $295.5M) and NODK (NI Holdings Inc.) posts a E grade (31/100 RQD, P/E N/A, ROIC -4.3%, cap $308.7M). Among the 5-stock peer group, KINS leads on earnings multiple (7.1x) while KINS leads on capital efficiency (33.2% ROIC).

βœ“ Pre-computed one-to-many AI Quant brief
πŸ€– Gideon Ashmere β€’ AI SEC 10-K Forensics (Click for Instant Brief) What are the biggest fundamental strengths and SEC risk factors for KWY?
β–Ό

Per KWY's SEC EDGAR XBRL 10-K filing (FY2025, filed 2025-12-31, CIK 0001072627), Kingsway Corporation generated $135.0M in revenue (+23.4% YoY), -$10.3K in net income, and -$3.0K in free cash flow against $231.5M in total assets and $0 in total debt. Key quantitative strengths: Established market leader in Financials with deep daily trading liquidity. Primary risk factors monitored: Company executives have done more routine share selling than personal cash buying lately. Institutional options positioning shows a 50% call / 50% put premium split.

βœ“ Pre-computed one-to-many AI Quant brief
πŸ€– AI Quant Disclosure: Roarable Analysts are proprietary AI Quant Specialists β€” not human financial advisors. Pre-computed one-to-many briefings above are free; interactive 1-on-1 Q&A, custom AI sifting/indicator alerts, and personal ChatGPT/Claude MCP connections require a $9.95/mo Pro account (currently waitlist-only).
INTERACTIVE SCENARIO DECK:
πŸ›‘οΈ Portfolio Crash X-Ray
EXT / AFTER-HRS: $9.96 (+0.05%)🧬 Dilution Drag (+1.92% YoY Shares)βš™οΈ Cash Engine: 3/20 (E) β€’ 0% FCF Margin
Verify 90D Bucket Audit β†’
πŸ“Š Historical Track Record Warning: Scores below 50 (32/100 Β· E) historically underperformed SPY in 71% of rolling 90-day windows (-9.2% avg 90D alpha vs SPY β€’ 29.0% hit rate).
Audit Bucket Track Record β†’
RQD QUANT TACHOMETERRED ALERT β€’ E
025507510032
3-of-3 Quant Analysts Bearish Warning
Cash
SEC
Whale

Impersonal quantitative research (0–100 RQD rubric) β€” not individualized investment advice. Past performance does not guarantee future results. Full Disclaimer

5-PILLAR RQD RADARRw E Β· Rk D-
Cash (3)Whales (8)SEC (10)Macro (6)CEO (5)
Each axis scored 0–20
12M PRICE TARGET CONE-11.7% Base Target
$16 Bull$9 Base$7 Bear
πŸ“¬ FREE KWY RATING-CHANGE & BRIEFING ALERTSManage / Unsubscribe
WHALE OPTIONS SNAPSHOT: β€” (No Active Options Snapshot on file for KWY)Realized 20D OHLCV Swing Band: Β±6.4%
Deterministic 5-Pillar Attribution (32/100 Composite)
πŸ” WHY KWY SCORES 32/100 (E) β€” TOP 3 DRIVERS2 Bullish Pillars + #1 Risk Drag
β–² #1 Bullish Driver: SEC 10-K Forensic Risk+10/20 pts (31% of score)

Altman Z-Score 3.80 (FORTRESS SAFE (>3.0)) β€’ Piotroski F-Score 2/9

β–² #2 Bullish Driver: Whale & Options Positioning+8/20 pts (25% of score)

20D Institutional Volume Accumulation (Β±6.4% realized swing band)

β–Ό #1 Drag / Risk Factor: Cash Engine Quality4/20 pts (-16 pt drag)

Capital intensity & 0% operating margin leave 16 pts on the table

πŸ“ˆ PAST 4 QUARTERS RQD vs SUBSEQUENT RETURNQ1 β†’ Q2 β†’ Q3 β†’ Current
Q1 (-3Q)
24
Grade E$9.48+1.5% Next Q
Q2 (-2Q)
27
Grade E$9.62+0.4% Next Q
Q3 (-1Q)
29
Grade E$9.66+3.1% Next Q
Current
32
Grade E$9.96-9.2% Hist 90D Ξ±
Trajectory: E (24) β†’ E (32)Full Audit β†’
βš”οΈ ADVERSARIAL OPPOSING CASE & FORENSIC KILL-SWITCH (WHY THE BULL/BEAR THESIS COULD FAIL)CONTRARIAN TURNAROUND & SHORT-SQUEEZE DOSSIER

βš”οΈ Adversarial Opposing Case: What Could Spark a KWY Turnaround Squeeze

Gideon Ashmere Forensic Desk β†’

While KWY currently carries a cautious 32/100 (E) rating due to Cash Engine Quality (4/20), shorts face asymmetric squeeze risk if free cash flow inflects or management executes accretive buybacks.

πŸš€ Contrarian Squeeze Trigger #1

Established market leader in Financials with deep daily trading liquidity.

πŸš€ Contrarian Squeeze Trigger #2

Options & Short-Covering Gamma: Reclaiming the 50-day SMA ($9.67) and Max Pain ($10.46) forces dealer call-delta covering toward $15.69.

πŸš€ Contrarian Squeeze Trigger #3

Forensic Repair Trigger: Halting share dilution (Dilution Drag (+1.92% YoY Shares)) or retiring high-cost debt immediately upgrades the SEC 10-K Forensic pillar.

🎲 LIVE PREDICTION MARKET ODDS TIED TO $KWYβ€’ $2.4M Crowd Pool β€’ Kalshi / Polymarket Composite
Contract: β€œKWY Beats Next Quarter EPS Consensus (Dec 30, 2026) & Holds Above 200D SMA”
YES 32%NO 68%Trade / Inspect Odds β†’
CALL VS. PUT WHALE SHARE
β€” (No Active Options Snapshot)
Put/Call Ratio: β€” (No Active Options Snapshot)
MAX-PAIN EXPIRATION MAGNET
β€” (No Active Options Snapshot)
No active options chain max-pain snapshot on file
HISTORICAL 20D VOLATILITY SWING
Β±6.4%
Derived from 20D OHLCV bars (No Active Options Snapshot)

Active Strike Call vs. Put Concentration Ladder (KWY)

β€” (No Active Options Snapshot) β€” No unusual CBOE strike concentration anomalies recorded in the current database snapshot for KWY.

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FTC Disclosure: Roarable may receive partner referral compensation at no cost to you. Partner relationships never influence RQD scores.

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Red-Light Warning Desk: Spotting SEC Cash-Flow & Dilution Risks Before Downgrades (Featuring KWY)

  • βœ“Walkthrough of KWY's RQD Radar, SEC cash-conversion gap & downside invalidation levels
  • βœ“3 asymmetric Bear/Hedge frameworks when 10-year Treasury yields stay elevated
  • βœ“Includes nightly RQD rating-change & forensic signal email alerts on your tracked stocks
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KWY // CANDLESTICK & AUTO-TRENDLINE WORKSTATION6M: -5.59%⚑ TESTING RESISTANCE
2026-11-04O $9.83H $9.96L $9.83C $9.96VOL 34.3K
RES: $10.02SUP: $9.30SMA50: $9.67SMA200: $10.58
$13.39$12.04$10.69$9.34$7.99RES $10.02SUP $9.30$9.962026-05-052026-06-182026-08-052026-09-212026-11-04
PRIMARY-SOURCE FORENSICS, SECOND-ORDER LINKS & AI ANALYST DESK

KWY Dilution Monitor, Expectations Hurdle, Butterfly Connections & Policy Exposure

πŸ¦‹ KWY Butterfly Map β†’ + Track KWY β†’
Share Count & Dilution Monitor

Multi-year comparable XBRL diluted share count not disclosed (ETF or recent listing).

Reverse-DCF Expectations Hurdle
8.0%/yr Implied 5Y Growth

vs. +23.4% actual YoY revenue growth (assuming 9.25% cost of equity & 16.5x terminal multiple).

Ellis Vennor Setup Ledger

No active Ellis Vennor swing setup published on KWY today. View full Setup Ledger β†’

πŸ¦‹ Documented & Second-Order Butterfly Connections Open Graph β†’

No direct multi-tier Butterfly edges indexed yet for KWY. Explore sector supply chains on /butterfly.

AI Analyst Theses, Washington Policy & Company Video
🎬 No recent verified company-specific video clip queued for KWY today (we never pad ticker pages with unrelated generic clips). Browse Macro Video Desk β†’
DETERMINISTIC MULTI-FACTOR EQUITY AUDIT β€’ SEC EDGAR XBRL Γ— RQD PEER BENCHMARK

πŸ“Š Quantitative Sector Peer Comparison, SEC Filing Delta & Investment FAQ (KWY)

Financials Rank #1003 of 1097 βš”οΈ KINS vs KWY Full Matrix β†’

1. Head-to-Head Financials Peer Comparison (KWY vs. KINS, NODK, GBLI, OSG)

Industry: Property-Casualty Insurers (68 Tracked Issuers)

Across 1097 tracked Financials securities in the Roarable RQD universe, Kingsway Corporation (KWY) ranks #1003 by composite RQD confidence (32/100, grade E) and #817 by equity capitalization ($288.2M). Within this direct 5-issuer industry benchmark cohort, KINS leads on earnings valuation at 7.1x trailing P/E, while KINS leads on capital efficiency and profitability with 33.2% ROIC and β€” gross margin. KINS currently holds the highest overall quantitative score in the immediate peer group at 72/100 (B) compared with KWY at 32/100 (E).

Ticker / Company Roarable Grade RQD Score Trailing P/E Gross Margin ROIC 1D Change Market Cap Head-to-Head
KWY ACTIVE
Kingsway Corporation
E 32/100 β€” β€” -13.6% +1.32% $288.2M Benchmark Subject
KINS
Kingstone Companies Inc.
B 72/100 7.1x β€” 33.2% +1.19% $295.5M /kins-vs-kwy β†’
NODK
NI Holdings Inc.
E 31/100 β€” β€” -4.3% +1.14% $308.7M /nodk-vs-kwy β†’
GBLI
Global Indemnity Group LLC (Class A)
D- 43/100 14.2x β€” 3.6% -2.98% $347.7M /gbli-vs-kwy β†’
OSG
Octave Specialty Group Inc.
E 33/100 β€” β€” -35.0% +3.18% $234.3M /osg-vs-kwy β†’

2. Multi-Year SEC XBRL Revenue, Cash Flow & Balance-Sheet Trajectory (FY2023–FY2025)

SEC EDGAR 10-K β€’ FILED 2025-12-31 β€’ CIK 0001072627 β†—

In its most recent audited fiscal period (FY2025, filed 2025-12-31), Kingsway Corporation (KWY) reported GAAP revenue of $135.0M (+23.4% vs. FY2024 revenue of $109.4M , and +30.8% cumulative change since FY2023) , GAAP net income of -$10.3K, operating cash flow of -$3.0K, and free cash flow of -$3.0K (-100.3% YoY). On the balance sheet, KWY closed FY2025 with $231.5M in total assets against $0 in total debt (Altman Z-Score: N/A, Piotroski F-Score: 2/9).

Fiscal Period Filing Date Revenue Net Income Operating Cash Flow Free Cash Flow Total Assets Total Debt
FY2025 (FY) 2025-12-31 $135.0M -$10.3K -$3.0K -$3.0K $231.5M β€”
FY2024 (FY) 2024-12-31 $109.4M -$8.3K $1.1M $1.1M $186.6M β€”
FY2023 (FY) 2023-12-31 $103.2M $24.0K -$26.2M -$26.2M β€” β€”

3. KWY Data-Verified Investor FAQ (RQD Rating, Sector Peers, SEC Forensics & Technicals)

βœ“ SCHEMA.ORG FAQPAGE JSON-LD ENABLED

Is KWY stock a Buy, Hold, or Sell right now according to Roarable's RQD model?

As of 2026-11-03, Kingsway Corporation (NYSE: KWY) is rated E (Strong Sell / SELL) by Roarable's 5-pillar RQD engine with a composite confidence score of 32/100 at a spot price of $9.96 (+1.32% 1D, market cap $288.2M). Pillar breakdown: Fundamental Cash Engine 3/20, Institutional 13F & Options Flow 8/20, SEC Balance-Sheet Forensics 10/20, FRED Macro Regime Fit 6/20, and Executive Insider Alignment 5/20. Across 1097 tracked Financials issuers, KWY ranks #1003 in composite RQD confidence.

How does KWY compare to KINS and NODK in the Financials sector?

Within the Financials sector (Property-Casualty Insurers), KWY carries a Roarable E (32/100 RQD), trailing P/E of N/A, gross margin of β€”, and ROIC of -13.6%. By comparison, KINS (Kingstone Companies Inc.) holds a B grade (72/100 RQD, P/E 7.1x, ROIC 33.2%, cap $295.5M) and NODK (NI Holdings Inc.) posts a E grade (31/100 RQD, P/E N/A, ROIC -4.3%, cap $308.7M). Among the 5-stock peer group, KINS leads on earnings multiple (7.1x) while KINS leads on capital efficiency (33.2% ROIC).

What are the biggest fundamental strengths and SEC risk factors for KWY?

Per KWY's SEC EDGAR XBRL 10-K filing (FY2025, filed 2025-12-31, CIK 0001072627), Kingsway Corporation generated $135.0M in revenue (+23.4% YoY), -$10.3K in net income, and -$3.0K in free cash flow against $231.5M in total assets and $0 in total debt. Key quantitative strengths: Established market leader in Financials with deep daily trading liquidity. Primary risk factors monitored: Company executives have done more routine share selling than personal cash buying lately. Institutional options positioning shows a 50% call / 50% put premium split.

Where is KWY trading relative to its 50-day, 200-day, and 52-week technical levels?

KWY last traded at $9.96 (+1.32% on volume of 34,312 shares), positioning the stock +3.00% above its 50-day simple moving average ($9.67) and -5.86% below its 200-day simple moving average ($10.58). Across its 52-week range of $8.41 to $14.94, KWY sits at the 23.7% percentile with a 14-day RSI of 57.6 (BULLISH MOMENTUM) and an implied next-earnings move of Β±6.4% ($9.32 to $10.60).

Direct Sub-Reports: KWY RQD Cockpit KWY 12M Forecast KWY Earnings & Move KWY Dividends & DRIP KWY Insiders & 13F KWY Whale Options KWY Profit Sankey KWY News & Why
ROARABLE RATING BRIEF β€’ RQD 32/100 (E) βœ“ SEC XBRL & RQD VERIFIED

KWY β€” Kingsway Corporation: What the Facts Mean to a Prospective Investor

Methodology: RQD v6.2 Deterministic 5-Pillar & SEC XBRL Audit
Updated: 2025-12-31

1. Roarable Rating Brief: What This Means to a Prospective Investor

Kingsway Corporation (KWY) earns a live Roarable RQD composite score of 32/100, corresponding to a E letter grade (Roarable Strong Sell) at a spot price of $9.96 (+1.32% 1D, market capitalization $288.2M).

  • Fundamental Cash Engine (3/20): Anchored by return on invested capital (ROIC) of -13.6%, gross margin of β€”, operating margin of -1.8%, and free cash flow yield of 0.00%.
  • Whale 13F & Options Flow (8/20) + Insider Conviction (5/20): Tracks institutional 13F accumulation, CBOE options call/put positioning, and SEC Form 4 / Congressional PTR filings.
  • Macro Regime Fit (6/20) + Forensic Balance Sheet (10/20): Incorporates a 1.00x equity beta, Altman Z-Score of N/A, Piotroski F-Score of 2/9, and Debt/Equity of N/A.

2. Business Model, Unit Margins & SEC Financial Trajectory

Kingsway Corporation (KWY) is a NYSE-listed issuer classified in the Financials sector and Property-Casualty Insurers industry. The profile states the company has a market capitalization of $0.3B.

In its latest audited SEC EDGAR 10-K filing for FY2025 (filed 2025-12-31), Kingsway Corporation (KWY) reported $135.0M in annual revenue (up from $109.4M in FY2024, +23.4% YoY) and -$10.3K in GAAP net income. Over the multi-year SEC filing window from FY2023 ($103.2M revenue, $24.0K net income) through FY2025, KWY scaled operating cash flow to -$3.0K and free cash flow to -$3.0K, backed by $231.5M in total assets against $0 in total debt.

3. Institutional Bull vs. Bear Thesis & Valuation Tradeoff

  • πŸ‚ Primary Bull Case (E β€’ RQD 32/100): Established market leader in Financials with deep daily trading liquidity. Free cash flow yield of 0.00% and institutional whale pillar of 8/20. With Fundamental Cash Engine at 3/20 and Institutional Whale Flow at 8/20, sustained execution supports upside toward the upper end of the $8.41 – $14.94 52-week range.
  • 🐻 Primary Bear Case & Valuation Risk: Company executives have done more routine share selling than personal cash buying lately. Investors must weigh current valuation against -1.8% operating margins and a 1.00x macro beta.

4. 2nd-Order Butterfly Ripples & Key Questions to Watch

The source data therefore does not establish any upstream or downstream dependencies, sector correlations, or 2nd-order bottlenecks for KWY.

  • Key Question #1: Can KWY sustain or expand its -1.8% operating margin and -13.6% ROIC against Property-Casualty Insurers peers over the next 4 quarters?
  • Key Question #2: Following FY2025 revenue of $135.0M and free cash flow of -$3.0K, how will capital allocation balance growth reinvestment against $0 in total debt?
  • Key Question #3: How sensitive is KWY's equity valuation to Financials capital spending cycles and macro interest-rate shifts (Beta 1.00x)?

KWY Live News Feed, Press Releases & Catalyst Wire

Real-time company headlines, analyst actions, and sector developments for Kingsway Corporation (KWY) β€’ Click "Debate This Headline" to argue it in the Roar Pit below

πŸ’¬ Jump to KWY Debate Forum (3) ↓
πŸ”₯ THE ROAR PIT β€’ LIVE COMMUNITY DEBATE 3 Active Posts & Replies

KWY Bull vs. Bear Conversation Board β€” What's Your Call at $9.96?

πŸ‚ 67% BULLISH CONVICTION COMMUNITY TUG-OF-WAR ON KWY 🐻 33% BEARISH CONVICTION
1. Pick Your Side on KWY:
πŸ’‘ Tip: Back up your call with a price target or RQD metric to get upvoted to the top.
BR BreakoutHunter RQD DEBATE OPENER β€’ Swing & Catalyst Trader πŸ‚ BULLISH 🎯 Target: $12.98 (+32.0%)
πŸ“Œ Pinned Debate

Revenue grew from $103.2M in FY 2023 to $135.0M in FY 2025 while the CEO disclosed a share purchase, and a scheduled Q3 2026 results re

Long KWY at $9.83 targeting $12.98. Revenue grew from $103.2M in FY 2023 to $135.0M in FY 2025 while the CEO disclosed a share purchase, and a scheduled Q3 2026 results release on November 5, 2026 is a near-term catalyst.. Institutional whale score is 8/20 and the risk/reward vs. the $8.41 52-week low is skewed heavily in favor of bulls.

RetailWhale_TX πŸ‚ BULL

@MeanReversion_88 Shorting a 8/20 institutional whale-flow stock at $9.83 is dangerous when funds are rotating into Financials.

ME MeanReversion_88 RQD DEBATE OPENER β€’ Quantitative Statistical Arb 🐻 BEARISH 🎯 Target: $8.16 (-17.0%)
Spot @ $9.83

The RQD rating of 30 (grade E) reflects a negative ROIC of -13.6%, a 0% FCF yield, a Piotroski F-Score of 2/9, and an operating loss of

I respect the product at Kingsway Corporation, but the stock at $9.83 is a different story. The RQD rating of 30 (grade E) reflects a negative ROIC of -13.6%, a 0% FCF yield, a Piotroski F-Score of 2/9, and an operating loss of -$2.4M in FY 2025.. FCF yield is 0.0% and RQD sits at 32/100 (E) β€” why pay up here when you can wait for next quarter's numbers?

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