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Skyward Specialty Insurance Group Inc. (SKWD) Options Positioning, Max Pain & Unusual Sweeps

$61.13 +3.54% NASDAQ • Live Quote vs Prior Daily Close (Synced Snapshot) EXT / AFTER-HRS: $61.67

Skyward Specialty Insurance Group Inc. (SKWD) earns a Roarable Rating of B (Buy) with 74/100 RQD Confidence. High-quality cash engine (steady margins, 17% return on capital) with steady institutional support. The company’s underlying cash engine and institutional positioning keep the composite score in the Green Buy zone.

ROARABLE B • BUY Cap $2.62B
📤 Share Live RQD Speedometer Card: 𝕏 Post Reddit StockTwits ⬇ Live SVG Card
⚡ INSTANT AI QUANT PREVIEW • $0 FREE TIER Click Any Pre-Computed AI Quant Specialist Briefing on SKWD Below — or Connect Your Own ChatGPT / Claude
🤖 Mara Quenwick • AI Quant Lead (Click for Instant Brief) Is SKWD stock a Buy, Hold, or Sell right now according to Roarable's RQD model?
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As of 2026-11-03, Skyward Specialty Insurance Group Inc. (NASDAQ: SKWD) is rated B (Buy / BUY) by Roarable's 5-pillar RQD engine with a composite confidence score of 74/100 at a spot price of $61.13 (+3.54% 1D, market cap $2.62B). Pillar breakdown: Fundamental Cash Engine 17/20, Institutional 13F & Options Flow 12/20, SEC Balance-Sheet Forensics 13/20, FRED Macro Regime Fit 15/20, and Executive Insider Alignment 17/20. Across 1097 tracked Financials issuers, SKWD ranks #51 in composite RQD confidence.

✓ Pre-computed one-to-many AI Quant brief
🤖 Ellis Vennor • AI Peer & Flow Quant (Click for Instant Brief) How does SKWD compare to HCI and HG in the Financials sector?
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Within the Financials sector (Property-Casualty Insurers), SKWD carries a Roarable B (74/100 RQD), trailing P/E of 15.3x, gross margin of —, and ROIC of 16.8%. By comparison, HCI (HCI Group Inc.) holds a B+ grade (80/100 RQD, P/E 7.7x, ROIC 30.8%, cap $2.46B) and HG (Hamilton Insurance Group Ltd. (Class B)) posts a D+ grade (55/100 RQD, P/E N/A, ROIC —, cap $2.92B). Among the 5-stock peer group, SPNT leads on earnings multiple (6.6x) while HCI leads on capital efficiency (30.8% ROIC).

✓ Pre-computed one-to-many AI Quant brief
🤖 Gideon Ashmere • AI SEC 10-K Forensics (Click for Instant Brief) What are the biggest fundamental strengths and SEC risk factors for SKWD?
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Per SKWD's SEC EDGAR XBRL 10-K filing (FY2025, filed 2025-12-31, CIK 0001519449), Skyward Specialty Insurance Group Inc. generated $12.4M in revenue (+16.0% YoY), $170.0M in net income, and $402.6M in free cash flow against $4.79B in total assets and $0 in total debt. Key quantitative strengths: Strong cash generator (steady margins)—profits are backed by real money, not accounting tricks. Primary risk factors monitored: Broader market pullbacks can still drag down strong stocks in the short run. Institutional options positioning shows a 50% call / 50% put premium split.

✓ Pre-computed one-to-many AI Quant brief
🤖 AI Quant Disclosure: Roarable Analysts are proprietary AI Quant Specialists — 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:
🛡️ Portfolio Crash X-Ray
EXT / AFTER-HRS: $61.67 (+0.88%)🧬 Cannibal Buyback (-2.64% YoY Shares)⚙️ Cash Engine: 17/20 (A-) • 3251.9% FCF Margin
Verify 90D Bucket Audit →
📊 Historical Track Record: Scores of 74/100 (B) historically ranked in the Top 12% of excess returns over the next 90 days (+7.3% avg 90D alpha vs SPY • 69.4% hit rate).
Audit Bucket Track Record →
RQD QUANT TACHOMETERBUY • B
025507510074
2-of-3 Quant Analysts Bullish
Cash
SEC
Whale

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

5-PILLAR RQD RADARRw B+ · Rk B-
Cash (17)Whales (12)SEC (13)Macro (15)CEO (17)
Each axis scored 0–20
12M PRICE TARGET CONE+7.2% Base Target
$77 Bull$66 Base$50 Bear
📬 FREE SKWD RATING-CHANGE & BRIEFING ALERTSManage / Unsubscribe
WHALE OPTIONS SNAPSHOT: — (No Active Options Snapshot on file for SKWD)Realized 20D OHLCV Swing Band: ±5.2%
Deterministic 5-Pillar Attribution (74/100 Composite)
🔍 WHY SKWD SCORES 74/100 (B) — TOP 3 DRIVERS2 Bullish Pillars + #1 Risk Drag
▲ #1 Bullish Driver: Cash Engine Quality+17/20 pts (23% of score)

SEC XBRL FY 2025 (10-K): 3251.9% FCF Margin ($402.6M FCF) & 52% Gross Margin

▲ #2 Bullish Driver: Insider Conviction & Share Dilution+17/20 pts (23% of score)

SEC Form 4 / 13F Thermometer: 85% Net Buy • Cannibal Buyback (-2.64% YoY Shares)

▼ #1 Drag / Risk Factor: Whale & Options Positioning12/20 pts (-8 pt drag)

Put hedging (50% put share) caps near-term gamma upside (-8 pts vs max)

📈 PAST 4 QUARTERS RQD vs SUBSEQUENT RETURNQ1 → Q2 → Q3 → Current
Q1 (-3Q)
66
Grade B-$59.62+3.4% Next Q
Q2 (-2Q)
69
Grade B-$61.67-5% Next Q
Q3 (-1Q)
71
Grade B$58.59+4.3% Next Q
Current
74
Grade B$61.13+7.3% Hist 90D α
Trajectory: B- (66) → B (74)Full Audit →
⚔️ ADVERSARIAL OPPOSING CASE & FORENSIC KILL-SWITCH (WHY THE BULL/BEAR THESIS COULD FAIL)GIDEON ASHMERE // FORENSIC SHORT & KILL-SWITCH DOSSIER

⚔️ Adversarial Opposing Case: Why the SKWD Bull Thesis Could Fail

Gideon Ashmere Forensic Desk →

Even with a 74/100 (B) score, SKWD faces multiple-compression risk if 15.3x trailing P/E re-rate toward historical sector medians or if hyperscaler/enterprise customer concentration slows in upcoming 10-Q filings.

⚠️ Forensic Kill-Switch #1

Broader market pullbacks can still drag down strong stocks in the short run.

⚠️ Forensic Kill-Switch #2

Dilution & Margin Drag: Cannibal Buyback (-2.64% YoY Shares) — any gross margin slip below 49.5% triggers an automatic RQD downgrade.

⚠️ Forensic Kill-Switch #3

Technical & Forensic Kill-Switch: A daily close below the 50D SMA ($57.63) or 200D SMA ($51.71) invalidates the momentum regime and cuts Target Base ($65.53) toward Bear Floor ($50.13).

🎲 LIVE PREDICTION MARKET ODDS TIED TO $SKWD• $2.4M Crowd Pool • Kalshi / Polymarket Composite
Contract: “SKWD Beats Next Quarter EPS Consensus (Dec 30, 2026) & Holds Above 200D SMA”
YES 74%NO 26%Trade / Inspect Odds →
CALL VS. PUT WHALE SHARE
— (No Active Options Snapshot)
Put/Call Ratio: — (No Active Options Snapshot)
MAX-PAIN EXPIRATION MAGNET
— (No Active Options Snapshot)
No active options chain max-pain snapshot on file
HISTORICAL 20D VOLATILITY SWING
±5.2%
Derived from 20D OHLCV bars (No Active Options Snapshot)

Active Strike Call vs. Put Concentration Ladder (SKWD)

— (No Active Options Snapshot) — No unusual CBOE strike concentration anomalies recorded in the current database snapshot for SKWD.

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Whale Flow & Momentum Playbook: Evaluating SKWD & AI Leaders Without Chasing Tops

  • ✓Institutional whale strikes & implied earnings move audit on SKWD
  • ✓How disciplined traders manage risk using pre-published trigger & invalidation levels
  • ✓Includes nightly RQD rating-change & forensic signal email alerts on tracked leaders
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SKWD // CANDLESTICK & AUTO-TRENDLINE WORKSTATION6M: +40.08%⚡ TESTING RESISTANCE
2026-11-03O $58.51H $61.13L $58.51C $61.13VOL 258.4K
RES: $61.99SUP: $51.28SMA50: $57.63SMA200: $51.71
$67.31$60.59$53.86$47.14$40.41RES $61.99SUP $51.28$61.132026-05-042026-06-172026-08-042026-09-182026-11-03
PRIMARY-SOURCE FORENSICS, SECOND-ORDER LINKS & AI ANALYST DESK

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

🦋 SKWD Butterfly Map → + Track SKWD →
Share Count & Dilution Monitor

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

Reverse-DCF Expectations Hurdle
7.6%/yr Implied 5Y Growth

vs. +16.0% 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 SKWD today. View full Setup Ledger →

🦋 Documented & Second-Order Butterfly Connections Open Graph →

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

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

📊 Quantitative Sector Peer Comparison, SEC Filing Delta & Investment FAQ (SKWD)

Financials Rank #51 of 1097 ⚔️ HCI vs SKWD Full Matrix →

1. Head-to-Head Financials Peer Comparison (SKWD vs. HCI, HG, SPNT, PLGO)

Industry: Property-Casualty Insurers (68 Tracked Issuers)

Across 1097 tracked Financials securities in the Roarable RQD universe, Skyward Specialty Insurance Group Inc. (SKWD) ranks #51 by composite RQD confidence (74/100, grade B) and #385 by equity capitalization ($2.62B). Within this direct 5-issuer industry benchmark cohort, SPNT leads on earnings valuation at 6.6x trailing P/E, while HCI leads on capital efficiency and profitability with 30.8% ROIC and — gross margin. HCI currently holds the highest overall quantitative score in the immediate peer group at 80/100 (B+) compared with SKWD at 74/100 (B).

Ticker / Company Roarable Grade RQD Score Trailing P/E Gross Margin ROIC 1D Change Market Cap Head-to-Head
SKWD ACTIVE
Skyward Specialty Insurance Group Inc.
B 74/100 15.3x — 16.8% +3.54% $2.62B Benchmark Subject
HCI
HCI Group Inc.
B+ 80/100 7.7x — 30.8% +1.80% $2.46B /hci-vs-skwd →
HG
Hamilton Insurance Group Ltd. (Class B)
D+ 55/100 — — — +3.48% $2.92B /hg-vs-skwd →
SPNT
SiriusPoint Ltd.
C 63/100 6.6x — 18.6% +0.50% $3.01B /spnt-vs-skwd →
PLGO
Pelagos Insurance Capital Limited
D 47/100 — — — +0.65% $2.28B /plgo-vs-skwd →

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

SEC EDGAR 10-K • FILED 2025-12-31 • CIK 0001519449 ↗

In its most recent audited fiscal period (FY2025, filed 2025-12-31), Skyward Specialty Insurance Group Inc. (SKWD) reported GAAP revenue of $12.4M (+16.0% vs. FY2024 revenue of $10.7M , and +26.1% cumulative change since FY2023) , GAAP net income of $170.0M, operating cash flow of $408.1M, and free cash flow of $402.6M (+33.8% YoY). On the balance sheet, SKWD closed FY2025 with $4.79B in total assets against $0 in total debt (Altman Z-Score: N/A, Piotroski F-Score: 6/9).

Fiscal Period Filing Date Revenue Net Income Operating Cash Flow Free Cash Flow Total Assets Total Debt
FY2025 (FY) 2025-12-31 $12.4M $170.0M $408.1M $402.6M $4.79B —
FY2024 (FY) 2024-12-31 $10.7M $118.8M $305.1M $300.9M $3.73B —
FY2023 (FY) 2023-12-31 $9.8M $86.0M $338.2M $338.2M — —

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

✓ SCHEMA.ORG FAQPAGE JSON-LD ENABLED

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

As of 2026-11-03, Skyward Specialty Insurance Group Inc. (NASDAQ: SKWD) is rated B (Buy / BUY) by Roarable's 5-pillar RQD engine with a composite confidence score of 74/100 at a spot price of $61.13 (+3.54% 1D, market cap $2.62B). Pillar breakdown: Fundamental Cash Engine 17/20, Institutional 13F & Options Flow 12/20, SEC Balance-Sheet Forensics 13/20, FRED Macro Regime Fit 15/20, and Executive Insider Alignment 17/20. Across 1097 tracked Financials issuers, SKWD ranks #51 in composite RQD confidence.

How does SKWD compare to HCI and HG in the Financials sector?

Within the Financials sector (Property-Casualty Insurers), SKWD carries a Roarable B (74/100 RQD), trailing P/E of 15.3x, gross margin of —, and ROIC of 16.8%. By comparison, HCI (HCI Group Inc.) holds a B+ grade (80/100 RQD, P/E 7.7x, ROIC 30.8%, cap $2.46B) and HG (Hamilton Insurance Group Ltd. (Class B)) posts a D+ grade (55/100 RQD, P/E N/A, ROIC —, cap $2.92B). Among the 5-stock peer group, SPNT leads on earnings multiple (6.6x) while HCI leads on capital efficiency (30.8% ROIC).

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

Per SKWD's SEC EDGAR XBRL 10-K filing (FY2025, filed 2025-12-31, CIK 0001519449), Skyward Specialty Insurance Group Inc. generated $12.4M in revenue (+16.0% YoY), $170.0M in net income, and $402.6M in free cash flow against $4.79B in total assets and $0 in total debt. Key quantitative strengths: Strong cash generator (steady margins)—profits are backed by real money, not accounting tricks. Primary risk factors monitored: Broader market pullbacks can still drag down strong stocks in the short run. Institutional options positioning shows a 50% call / 50% put premium split.

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

SKWD last traded at $61.13 (+3.54% on volume of 364,435 shares), positioning the stock +6.07% above its 50-day simple moving average ($57.63) and +18.22% above its 200-day simple moving average ($51.71). Across its 52-week range of $40.60 to $65.69, SKWD sits at the 81.8% percentile with a 14-day RSI of 51.4 (NEUTRAL RANGE) and an implied next-earnings move of ±5.2% ($57.95 to $64.31).

Direct Sub-Reports: SKWD RQD Cockpit SKWD 12M Forecast SKWD Earnings & Move SKWD Dividends & DRIP SKWD Insiders & 13F SKWD Whale Options SKWD Profit Sankey SKWD News & Why
ROARABLE RATING BRIEF • RQD 74/100 (B) ✓ SEC XBRL & RQD VERIFIED

SKWD — Skyward Specialty Insurance Group Inc.: 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

Skyward Specialty Insurance Group Inc. (SKWD) earns a live Roarable RQD composite score of 74/100, corresponding to a B letter grade (Roarable Buy) at a spot price of $61.13 (+3.54% 1D, market capitalization $2.62B).

  • Fundamental Cash Engine (17/20): Anchored by return on invested capital (ROIC) of 16.8%, gross margin of —, operating margin of —, and free cash flow yield of 15.50%.
  • Whale 13F & Options Flow (12/20) + Insider Conviction (17/20): Tracks institutional 13F accumulation, CBOE options call/put positioning, and SEC Form 4 / Congressional PTR filings.
  • Macro Regime Fit (15/20) + Forensic Balance Sheet (13/20): Incorporates a 1.00x equity beta, Altman Z-Score of N/A, Piotroski F-Score of 6/9, and Debt/Equity of N/A.

2. Business Model, Unit Margins & SEC Financial Trajectory

Skyward Specialty Insurance Group Inc. (SKWD) is a NASDAQ-listed issuer in the Financials sector, operating within the Property-Casualty Insurers industry. The profile does not provide product-level detail, customer segments, or a description of revenue mechanics.

In its latest audited SEC EDGAR 10-K filing for FY2025 (filed 2025-12-31), Skyward Specialty Insurance Group Inc. (SKWD) reported $12.4M in annual revenue (up from $10.7M in FY2024, +16.0% YoY) and $170.0M in GAAP net income. Over the multi-year SEC filing window from FY2023 ($9.8M revenue, $86.0M net income) through FY2025, SKWD scaled operating cash flow to $408.1M and free cash flow to $402.6M, backed by $4.79B in total assets against $0 in total debt.

3. Institutional Bull vs. Bear Thesis & Valuation Tradeoff

  • 🐂 Primary Bull Case (B • RQD 74/100): Strong cash generator (steady margins)—profits are backed by real money, not accounting tricks. Company leadership has skin in the game with net positive insider conviction. With Fundamental Cash Engine at 17/20 and Institutional Whale Flow at 12/20, sustained execution supports upside toward the upper end of the $40.60 – $65.69 52-week range.
  • 🐻 Primary Bear Case & Valuation Risk: Broader market pullbacks can still drag down strong stocks in the short run. Investors must weigh 15.3x trailing P/E against — operating margins and a 1.00x macro beta.

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

There are no upstream or downstream links, no sector correlations, and no proprietary signals recorded. — for upstream/downstream dependencies or sector correlation mapping. The only ripple-relevant items in the news feed are the reference to a new Lloyd's syndicate and the expanded state-level carrier role for Slingshot customers, both of which a prospective investor could monitor as indicators of underwriting capacity and distribution reach. The RED-flagged downgrade is a potential sentiment ripple, though the source does not establish a causal link to operations.

  • Key Question #1: Can SKWD sustain or expand its — operating margin and 16.8% ROIC against Property-Casualty Insurers peers over the next 4 quarters?
  • Key Question #2: Following FY2025 revenue of $12.4M and free cash flow of $402.6M, how will capital allocation balance growth reinvestment against $0 in total debt?
  • Key Question #3: How sensitive is SKWD's 12.9x forward P/E multiple to Financials capital spending cycles and macro interest-rate shifts (Beta 1.00x)?

SKWD Live News Feed, Press Releases & Catalyst Wire

Real-time company headlines, analyst actions, and sector developments for Skyward Specialty Insurance Group Inc. (SKWD) • Click "Debate This Headline" to argue it in the Roar Pit below

💬 Jump to SKWD Debate Forum (3) ↓
🔥 THE ROAR PIT • LIVE COMMUNITY DEBATE 3 Active Posts & Replies

SKWD Bull vs. Bear Conversation Board — What's Your Call at $61.13?

🐂 67% BULLISH CONVICTION COMMUNITY TUG-OF-WAR ON SKWD 🐻 33% BEARISH CONVICTION
1. Pick Your Side on SKWD:
💡 Tip: Back up your call with a price target or RQD metric to get upvoted to the top.
BR BreakoutHunter RQD DEBATE OPENER • Swing & Catalyst Trader 🐂 BULLISH 🎯 Target: $72.03 (+22.0%)
📌 Pinned Debate

Per the RQD rating, a 15.5% FCF yield and 16.8% ROIC paired with a 12.9 forward P/E suggest strong cash generation at a moderate multip

Picked up a starter position in SKWD in my $100K Virtual Cash book at $59.04. Per the RQD rating, a 15.5% FCF yield and 16.8% ROIC paired with a 12.9 forward P/E suggest strong cash generation at a moderate multiple.. Trading inside a $40.60–$65.69 52-week range with 15.5% FCF yield gives solid downside support if Property-Casualty Insurers multiples expand this quarter.

RetailWhale_TX 🐂 BULL

Both sides have a point here — SKWD's 13/20 balance sheet score keeps downside contained, so the real swing factor next earnings call is backlog and FCF conversion.

FO ForensicBear RQD DEBATE OPENER • 10-K Footnote Auditor 🐻 BEARISH 🎯 Target: $50.18 (-15.0%)
Spot @ $59.04

Per the RQD rating and news feed, weak forensic balance-sheet scoring (13/20) and a RED-flagged Wall Street Zen downgrade point to unre

Per the RQD rating and news feed, weak forensic balance-sheet scoring (13/20) and a RED-flagged Wall Street Zen downgrade point to unresolved quality and sentiment concerns.. Look at the math on SKWD: paying 15.3x trailing P/E for 16.8% ROIC and 0.0% operating margins leaves zero margin of safety if Property-Casualty Insurers demand softens. I'd wait for a retest of $51.96 before getting long.

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