SKWD CLUSTER SEC Filing Analysis

Latest settled — T+20d ⚠ clustered

SKWD ▼ -9.34% at T+20d

LONG call ✗ call lost -9.34% · α vs SPY -1.78% · entry $46.47 → $42.13

Next anchor: T+60d due yesterday

Last close $47.45 (close May 22) · +2.11% from $46.47 entry

Entry anchored
Feb 26, 03:59 PM ET
via Databento tick

T+1d

+4.54%

call +4.54% · α +4.49%

$48.58

settled 3mo ago

T+5d

+4.82%

call +4.82% · α +6.80%

$48.71

settled 3mo ago

T+20d

-9.34%

call -9.34% · α -1.78%

$42.13

settled 8w ago

T+60d

—

call — · α —

—

due yesterday

Price Chart

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Executive Summary

Skyward Specialty executives, including CEO Andrew Robinson and CFO Mark Haushill, engaged in a cluster of insider transactions over the past week. The key activity was open-market share purchases totaling over $650K by the CEO and Apollo's CFO, signaling confidence, while other executives had routine tax-related share withholdings and option exercises with no cash impact.

Key Financial Metrics

Direction

buying

Total Value

$659.7K

Insiders

7

Actionable Insight

The CEO's substantial personal purchase is a strong vote of confidence, especially in a stable or down market. Traders should watch for follow-on buying and any upcoming earnings commentary.

Key Facts

CEO Andrew Robinson purchased $503,934 worth of shares in the open market.
Apollo's CFO Taryn McHarg bought $4,671 of SKWD shares, signaling external confidence.
Total open-market purchases in the cluster: $659,665.
Multiple executives exercised stock options and had shares withheld for taxes, a routine non-cash event.
No open-market sales occurred in the cluster.

Financial Impact

$659,665 in net insider buying over 7 days, representing 0.033% of $2.0B market cap

insider sentimentmarket confidence

Risk Factors

The dollar amount, while meaningful, is still small relative to market cap (<0.1%)
Tax withholdings and option exercises are routine and should not be interpreted as sentiment signals

Market Snapshot

Exchange

Nasdaq

Documents Analyzed

This report is based on 1 SEC document filed with EDGAR.

Document	Accession Number
CONTEXT: Insider Cluster Data (15 trades, 7d window)	cluster-SKWD-1772561399210

6 reports for SKWD

T+1T+5T+20T+60

75% Hit rate 3 of 4 directional calls best @ T+5▲ +4.82%Feb 27, 2026

Filters

Reports for SKWD — sortable, filterable
	Type				Now
May 6, 2026 17d ago	8-K BULLISH ★ 6/10	$45.51 $44.03	▼ −3.25%	▼ −4.76%	$47.45 (+4.26%)
May 6, 2026 17d ago	Press Release BULLISH ★ 7/10	$45.51 $44.03	▼ −3.25%	▼ −4.76%	$47.45 (+4.26%)
Mar 25, 2026 8w ago	DEFA14A NEUTRAL ★ 3/10	$43.15 $43.07	▼ −0.19%	▲ +0.06%	$47.45 (+9.97%)
Feb 27, 2026 12w ago	Insider Cluster BULLISH ★ 7/10	$46.47 $48.71	▲ +4.82%	▲ +6.80%	$47.45 (+2.11%)
Feb 27, 2026 12w ago	Insider Cluster BULLISH ★ 7/10	$46.47 $48.71	▲ +4.82%	▲ +6.80%	$47.45 (+2.11%)
Feb 27, 2026 12w ago	Insider Cluster BULLISH ★ 7/10	$46.47 $48.71	▲ +4.82%	▲ +6.80%	$47.45 (+2.11%)

US Market Status

Market Closed — Opens Tue (35h 12m)

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