Is SKWD or TRUP more undervalued in 2026?

CirclFi compares Skyward Specialty Insurance Gro (SKWD) and Trupanion, Inc. (TRUP) using 13 institutional-grade valuation models. SKWD has a Quality of Company score of 9.9/10 while TRUP scores 8.3/10.

Which is a better buy — SKWD or TRUP?

Compare intrinsic values from 13 independent models against current market prices. CirclFi also calculates Value Trap scores. This is not financial advice — conduct your own analysis.

How do SKWD and TRUP valuations compare?

SKWD at $44.77 and TRUP at $22.15 are compared across Bayesian DCF, EPV, EROIC Spread, First Chicago, Markov DDM, and 8 additional models.

SKWD vs TRUP Valuation Comparison 2026 — Intrinsic Value Analysis

SKWD

Insurance - Property & Casualty

Skyward Specialty Insurance Gro

Quality

9.9

out of 10

Value Trap

SAFE

Price

$44.77

Last close

Models

12/13

Active

TRUP

Insurance - Property & Casualty

Trupanion, Inc.

Quality

8.3

out of 10

Value Trap

SAFE

Price

$22.15

Last close

Models

11/13

Active

Model-by-Model Comparison

Model	Type	SKWD Fair Value	SKWD Upside	TRUP Fair Value	TRUP Upside
Bayesian DCF	Intrinsic	$180.94	+304.2%	$20.31	-8.3%
Earnings Power Value	Intrinsic	$21.41	-52.2%	$3.90	-82.4%
EROIC Spread	Intrinsic	$•••.••	••.•%	$•••.••	••.•%
First Chicago	Scenario	$•••.••	••.•%	$•••.••	••.•%
Markov DDM	Intrinsic	$•••.••	••.•%	$•••.••	••.•%
ML-RIV	Intrinsic	$•••.••	••.•%	$•••.••	••.•%
PWERM	Option-Based	$•••.••	••.•%	$•••.••	••.•%
Regime Cross-Sectional	Relative	$•••.••	••.•%	$•••.••	••.•%
Sentiment SOTP	Hybrid	$•••.••	••.•%	$•••.••	••.•%
CUCE Ensemble	Ensemble	$•••.••	••.•%	$•••.••	••.•%
FTNN Topology	Relative	$•••.••	••.•%	$•••.••	••.•%
RCMH-DCF	Intrinsic	$•••.••	••.•%	$•••.••	••.•%

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SKWD vs TRUP — Which Stock Is More Undervalued?

SKWD scores higher with a 9.9/10 quality rating vs TRUP's 8.3/10. Both stocks are analyzed daily using SEC EDGAR filings across 13 independent models.

Comparing Skyward Specialty Insurance Gro (SKWD) and Trupanion, Inc. (TRUP) across 13 institutional-grade valuation models reveals how each company's intrinsic value stacks up against its market price. CirclFi's engine processes SEC EDGAR 10-K and 10-Q filings, FRED macroeconomic data, and GDELT news sentiment to generate independent fair value estimates daily.

SKWD currently trades at $44.77 with a QOC of 9.9/10, while TRUP trades at $22.15 with a QOC of 8.3/10.

Both companies are analyzed with models spanning intrinsic (Bayesian DCF, EPV), scenario-based (First Chicago), regime-switching (Markov DDM, RCMH-DCF), machine learning (ML-RIV, FTNN Topology), and ensemble methods (CUCE).