checkra1n vs Trail of Bits Software Assurance: side-by-side comparison (2026)
checkra1n is a free penetration testing solution. Trail of Bits Software Assurance is a commercial penetration testing solution by Trail of Bits. Features, integrations, deployment and the company behind each one, side by side.
Semi-tethered jailbreak for iPhone 5s to iPhone X, running iOS 12.0 and up, using the 'checkm8' bootrom exploit.
Multi-disciplinary security assessment service spanning app-sec, crypto, blockchain
Side-by-side comparison
Feature
checkra1n
Trail of Bits Software Assurance
Pricing model
Free
Commercial
Category
Penetration Testing
Penetration Testing
Deployment and fit
Deployment type
On-Premises
On-Premises
Company size fit
–
Mid-Market, Enterprise
Company
Company
–
Trail of Bits
Use cases and capabilities
Linux
Yes
No
macOS
Yes
No
iOS
Yes
No
Windows
Yes
No
Penetration Testing Framework
No
Yes
Source Code Analysis
No
Yes
Fuzzing
No
Yes
Threat Modeling
No
Yes
Vulnerability Research
No
Yes
CI/CD
No
Yes
LLM Security
No
Yes
Security Audit
No
Yes
Secure Development
No
Yes
Core features
No features listed
1 feature listed
Integrations
No integrations listed
3 integrations listed
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