Individual skill
detecting-ssl-cert-issues
Audit a target's TLS certificate beyond protocol/expiry — chain ordering, OCSP stapling, revocation status, Certificate Transparency presence, key-usage flags, and over-broad wildcards. Use when: TLS handshake already passes (skill #1 analyzing-tls-config cleared) but you suspect the cert posture is fragile. Auditors flag this during SOC2 readiness when a renewal slipped or an intermediate was rotated. Threshold: missing OCSP stapling on production, fewer than 2 SCTs in the cert, intermediate served out of order, key usage missing digitalSignature/keyEncipherment, revoked cert presented, or wildcard scope of 2-level (e.g., *.com is rejection; *.api.example.com is fine). Trigger with: "check cert revocation", "audit ocsp", "ct log check", "cert chain audit".
plugins/security/penetration-tester/skills/detecting-ssl-cert-issues/SKILL.md
Source commit 0500b275e963c027f6b410e8c49c0446945c574e
What was checked
- Matches the observed repository HEAD
- Yes
- Scanner rules are current
- No
- Repository scan complete
- No
- Skill scan complete
- No
- Observed behavior
- Not checked yet
- Last checked
- Nov 12, 2026
These are observations at the recorded commit, not a guarantee of safety. Review the source before running it.
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Repository context
- Repository stars (not skill ratings)
- 2,917
- Repository last updated
- Nov 12, 2026
- License
- MIT
Observed agent integration: No specific integration evidence. Standard SKILL.md installation does not imply verified compatibility.
- ai Repository topic
- automation Repository topic
- claude-code Repository topic
- devops Repository topic
- mcp Repository topic
- ai-agents Repository topic
- anthropic Repository topic
- claude-code-plugins Repository topic
- developer-tools Repository topic
- llm Repository topic
- security Declared skill tag
- tls Declared skill tag
- ocsp Declared skill tag
- certificate-transparency Declared skill tag
- pentest Declared skill tag
- security Derived category
Files and excerpt
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Browse files
SKILL.mdcore · 6,903 bytesSKILL.mdcore · 6,903 bytesSKILL.mdcore · 6,903 bytesSKILL.mdcore · 6,903 bytesSKILL.mdcore · 6,903 bytesreferences/PLAYBOOK.mddoc · 5,160 bytesreferences/THEORY.mddoc · 5,907 bytesscripts/check_cert_chain.pyruns · 17,520 bytes
Read excerpt
# Detecting SSL Certificate Issues
## Overview
This skill is the second-level cert audit, run after `analyzing-tls-config`
clears the protocol+cipher+expiry+hostname basics. It surfaces issues
that don't break the handshake today but make the cert fragile or open
to soft-bypass attacks: missing OCSP stapling forces clients to phone
home to the CA (privacy + latency hit), missing Certificate Transparency
SCTs are rejected by Chrome since 2018, an out-of-order chain confuses
older clients, and over-broad wildcards expand the blast radius of any
future key compromise.
## When the skill produces findings