performing-ssl-tls-security-assessment

Assess SSL/TLS misconfigurations and certificate issues on HTTPS endpoints.

Updated Apr 23, 2026
One-click install
npx skills add https://github.com/YukiIto1999/ctf-sleuth --skill performing-ssl-tls-security-assessment
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: performing-ssl-tls-security-assessment
Source: https://github.com/YukiIto1999/ctf-sleuth/tree/main/.claude/skills/performing-ssl-tls-security-assessment
Command: npx skills add https://github.com/YukiIto1999/ctf-sleuth --skill performing-ssl-tls-security-assessment

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill requires sslyze, and includes scripts (resource) and references (resource) components.

What problem does it solve?

SSL/TLS configurations often have weak ciphers, deprecated protocol versions, and misconfigured certificates that expose services to risk. This skill automates the assessment to surface these issues across HTTPS endpoints.

Core Features & Use Cases

  • Evaluate supported protocol versions, cipher suites, and certificate details using sslyze to determine overall TLS health.
  • Detect common misconfigurations and vulnerabilities (Heartbleed, ROBOT, OCSP stapling, HSTS) and generate actionable remediation guidance.
  • Produce a structured JSON report summarizing results for compliance reviews, risk dashboards, and incident response workflows.

Quick Start

Run the SSL/TLS security assessment against a target host:port to generate a machine-readable report.

Frequently Asked Questions about performing-ssl-tls-security-assessment

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I automate an SSL/TLS security assessment for HTTPS endpoints?

To automate an SSL/TLS security assessment, you can use this Skill to scan target servers and generate a structured JSON report detailing protocols, ciphers, certificates, and vulnerabilities. It leverages the sslyze library to evaluate supported protocol versions and certificate details.

Can I detect vulnerabilities like Heartbleed and ROBOT during an SSL certificate scan?

Yes, an SSL certificate scan can detect common misconfigurations and vulnerabilities like Heartbleed, ROBOT, OCSP stapling, and HSTS issues. The Skill evaluates TLS health using sslyze and generates actionable remediation guidance.

What is the best way to generate a machine-readable report for TLS compliance reviews?

The best way to generate a machine-readable report for TLS compliance reviews is to run this Skill against your target hosts. It produces a structured JSON summarizing protocols, ciphers, and vulnerabilities, suitable for risk dashboards and incident response workflows.

Do I need Python and network access to check for weak ciphers and deprecated protocol versions?

Yes, you need Python 3.9+, the sslyze library, and network access to port 443 to check for weak ciphers and deprecated protocol versions. These prerequisites allow the Skill to evaluate supported protocol versions and certificate details on target servers.

Why does my TLS health check fail on servers without open port 443?

Your TLS health check fails because the Skill requires network access to port 443 to evaluate supported protocol versions, cipher suites, and certificate details. Without this access, the sslyze library cannot communicate with target servers to identify misconfigurations.

When do I need to perform an SSL/TLS security assessment on production servers?

You need to perform an SSL/TLS security assessment during security audits, compliance reviews, and ongoing monitoring of production servers. This Skill surfaces weak ciphers, deprecated protocol versions, and misconfigured certificates that expose HTTPS endpoints to risk.