Agent skill

performing-ssl-tls-security-assessment

Assess SSL/TLS server configurations using the sslyze Python library to evaluate cipher suites, certificate chains, protocol versions, HSTS headers, and known vulnerabilities like Heartbleed and ROBOT.

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Install this agent skill to your Project

npx add-skill https://github.com/mukul975/Anthropic-Cybersecurity-Skills/tree/main/skills/performing-ssl-tls-security-assessment

SKILL.md

Performing SSL/TLS Security Assessment

Overview

Assess SSL/TLS server configurations using sslyze, a fast Python-based scanning library. This skill covers evaluating supported protocol versions (SSLv2/3, TLS 1.0-1.3), cipher suite strength, certificate chain validation, HSTS enforcement, OCSP stapling, and scanning for known vulnerabilities including Heartbleed, ROBOT, and session renegotiation weaknesses.

When to Use

  • When conducting security assessments that involve performing ssl tls security assessment
  • When following incident response procedures for related security events
  • When performing scheduled security testing or auditing activities
  • When validating security controls through hands-on testing

Prerequisites

  • Python 3.9+ with sslyze library (pip install sslyze)
  • Network access to target HTTPS servers on port 443
  • Understanding of TLS protocol versions and cipher suite classifications

Steps

Step 1: Configure Server Scan

Create ServerScanRequest with ServerNetworkLocation specifying target hostname and port.

Step 2: Execute TLS Scan

Use sslyze Scanner to queue and execute scans for all TLS check commands concurrently.

Step 3: Analyze Results

Evaluate accepted cipher suites, certificate validity, protocol versions, and vulnerability scan results.

Step 4: Generate Security Report

Produce a JSON report with compliance findings and remediation recommendations.

Expected Output

JSON report with supported protocols, accepted cipher suites, certificate details, vulnerability results (Heartbleed, ROBOT), and HSTS status.

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