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performing-ssl-tls-security-assessment

Assess SSL/TLS server configurations using the sslyze Python scanning library to evaluate supported protocol versions, cipher suite strength, certificate chain validation, HSTS enforcement, OCSP stapling, and known vulnerabilities such as Heartbleed and ROBOT. Use when conducting a security assessment of a server's TLS configuration or verifying remediation of cipher/certificate weaknesses.

Published by mukul975 ↗mukul975/Anthropic-Cybersecurity-Skills

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performing-ssl-tls-security-assessment

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Use performing-ssl-tls-security-assessment to assess [authorized HTTPS hostname] and produce a JSON report of protocols, ciphers, certificate details, HSTS, and vulnerability findings with remediation recommendations.

Required inputs

  • [authorized HTTPS hostname]

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SKILL.md

name: performing-ssl-tls-security-assessmentdescription: >-  Assess SSL/TLS server configurations using the sslyze Python scanning  library to evaluate supported protocol versions, cipher suite strength,  certificate chain validation, HSTS enforcement, OCSP stapling, and known  vulnerabilities such as Heartbleed and ROBOT. Use when conducting a security  assessment of a server's TLS configuration or verifying remediation of  cipher/certificate weaknesses.domain: cybersecuritysubdomain: network-securitytags: - network-security- ssl- tls- sslyze- certificate- cipher-suites- vulnerability-assessmentversion: '1.0'author: mahipallicense: Apache-2.0nist_csf: - PR.IR-01- DE.CM-01- ID.AM-03- PR.DS-02mitre_attack: - T1046- T1040- T1557- T1071- T1553

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.