Anthropic-Cybersecurity-Skills/skills/performing-ssl-tls-security-assessment/SKILL.md

name, description, domain, subdomain, tags, version, author, license

name	description	domain	subdomain	tags	version	author	license
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.	cybersecurity	network-security	network-security ssl tls sslyze certificate cipher-suites vulnerability-assessment	1.0	mahipal	Apache-2.0

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.