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.

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.