What it does. 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. Part of mukul975/Anthropic-Cybersecurity-Skills (817 security skills) (mukul975/Anthropic-Cybersecurity-Skills).

Install

• npx skills add mukul975/Anthropic-Cybersecurity-Skills --skill performing-ssl-tls-security-assessment, or copy the skill folder into ~/.claude/skills/performing-ssl-tls-security-assessment/.
• Raw file: curl -sL https://raw.githubusercontent.com/mukul975/Anthropic-Cybersecurity-Skills/HEAD/skills/performing-ssl-tls-security-assessment/SKILL.md

SKILL.md (verbatim)

name: performing-ssl-tls-security-assessment
description: >-
  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: cybersecurity
subdomain: network-security
tags:
- network-security
- ssl
- tls
- sslyze
- certificate
- cipher-suites
- vulnerability-assessment
version: '1.0'
author: mahipal
license: Apache-2.0
nist_csf:
- PR.IR-01
- DE.CM-01
- ID.AM-03
- PR.DS-02
mitre_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.

Other files in this skill

• LICENSE
• references/api-reference.md
• scripts/agent.py

references/api-reference.md (verbatim)

API Reference: Performing SSL/TLS Security Assessment

sslyze Python API

from sslyze import Scanner, ServerScanRequest, ServerNetworkLocation

location = ServerNetworkLocation(hostname="example.com", port=443)
request = ServerScanRequest(server_location=location)
scanner = Scanner()
scanner.queue_scans([request])

for result in scanner.get_results():
    scan = result.scan_result
    # Access individual scan command results
    tls12 = scan.tls_1_2_cipher_suites
    cert = scan.certificate_info
    heartbleed = scan.heartbleed

Install: pip install sslyze

Scan Command Attributes

Weak Cipher Suite Keywords

sslyze CLI

sslyze example.com --regular
sslyze example.com --certinfo --tlsv1_2 --heartbleed --robot
sslyze example.com --json_out results.json

References

• sslyze GitHub: https://github.com/nabla-c0d3/sslyze
• sslyze Docs: https://nabla-c0d3.github.io/sslyze/documentation/
• sslyze PyPI: https://pypi.org/project/sslyze/
• Mozilla TLS Config: https://wiki.mozilla.org/Security/Server_Side_TLS

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