Analyzing TLS Configuration

Overview

This skill audits a target's TLS posture against current best practice (NIST SP 800-52r2, Mozilla TLS Configuration Guidelines, PCI DSS v4.0 Req 4.2.1.1). It reports specific findings — not "your TLS is weak" but "your server negotiated TLSv1.0 with RC4-SHA — see remediation".

When the skill produces findings

Specific failure thresholds, in order of severity:

| Finding | Severity | Threshold | Affected control | |---|---|---|---| | TLSv1.0 or TLSv1.1 negotiated | HIGH | Any handshake completes at v1.0/v1.1 | NIST 800-52r2 §3.1, PCI DSS Req 4.2.1.1 | | Null / EXPORT / anonymous cipher | CRITICAL | Any null / EXPORT / aNULL in negotiated suite | NIST 800-52r2 §3.3.1 | | RC4 / 3DES cipher | HIGH | Sweet32, RC4 biases | NIST 800-52r2 §3.3.1, PCI DSS Req 4.2.1.1 | | Cert expires in <7 days | CRITICAL | notAfter - now ≤ 7d | NIST 800-52r2 §4.1 | | Cert expires in <30 days | HIGH | notAfter - now ≤ 30d | NIST 800-52r2 §4.1 | | Cert hostname mismatch | HIGH | SAN/CN doesn't match target host | RFC 6125 | | Self-signed or untrusted CA | MEDIUM | Chain doesn't validate to system CA | Mozilla TLS Guidelines | | Weak key (RSA < 2048, ECDSA < 256) | HIGH | Public key bits below threshold | NIST 800-52r2 §3.4 | | Forward secrecy absent | MEDIUM | No ECDHE / DHE in negotiated suite | NIST 800-52r2 §3.3.1 |

Prerequisites

• Python 3.9+
• openssl CLI (used for cipher enumeration the Python ssl module can't introspect directly)
• Authorization to test the target (active scan — see references/AUTHORIZATION.md)

Instructions

Step 1 — Confirm Authorization

Active scan. Before invoking the scanner, ask the user verbatim:

> "Do you have authorization to perform TLS testing on this target? > I need confirmation before proceeding."

If the user says yes, proceed. If unsure, ask them to obtain written authorization. See references/AUTHORIZATION.md for the attestation pattern. Never run the scanner against a target the user does not own or have written permission to test.

Step 2 — Run the scanner

bash
python3 ${CLAUDE_PLUGIN_ROOT}/skills/analyzing-tls-config/scripts/analyze_tls.py \
    https://target.example.com \
    --authorized

The --authorized flag is required for any non-loopback / non-RFC1918 target (gate enforced in lib/authz_check.py).

Options:

Usage: analyze_tls.py URL [OPTIONS]

Options:
  --authorized          Attest authorization for non-local targets (required)
  --port PORT           Target port (default: 443)
  --output FILE         Write findings to FILE (default: stdout)
  --format FMT          json | jsonl | markdown (default: markdown)
  --min-severity SEV    Floor: critical|high|medium|low|info (default: info)
  --timeout SECS        Per-probe timeout (default: 10)

Step 3 — Interpret findings

The scanner emits one Finding per detected issue. For each:

1. Read the severity band — CRITICAL and HIGH require immediate action.
2. Read the affected control — map to the framework the user is audited against.
3. Read the remediation — copy-paste-ready config snippets for nginx /

Caddy / Apache / HAProxy / AWS ALB / GCP LB.

1. Cross-reference references/PLAYBOOK.md for the full template if the

inline remediation is just a one-liner.

Step 4 — Report to user

Group findings by severity. For each, lead with the specific symptom ("TLSv1.0 negotiated") rather than the category ("transport security problem"). Pair every finding with one remediation step the user can take in the next 30 minutes.

Step 5 — Cross-skill chaining (optional)

If the user is doing a broader audit:

• After this skill runs, suggest detecting-ssl-cert-issues (skill #2)

for deeper cert-chain analysis (revocation, CT log presence, intermediate-cert order).

• For HTTP-layer security headers that complement TLS findings, suggest

checking-http-security-headers (skill #4) to audit HSTS preload status, which is meaningless without proper TLS.

Examples

Example 1 — SOC2 audit prep on a production endpoint

User says: "Auditor flagged our checkout endpoint for weak TLS. Help me figure out what's wrong."

bash
python3 ${CLAUDE_PLUGIN_ROOT}/skills/analyzing-tls-config/scripts/analyze_tls.py \
    https://checkout.example.com \
    --authorized \
    --min-severity high

Expected output: a Markdown report with each HIGH/CRITICAL finding, the specific NIST/PCI control it violates, and a copy-paste remediation snippet for the target server type. Pair with references/PLAYBOOK.md for full templates.

Example 2 — CI integration on a staging gate

Pin the scan into the deploy pipeline before promotion:

yaml
- name: TLS posture check (staging)
  run: |
    python3 plugins/security/penetration-tester/skills/analyzing-tls-config/scripts/analyze_tls.py \
        https://staging.example.com \
        --authorized \
        --min-severity high \
        --format json \
        --output tls-report.json

Exit code 1 fails the deploy if any HIGH/CRITICAL finding lands. The JSON report uploads as a build artifact for the security team to triage.

Example 3 — Quick local check during dev

For local services (carve-out applies — no --authorized needed):

bash
python3 ${CLAUDE_PLUGIN_ROOT}/skills/analyzing-tls-config/scripts/analyze_tls.py \
    https://localhost:8443

Useful when prototyping TLS-terminating proxies (Caddy, Traefik) before shipping to staging.

Output

Each finding includes:

• skill_id: analyzing-tls-config
• title: imperative — e.g. "Server negotiates obsolete TLSv1.0"
• severity: critical / high / medium / low / info
• target: the URL scanned
• detail: technical explanation of WHY this finding triggered
• remediation: specific fix
• cvss_score / cwe_id: when applicable
• affected_control: framework + control ID (e.g. NIST 800-52r2 §3.1)
• references: source URLs

JSON output is pipeable to jq for CI integration. Markdown output is human-readable for direct sharing with the engineering team.

Exit codes: 0 clean (no high/critical), 1 findings (high or critical), 2 error (auth missing, target unreachable, unparseable input).

Error Handling

--authorized missing for non-local target → exit 2 with attestation message pointing to references/AUTHORIZATION.md. Re-run with the flag after confirming authorization.

Target unreachable → exit 2 with the underlying socket error. Common causes: firewall blocks port 443, DNS resolution failure, server not listening on the configured port (try --port).

Certificate chain incomplete → finding emitted at MEDIUM severity (the scanner does not bail; it captures what was sent and reports the gap).

Resources

• references/THEORY.md — How TLS negotiation works, why each finding

matters, primary RFC references

• references/PLAYBOOK.md — Copy-paste remediation templates per finding

for nginx, Caddy, Apache, HAProxy, AWS ALB, GCP LB

• references/AUTHORIZATION.md — Authorization attestation pattern + ROE

example for active scans