Checking HTTP Security Headers

Overview

HTTP response headers are the cheapest defense-in-depth layer most web

apps ship. Each header closes one specific attack class — HSTS forces

HTTPS, CSP blocks script injection, X-Frame-Options blocks clickjacking,

etc. Missing headers don't break the app; they just leave the attack

class open. This skill probes for the presence + value correctness of

the canonical security-relevant headers.

When the skill produces findings

Prerequisites

• Python 3.9+
• Authorization for non-local targets

Instructions

Step 1 — Confirm authorization

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

Step 2 — Run the scanner

python3 ${CLAUDE_PLUGIN_ROOT}/skills/checking-http-security-headers/scripts/check_headers.py \
    https://example.com \
    --authorized

Options:

Usage: check_headers.py URL [OPTIONS]

Options:
  --authorized       Attest authorization (required for non-local)
  --output FILE
  --format FMT       json | jsonl | markdown (default: markdown)
  --min-severity SEV (default: info)
  --timeout SECS     Per-probe timeout (default: 10)
  --authenticated    Treat as authenticated endpoint (stricter Cache-Control gate)

Step 3 — Interpret findings

HIGH = open exploitable class (no HSTS = MITM downgrade open; no CSP =

XSS class wide open; no clickjacking guard = UI-redress attacks).

MEDIUM/LOW = posture hardening.

Step 4 — Cross-skill chaining

• After this skill, suggest auditing-cors-policy (#3) — CSP and CORS

interact; certain CSP directives need matching CORS headers.

• For HSTS preload submission, see references/PLAYBOOK.md § HSTS

preload checklist.

Examples

Example 1 — Mozilla Observatory grade improvement

User: "Observatory gives us a D. What's missing?"

python3 ${CLAUDE_PLUGIN_ROOT}/skills/checking-http-security-headers/scripts/check_headers.py \
    https://example.com \
    --authorized \
    --format markdown

The Markdown report groups by severity; map each finding to the

PLAYBOOK.md snippet for the target server type. Observatory grade

typically moves D → B after addressing all HIGH findings.

Example 2 — HSTS preload eligibility pre-submission

User: "We want to submit to hstspreload.org. Is our HSTS config ready?"

python3 ${CLAUDE_PLUGIN_ROOT}/skills/checking-http-security-headers/scripts/check_headers.py \
    https://example.com \
    --authorized --min-severity low

Look for "HSTS max-age below preload threshold" and "includeSubDomains

missing" — both must clear before submission, OR hstspreload.org will

reject.

Example 3 — Authenticated-endpoint Cache-Control sweep

User: "We had a Cache-Control bug last quarter where authenticated

responses got cached publicly. Audit /api/* to make sure it's fixed."

python3 ${CLAUDE_PLUGIN_ROOT}/skills/checking-http-security-headers/scripts/check_headers.py \
    https://api.example.com/me \
    --authorized --authenticated

The --authenticated flag bumps Cache-Control posture from MEDIUM to

HIGH and adds a check for Cache-Control: public (forbidden on

authenticated content).

Output

JSON / JSONL / Markdown. Exit codes 0 / 1 / 2 per lib/report.py.

Error Handling

• No HTML response → INFO finding noting headers may not apply

(JSON APIs use a subset of headers).

• Redirect to login → follows once, audits the destination page.
• Connection error → exit 2.

Resources

• references/THEORY.md — Per-header reasoning, attack-class mapping
• references/PLAYBOOK.md — Config snippets per server type for each

required header

• ../analyzing-tls-config/references/AUTHORIZATION.md — Active-scan

authorization