Confirming pentest authorization

Confirming Pentest Authorization

Overview

Penetration testing is computer access. Without explicit authorization from the owner of the system under test, that access is a crime — Computer Fraud and Abuse Act in the US, Computer Misuse Act in the UK, equivalent laws everywhere else. The line between an authorized pentester and an unauthorized attacker is one signature on one document.

The penetration-tester pack's other skills (TLS analysis, CORS audit, dependency CVE scan, etc.) all assume that line has been crossed correctly. This skill is the first gate the orchestrator routes to. It refuses to declare an engagement authorized until a Rules of Engagement (ROE) attestation file exists, is signed, and contains the fields any real-world legal review will look for.

This is not paranoia or paperwork theater. Engagements DO go sideways: scope creeps mid-test, a tester probes an out-of-scope adjacent system, an SOC team escalates a "real" attack to legal, and the question "show us the ROE" comes up. If the ROE is in order, the answer is "here it is." If not, the conversation gets expensive fast.

When the skill produces findings

Finding	Severity	Threshold	Affected control
ROE file missing	CRITICAL	No attestation file at the expected path	(legal)
Required field missing	CRITICAL	authorizer, in_scope_targets, time_window, emergency_contact, or signature absent	(legal)
Signature missing	CRITICAL	No signature_block in ROE	(legal)
Signer not in allowlist	CRITICAL	signer email/key id not in .allowed-authorizers	(legal)
Time window expired	HIGH	current time outside time_window.start / time_window.end	(legal)
Time window not yet active	HIGH	current time before time_window.start	(legal)
In-scope target list empty	HIGH	in_scope_targets field present but empty	(legal)
Out-of-scope override (manual flag)	MEDIUM	tester requests a target not in the in-scope list	(legal)
Stale ROE (>30 days from sign date)	MEDIUM	last_signed_at older than 30 days; suggests refresh	(operational)
ROE present + signed + in window	INFO	All gates pass; engagement is authorized	(positive confirmation)

Prerequisites

• Python 3.9+
• ROE attestation file at ./roe.yaml (or pass --roe FILE).
• Optional .allowed-authorizers file listing email addresses or GPG key fingerprints permitted to sign ROEs.

ROE attestation file schema

engagement_id: ACME-2026-Q2-PENTEST-001
authorizer:
  name: Jane Doe
  email: [email protected]
  role: CISO
  organization: ACME Corp
in_scope_targets:
  - host: app.acme.example
    notes: production web app, full-stack pentest authorized
  - host: api.acme.example
  - cidr: 10.50.0.0/16
    notes: internal corporate range
out_of_scope_targets:
  - host: payments.acme.example
    reason: PCI scope, separate authz required
  - cidr: 10.99.0.0/16
    reason: production database tier, separate authz required
time_window:
  start: 2026-06-01T00:00:00Z
  end: 2026-06-30T23:59:59Z
emergency_contact:
  name: SOC On-Call
  phone: "+1-555-555-5555"
  email: [email protected]
rules:
  - No exploitation of confirmed findings without written prompt approval
  - No password cracking against production accounts
  - All testing pauses on declared business-hours blackouts
signature_block:
  signer: [email protected]
  signed_at: 2026-05-30T14:22:00Z
  signature: |
    -----BEGIN PGP SIGNATURE-----
    ...
    -----END PGP SIGNATURE-----

Instructions

Step 1 — Locate the ROE

The skill looks for ./roe.yaml by default. Override with --roe FILE. The ROE file should live with the engagement artifacts, NOT in the repo under test — typical layout is engagements/<client>-<date>/roe.yaml.

Step 2 — Run the verification

python3 ./scripts/check_authorization.py --roe engagements/acme-2026-q2/roe.yaml

Options:

Usage: check_authorization.py [OPTIONS]

Options:
  --roe FILE              Path to ROE attestation YAML (default: ./roe.yaml)
  --allowed FILE          Path to allowed-authorizers list (default: .allowed-authorizers)
  --check-target HOST     Verify HOST is in the in-scope list (repeatable)
  --output FILE           Write findings to FILE
  --format FMT            json | jsonl | markdown (default: markdown)
  --min-severity SEV      Default info

Step 3 — Interpret findings

CRITICAL = engagement is NOT authorized. Halt all testing immediately. Resolve the missing requirement before any further skill runs.

HIGH = the engagement was authorized at some point but the current state is out-of-window. Either extend the time window with a new signature or wait.

MEDIUM = operational concerns that warrant attention but don't block testing. A stale ROE should be refreshed; a manual out-of-scope target request needs explicit additional authz.

INFO = positive confirmation that the engagement is authorized.

Step 4 — Save the result

The skill's output IS the authorization record. Save the markdown report alongside the ROE itself; it becomes part of the engagement evidence chain (see recording-pentest-engagement for the storage pattern).

Examples

Example 1 — Pre-flight check before any scan

python3 ./scripts/check_authorization.py --roe engagements/acme-2026-q2/roe.yaml --format markdown
# If exit code != 0, halt testing.

Example 2 — Confirm a specific target is in-scope before probing

python3 ./scripts/check_authorization.py \
    --roe engagements/acme-2026-q2/roe.yaml \
    --check-target app.acme.example \
    --check-target api.acme.example

The skill returns an explicit INFO Finding per target if all checks pass, and a HIGH/CRITICAL Finding per target if any are out-of-scope.

Example 3 — Generate authorization evidence for the audit trail

python3 ./scripts/check_authorization.py --roe engagements/acme-2026-q2/roe.yaml \
    --format json \
    --output engagements/acme-2026-q2/evidence/authz-check-$(date +%Y%m%d).json

Output

JSON / JSONL / Markdown per lib/report.py. Exit codes: 0 clean, 1 high/critical (engagement NOT authorized), 2 error.

Each Finding includes:

• id — authz::<field> or authz::target::<target>
• severity — CRITICAL / HIGH / MEDIUM / INFO
• category — engagement-authorization
• summary — what's missing or wrong
• evidence — engagement_id, authorizer email, time window, target

Error Handling

• ROE file not found → emits a CRITICAL finding and exits 1.
• Unparseable YAML → emits a CRITICAL finding with the parser error and exits 2.
• Allowed-authorizers file missing → emits an INFO finding (allowlist is recommended but not required) and proceeds with field-level verification only.
• Signature block present but unparseable → emits a CRITICAL finding flagging the issue; does NOT attempt to verify cryptographically (separate gpg --verify step recommended for signature validation; this skill validates the structural presence and signer-identity claim).

Resources

• references/THEORY.md — Why pentest authorization is a legal primitive (CFAA, CMA, equivalent statutes), ROE structure history (OSSTMM / PTES origins), signature options (PGP / S/MIME / DocuSign), scope-creep failure modes
• references/PLAYBOOK.md — ROE templates per engagement type (external pentest, internal pentest, red team, purple team), authorization escalation flow, time-window extension procedures, emergency-stop protocol