Rules of Engagement (RoE) Generator

The RoE is the legally binding foundation of every red team engagement. All other documents build on it.

When to Use

• Starting a new engagement
• User says "create RoE", "define scope", "set boundaries"
• Before any other planning document can be created

Workflow

Step 1: Interview the User

Drive each dimension through one ask_user_question call (per CRITICAL_RULES #8 — every operator-facing question goes through the tool). Cover these roughly in order, never bundling multiple questions in one turn:

Identity & Scope

1. Engagement name (free-form, allow_other=true with sensible guesses)
2. Client organization (free-form, allow_other=true)
3. Engagement type — single-select: external / internal / hybrid / assumed-breach / physical
4. Start date / end date / testing window with timezone (free-form, allow_other=true — suggest defaults like "Mon-Fri 09:00-18:00 client TZ")
5. In-scope targets (free-form, allow_other=true — domains, IP ranges, cloud resources, applications)
6. Out-of-scope targets (free-form, allow_other=true)

Boundaries & Escalation 7. Additional prohibited actions beyond schema defaults (multi-select with sensible options + allow_other=true) 8. Special permitted actions — phishing, password spraying, raw-socket scans (multi-select) 9. Escalation contacts — minimum 2 (client + red team lead). One ask per contact slot covering name, role, channel 10. Authorization reference / contract # (free-form, allow_other=true)

Step 2: Generate plan/roe.json

Use the RoE schema from decepticon.core.schemas. Write to the engagement directory.

See references/roe-example.json for a complete example and ../references/schema-quick-reference.md for all required fields and valid values.

Step 3: Validate

Run through the checklist in references/validation-checklist.md before presenting to user.

Generation Rules

1. Always include default prohibited actions — DoS, unauthorized social engineering, unauthorized physical access, real data exfiltration, production data modification
2. Scope must be specific — CIDR notation for IPs, wildcard notation for domains
3. Testing window must include timezone
4. At least 2 escalation contacts required
5. Authorization reference must not be empty

Output

Write plan/roe.json to the engagement directory, then present a human-readable summary to the user for confirmation.