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7-phase master pentest pipeline covering the full lifecycle from passive reconnaissance to exploitation and reporting. Distilled from 100+ targets across government, healthtech, fintech, e-commerce, ISP, and SMB sectors. This is the "meta-playbook" — it tells you what to do at each stage of an engagement and which skills to load for each phase.
When to Use
Starting a new pentest engagement with an unknown target.
You need the canonical workflow for any type of target.
After surface recon — this playbook tells you what to do next.
Training — understand the full lifecycle of a professional pentest.
When brute force / direct attacks aren't producing results, DO NOT persist — pivot to lateral discovery. This is the single most important judgment call in a pentest.
Pivot Triggers — Know When to Switch Vectors
Signal
Current Vector
Pivot To
100+ passwords tested, zero hits
Brute force (login)
SSRF, CORS, subdomain enum, API discovery, source leak, open registration, Firebase/Supabase
All common creds fail on MySQL/SSH
Database/SSH brute
API discovery (port scan for HTTP services), JS bundle secrets, Firebase config, CORS exfil
WAF/403 on every payload
Web exploitation
CDN bypass (origin IP discovery), subdomain enum (staging/dev may lack WAF), API on non-standard ports, HTTP method/header tampering
Sister-app sweep — same IP / cert / headers → same vulnerable code template on other paths
The 3-Attempt Rule
Before spending more than 5 minutes on any SINGLE attack vector:
Try the primary approach (e.g., 100 pwds via multicall)
Try one lateral pivot (e.g., check open registration)
Try one creative alternative (e.g., check CORS, Firebase, JS secrets)
If none worked in 3 distinct attempts, the vector is low-probability. Document what was tried and move on. Do NOT cycle back to the same vector with more of the same — find a qualitatively different angle.
Anti-Pattern: The Brute Force Trap
"Let me just try 100 more passwords..."
"Maybe I need a bigger wordlist..."
"Let me try one more round..."
🚫 STOP. If the first 100 targeted passwords didn't work, the next 10,000 won't either (for real-world passwords). Instead:
Check if there's ANY authentication at all (CORS no-auth endpoints)
Check if registration is open (create your own account)
Check if the auth uses JWTs you can forge (alg=none, weak HMAC)
Check if there's a different auth path (SSO, OAuth, SAML)
Move on to a different target entirely
Pitfalls
Don't skip Phase 1. Many critical findings come from passive recon (source leaks, GitHub SA keys).
Don't spend more than 15 min on Phase 2. Quick filter is enough — save deep probing for Phase 6.
OPSEC is not optional. Use proxy-ns or proxychains + Tor from the start. Never burn your source IP.
.env is not always a finding. Verify content contains actual credentials (DB_, APP_KEY), not just SPA catch-all HTML.
Document as you go. Don't wait until Phase 7 — you'll forget exact commands.
Don't brute-force past the pivot trigger. 100 targeted passwords per vector is the max before lateralizing.
Verification
Each phase has a clear exit criterion (e.g., "score >= 6 → escalate to Phase 6").
Every finding must be reproducible with the exact command.
All findings must pass the 7-question gate before reporting.