Pentest Engagement

Pentest Engagement

Orchestrates a scoped pentest end-to-end via the pentest-engagement workflow. It is the breadth-complete, coverage-gated counterpart to the flag-shaped htb-solve — same engine (coordinator-loop, now with interleaved per-finding validation built into the loop), but driven by an attack-class coverage matrix instead of a flag, with surface expansion and root-cause severity baked in.

When to use

A real (non-CTF) engagement defined by a scope — either:

• WEB — web / API / cloud apps defined by apex domains / asset URLs, or
• NETWORK — a list of IPs / CIDRs / ranges (e.g. 1500 hosts) to scan for live services and vulnerabilities.

The workflow auto-detects the mode in Setup (engagement_kind): predominantly IPs/CIDRs → network; apex domains / app URLs → web. For HackTheBox/CTF use hackthebox (htb-solve) instead.

Run it

WEB — from a scope file or inline:

Workflow('pentest-engagement', { scope_file: 'projects/pentest/<engagement>-scope.md' })
Workflow('pentest-engagement', { scope: { engagement_name, apex_domains:[], assets:[...], creds_env:[...], roe, business_tier } })

NETWORK — inline IP/CIDR list or a scope file containing one (a plain newline list of IPs/CIDRs is accepted):

Workflow('pentest-engagement', { targets: ['10.0.0.0/24', '192.0.2.0/24', '198.51.100.7'] })
Workflow('pentest-engagement', { scope_file: 'projects/pentest/<engagement>-ips.txt', scan_profile: 'standard' })

Options (shared): maxConcurrent (default = prudent, derived from CPU cores — ~half the cores, capped 2–8; never hundreds/thousands of parallel tasks), dryRun, max_experiments, business_tier, report (default true). Options (network): scan_profile light (bounded 1-1024 + curated less-common, for large/fast sweeps) / standard (full-range -p- on every reachable host, DEFAULT; two-stage SYN→-sV on found-open ports, host-count-guarded, message-bus + non-443-TLS aware) / full (-p- + bounded UDP); udp (top-50 UDP; off for light/standard, auto-on for full); slice_size (hosts per scan worker, auto ≈64 IP-list / 2 CIDR-heavy); deepen_top (deep-dive the N highest-value hosts, default 10, 0 to skip); geo_vantages (≤2 gcp zones for the 2nd-vantage allowlist re-probe; overrides the US+EU default), auto_provision (default true; false = detect+flag only, no cloud spend). On a source-IP/geo-allowlist signature the workflow auto-provisions a 2nd-geography vantage and re-probes the filtered hosts before concluding "no surface."

Write the scope file per reference/scope-file-format.md. Credentials are referenced by env-var name only and read from the repo .env via python3 tools/env-reader.py — never inline secret values.

Phases (what the workflow does)

1. Setup — env-reader creds, parse scope, classify kind (web|network), read CPU cores → prudent parallel-task cap, OUTPUT_DIR = projects/pentest/<date>_<engagement>/, STARTED Slack (gated).
2. Expand (WEB, the #1 fix) — MANDATORY CT-log / passive-DNS / origin-discovery across every in-scope apex (crt.sh, certspotter, subfinder, origin-discovery for CDN/WAF-fronted hosts). Scope = the discovered surface, not the handoff. Builds the per-asset work list + seeds each asset's coverage matrix. Scan (NETWORK, replaces Expand) — slice the IP/CIDR set into machine-prudent batches; one nmap worker per slice (agents scale with slices ≈ dozens, never with IP count) runs the SAME pipeline: host discovery (reachability is unknown) → bounded common+less-common port/service scan → CVE surfacing (nmap --script vulners, nuclei, each CVE-ID enriched via tools/nvd-lookup.py) → writes a uniform per-IP tree hosts/<ip>/{recon,host.json,findings} + a merged recon/inventory/.
3. Assess (single interleaved stage — no separate downstream validation pass) — WEB: each asset → coordinator-loop (coverage mode), which validates each candidate the instant it is materialized on fresh blind agents (strict per-finding cure/drop loop) before search continues. NETWORK: bounded coordinator-loop deep-dives on only the deepen_top highest-value hosts, same interleaved per-finding validation (everything else is the uniform tool-scan, not a per-host agent). Coverage-by-VALID: a class is covered only by a VALID/REPAIRED finding, a justified N/A, or a genuine negative — a class whose candidates were all rejected/dropped stays pending and search keeps going.
4. Correlate — attack-path-stitcher + risk-prioritiser across all validated findings → ranked org roadmap.
5. Report (deterministic — no agent authors the report) — JS hands the resolved engagement block + exact commands to ONE finalize runner: tools/report_data_build.py merges the namespaced interim finding-JSONs into the canonical report_data.json (the sole-owner assembly), then the format-dispatched renderer runs — transilience → the canonical generate_report.py PDF skill, custom → custom_report_cmd (or a Markdown fallback). JS then hard-gates: report_data assembled ∧ (transilience: WROTE ∧ bytes>0 ∧ the [assets: …/formats/transilience-report-style] provenance tag), retry-once → BLOCKED. Only VALID/REPAIRED findings appear (drop-entirely — validated/ is confirmed-only by construction); REJECTED (false-positives/) and uncured DROPPED (dropped/) never appear and there is no gaps/assurance section. The finalize runner also runs network_coverage_map.py (swept-host tail) + coverage_gate.py over the whole engagement, writes reports/coverage-matrix.json, and the deliverable includes a deterministic Attack Pattern Coverage section (surface-unit × attack-class). COMPLETE is a hard 100% gate: it requires the report to assemble+render AND the coverage gate to report complete:true (every applicable cell covered) — for BOTH web and network (network additionally requires scan-completion). Any untested applicable cell → INCOMPLETE_coverage / BLOCKED.
6. Package & deliver — a verified <report_id>_deliverable.zip (reports/ input/ logs/ artifacts/), a short stats summary (summary.md: agents, findings by severity, elapsed; tokens/cost render unavailable — no runtime token counter), and the workflow returns slack_offer: true.

Post-run (main loop, outside the workflow): because coordinators must not call AskUserQuestion, the invoking agent shows the returned summary and asks whether to post the deliverable_zip to Slack; on yes, python3 tools/slack-send.py --channel "$PENTEST_SLACK_CHANNEL_ID" (gated on a successful, COMPLETE engagement).

Report options: report_format transilience (default) | custom; custom_report_cmd (the custom renderer, receives the report_data.json path + reports/ dir); prior_report (a prior PDF or report_data.json — its title/sector/scope are metadata-only, never seeding the work list) + version to mint the cover version + "Supersedes" line.

Determinism (be honest)

The decision layer is a frozen pure-JS computeVerdict (parity-guarded, fixture-pinned), its operands are frozen per engagement via NVD/KEV --cache-dir snapshots (artifacts/nvd-cache/, artifacts/kev-snapshot.json), and the adversarial quorum is raised to 3. Given identical inputs the verdict is provably identical. But a fresh live run is highly reproducible, not 100% — LLM sampling produces the booleans/numbers that feed the verdict, and live-target drift moves the inputs; that ceiling is inherent and stated plainly, not papered over. Byte-identical results are a guarantee 100% only on replay of a frozen evidence set (the Phase-2 replay cache, artifacts/validation-cache/) — that is the sole context in which "same request → same result" is a guarantee rather than a strong tendency.

Boundaries

• Orchestrator only — never run the coordinator loop inline; the coverage/bookkeeping discipline needs the workflow boundary.
• A missing credential is not a global block — the unauthenticated surface is always tested; only a no-reachable-asset scope blocks.
• Reversible own-org/own-tenant writes are authorized by default (create-then-delete is non-destructive); destructive ops, DoS, brute force, and out-of-scope tenants are prohibited (set in RoE).

References

• scope-file-format.md — scope file schema + worked example
• coverage-matrix.md — the canonical attack-class coverage contract (completion gate)
• principles.md — scope-is-the-surface, reversible active exploitation, real-tools-first, root-cause severity
• pentest-report.md — Transilience report structure + §7.1 root-cause severity
• validator-role.md — engagement-validator attack-class coverage check (8)