web-pentest

---
name: web-pentest
description: |
  Authorized web application penetration testing — reconnaissance, vulnerability
  analysis, proof-based exploitation, and professional reporting. Adapts
  Shannon's "No Exploit, No Report" methodology with hard guardrails for
  scope, authorization, and aux-client leakage. Active testing against running
  applications you own or have written authorization to test.
platforms: [linux, macos]
category: security
triggers:
  - "pentest [URL]"
  - "pentest this app"
  - "penetration test [URL]"
  - "security test this web app"
  - "test [URL] for vulnerabilities"
  - "find vulns in [URL]"
  - "OWASP test [URL]"
toolsets:
  - terminal
  - web
  - browser
  - file
  - delegation
---

# Web Application Penetration Testing

A phased pentesting workflow for running web applications. Adapted from
Shannon's pipeline (Keygraph, AGPL — concepts only, no code borrowed).
Built around three rules:

1. No exploit, no report — every finding requires reproducible evidence.
2. Bounded scope — every active request goes against a target the operator
   pre-declared. Off-scope hosts are refused.
3. Bypass exhaustion before false-positive dismissal — a "blocked" payload
   is not a clean bill of health until you've tried the bypass set.

---

## ⚠️ Hard Guardrails — Read Before Every Engagement

Violating any of these invalidates the engagement and may be illegal.

1. **Authorization gate.** Before the first active scan in a session, you
   MUST confirm with the user, in writing, that they own or have written
   authorization to test the target. Record the acknowledgement in
   `engagement/authorization.md` (see template). No acknowledgement → no
   active scanning. Reading public pages with `curl` is fine; sending
   payloads is not.

2. **Scope allowlist.** Maintain `engagement/scope.txt` — one hostname or
   CIDR per line. Every `nmap`, `curl`, `whatweb`, browser navigation, or
   payload-bearing request MUST be against an entry in scope. If a target
   redirects you off-scope (3xx to a different host, a link in HTML),
   STOP and confirm with the user before following.

3. **No production systems without paper.** If the user hasn't told you
   "yes, prod is in scope and I have written sign-off," assume not. Default
   targets are staging, local docker, dedicated test instances.

4. **Cloud metadata is off by default.** Do not probe `169.254.169.254`,
   `metadata.google.internal`, `100.100.100.200`, `[fd00:ec2::254]`, or
   equivalent unless the engagement explicitly includes SSRF-to-metadata
   as a goal AND the target is one you control. The agent's browser tool
   can reach these from inside your own infrastructure — don't.

5. **Destructive payloads need approval.** SQLi payloads that DROP/DELETE,
   filesystem-write SSTI, command injection with `rm`/`shutdown`/`mkfs`,
   anything that mutates beyond a single test row → ASK FIRST. The
   `approval.py` system catches some; don't rely on it alone.

6. **Aux-client leakage risk (Hermes-specific).** This skill produces
   sessions full of SQLi/XSS/RCE payloads, captured credentials, JWT
   tokens. Hermes' compression and title-generation paths replay history
   through the auxiliary client (often the main model). Anything sensitive
   you write to the conversation can leave the box on the next compress.
   Mitigation:
   - Redact captured tokens/credentials to the LAST 6 CHARS before logging
     them in any message. Full values go to `engagement/evidence/` files,
     never into chat history.
   - If the engagement is sensitive, set `auxiliary.title_generation.enabled: false`
     in `~/.hermes/config.yaml` for the session.

7. **Rate limit yourself.** Default 200ms between active requests against
   any single host. The recon-scan.sh script enforces this. Don't bypass
   it without operator approval.

8. **Authority of the report.** This skill produces a security
   assessment, not a "PASS." Even a clean run is "no exploitable issues
   FOUND in scope X within time T using methods Y" — not "the application
   is secure." Mirror that language in the report.

---

## Phase 0: Engagement Setup

Before any scanning happens, create the engagement directory and
authorization acknowledgement.

```bash
ENGAGEMENT=engagement-$(date +%Y%m%d-%H%M%S)
mkdir -p "$ENGAGEMENT"/{evidence,findings,reports}
cd "$ENGAGEMENT"
```

1. **Ask the user (verbatim):**
   > "Confirm: (a) the target URL is [X], (b) you own this application
   > or have written authorization to test it, and (c) the engagement
   > may run for up to [N] hours starting now. Reply 'authorized' to
   > proceed."

2. **Wait for explicit `authorized` response.** Any other answer means STOP.

3. **Record authorization** to `engagement/authorization.md` using the
   template in `templates/authorization.md`. Include:
   - Target URL(s) and IP(s)
   - Authorization basis (ownership / written authz from $name)
   - Engagement window
   - Out-of-scope items (production, third-party services, etc.)
   - Operator name (the user driving this session)

4. **Build scope.txt:**
   ```
   localhost
   127.0.0.1
   staging.example.com
   192.168.1.0/24    # internal lab only, with operator OK
   ```

5. **Read** `references/scope-enforcement.md` before issuing the first
   active request — that doc has the host-extraction rules you apply
   to every command/URL before it goes out.

---

## Phase 1: Pre-Recon (Code Analysis, optional)

Skip if no source access (black-box engagement).

If you have read access to the application source:

1. **Map the architecture** — framework, routing, middleware stack
2. **Inventory sinks** — every `execute(`, `os.system(`, `eval(`,
   template render, file read/write, redirect target
3. **Map auth** — session cookie vs JWT, OAuth flows, password reset,
   privileged endpoints
4. **Identify trust boundaries** — what's authenticated, what's not,
   what comes from `request.*`
5. **Backward taint** from each sink to a request source. Early-terminate
   when proper sanitization is found (parameterized queries, allowlists,
   `shlex.quote`, well-known escapers).

Output: `evidence/pre-recon.md` — architecture map, sink inventory,
suspected vulnerable code paths.

This is OFFLINE work. No traffic to the target.

---

## Phase 2: Recon (Live, Read-Only)

Maps the attack surface. All requests are GETs of public pages, no
payloads yet. Still scope-bounded.

1. **Verify scope.** Resolve every target hostname → IP. Confirm IPs are
   in scope (avoids the "DNS points somewhere unexpected" trap).

2. **Network surface** (only if scope permits port scanning):
   ```bash
   nmap -sT -T3 --top-ports 100 -oN evidence/nmap.txt $TARGET
   ```
   Use `-T3` (default), not `-T4/-T5`. Stealthier and avoids tripping
   IDS/IPS in shared environments.

3. **Tech fingerprint:**
   ```bash
   whatweb -v $TARGET_URL > evidence/whatweb.txt
   curl -sIk $TARGET_URL > evidence/headers.txt
   ```

4. **Endpoint discovery:**
   - Crawl the app with the browser tool (`browser_navigate`,
     `browser_get_images`, follow links).
   - Inspect `robots.txt`, `sitemap.xml`, `.well-known/*`.
   - Use the developer tools network panel via browser tool to capture
     XHR/fetch calls.

5. **Auth surface:** Identify login, registration, password reset,
   session cookie names, token formats. Do NOT send credentials yet —
   just observe.

6. **Correlate with pre-recon** (if you have source). For each
   `evidence/pre-recon.md` finding, mark whether the live surface
   confirms it's reachable.

Output: `evidence/recon.md` — endpoints, technologies, auth model,
input vectors.

---

## Phase 3: Vulnerability Analysis

One delegate_task per vulnerability class. Each agent reads
`evidence/recon.md` (+ `evidence/pre-recon.md` if present), produces
`findings/<class>-queue.json` using `templates/exploitation-queue.json`.

Use `delegate_task` with these focused subagents (parallel where possible):

| Class | Goal | Reference |
|-------|------|-----------|
| `injection` | SQLi, command, path traversal, SSTI, LFI/RFI, deserialization | `references/vuln-taxonomy.md` (slot types) |
| `xss` | Reflected, stored, DOM-based | `references/vuln-taxonomy.md` (render contexts) |
| `auth` | Login bypass, JWT confusion, session fixation, OAuth flaws | `references/exploitation-techniques.md` |
| `authz` | IDOR, vertical/horizontal escalation, business logic | `references/exploitation-techniques.md` |
| `ssrf` | Internal reachability, metadata, protocol smuggling | Skip metadata unless explicitly authorized |
| `infra` | Misconfig, info disclosure, default creds, exposed admin | `references/exploitation-techniques.md` |

Each queue entry has: id, vuln class, source (file:line if known),
endpoint, parameter, slot type, suspected defense, verdict
(`identified` / `partial` / `confirmed` / `critical`), witness payload,
confidence (0-1), notes.

The analysis phase doesn't send malicious payloads yet — it stages them.
The exploitation phase actually fires them.

---

## Phase 4: Exploitation (Proof-Based, Conditional)

Only run a sub-agent per class where the analysis queue has actionable
entries (`identified` or `partial`).

For each candidate:

1. **Pre-send check** — host in scope? auth gate satisfied? payload
   approved if destructive?
2. **Send the witness payload** — minimal proof. SQLi: `' AND 1=1--`
   then `' AND 1=2--`. XSS: a benign marker like
   `<svg/onload=console.log("HERMES-PENTEST-XSS")>`. Never `alert(1)` in
   stored XSS — it'll fire for other users in shared environments.
3. **Verify the witness fires** — for blind injection, use a sleep
   probe (`SLEEP(5)`) and time the response. For SSRF, use a
   tester-controlled callback host you own (NOT a public service like
   webhook.site for sensitive engagements — exfil paths).
4. **Promote level:**
   - **L1 Identified** — pattern matched, no behavior change
   - **L2 Partial** — sink reached, but defense in place
   - **L3 Confirmed** — payload changed app behavior in observable way
   - **L4 Critical** — data extracted, code executed, access escalated
5. **Bypass exhaustion before classifying as FP.** For each candidate
   that blocks: try at least the bypass set in
   `references/bypass-techniques.md` for that class. Only after the set
   is exhausted may you write `verdict: false_positive`.
6. **Record evidence** for every L3/L4:
   - Full request (method, URL, headers, body)
   - Response (status, headers, relevant body excerpt)
   - Reproducer command (curl one-liner)
   - Impact statement

Output: `findings/exploitation-evidence.md`

**Redact in evidence files:**
- Any captured credentials/tokens → last 6 chars only in chat;
  full value to `findings/secrets-vault.md` (gitignored).
- Other users' PII → redact.
- Your test credentials → fine to keep.

---

## Phase 5: Reporting

Generate the final report using `templates/pentest-report.md`. Sections:

1. Executive summary
2. Engagement scope (from `engagement/scope.txt`)
3. Authorization (from `engagement/authorization.md`)
4. Findings (L3/L4 only — proof-required). Per finding:
   - Title, severity (CVSS 3.1), CWE
   - Affected endpoint(s)
   - Proof (request + response excerpt)
   - Reproduction steps
   - Impact
   - Remediation
5. Not-exploited candidates (L1/L2 with notes on what blocked them)
6. Out-of-scope observations
7. Methodology / tools used
8. Limitations and what was NOT tested

**Severity policy:** CVSS only for L3/L4. L1/L2 are "candidates pending
verification" — don't assign CVSS to unverified findings.

---

## When to Stop

- The user revokes authorization.
- A candidate finding clearly impacts production data and you don't have
  approval for destructive testing — STOP and ask.
- The target starts returning 503/429 storms — back off, reconvene with
  the operator.
- You discover something *outside* the contracted scope (e.g. an exposed
  customer database while testing an unrelated endpoint). STOP, document,
  report to the operator. Do not pivot without explicit approval — that
  pivot is what makes pentesting illegal.

---

## What This Skill Does NOT Cover

- Network-layer pentesting beyond port scanning (no Metasploit,
  Cobalt Strike, AD attacks, network protocol fuzzing).
- Reverse engineering / binary analysis (see issue #383).
- Source-only static analysis (see issue #382).
- Active social engineering / phishing.
- Anything against systems the operator hasn't pre-authorized.

If the engagement needs any of these, escalate to a professional
pentester. This skill complements professional pentesting; it does
not replace it.

---

## Further Reading

- `references/scope-enforcement.md` — how to bound every active request
- `references/vuln-taxonomy.md` — slot types, render contexts, OWASP map
- `references/exploitation-techniques.md` — per-class payload patterns
- `references/bypass-techniques.md` — common WAF/filter bypasses
- `templates/authorization.md` — engagement authorization template
- `templates/pentest-report.md` — final report template
- `templates/exploitation-queue.json` — per-class finding queue schema
- `scripts/recon-scan.sh` — rate-limited nmap+whatweb+headers wrapper