SlipItIn/.agents/skills/security-specialist/steering/pentest.md

Penetration Testing

Active security assessment against a live target. Unlike code-only analysis, this involves running tools against actual systems — reconnaissance, scanning, exploitation attempts, and evidence collection.

When to use: The user has a target (domain, IP, web app URL) and wants an offensive assessment, not just source code review. This is the "attacker's perspective" workflow.

Prerequisites

• For localhost/dev targets: no authorization needed — it's the user's own machine.
• For remote/production targets: explicit written authorization from the target owner.
• Clear rules of engagement for remote targets (scope, testing window).
• Do NOT probe remote systems without confirmation.

Default Flow (Path + Dev)

When the user provides a codebase path without a remote URL:

1. Run SAST via steering/full-scan.md on the source code
2. Detect how to start the dev server:
   • Look for package.json → npm run dev / npm start
   • Look for docker-compose.yml → docker compose up -d
   • Look for Makefile → make run
   • Look for manage.py → python manage.py runserver
   • Ask the user if unclear
3. Start the dev server, wait for it to be ready
4. Run DAST against localhost:<port> (phases 2-4 below)
5. Correlate: match DAST findings to source code locations from SAST
6. Stop the dev server

Extended Flow (Path + Production URL)

When the user also provides a production URL:

1. Complete the default flow above (SAST + DAST localhost)
2. Show gate: "This will send active probes to [URL]. Authorized? [y/n]"
3. On confirmation: run DAST against production URL
4. Compare: findings present in dev but absent in prod (mitigated by infra?) and vice versa
5. Final report correlates all three layers

Phase 1: Reconnaissance

Gather information without touching the target directly, then move to active probing.

Passive (no direct contact with target)

python3 scripts/pentest.py recon-passive --target <domain>

The script runs:

• WHOIS lookup (registrar, nameservers, creation date)
• DNS enumeration (A, AAAA, MX, NS, TXT, CNAME records)
• Subdomain discovery via certificate transparency logs
• Technology fingerprinting from public sources

Active (direct contact — requires authorization)

python3 scripts/pentest.py recon-active --target <ip_or_domain> --ports <range>

The script wraps:

• Host discovery (ping sweep or TCP probe)
• Port scanning (top 1000 or full 65535 based on --ports)
• Service version detection on open ports
• OS fingerprinting

Record all discovered hosts, ports, and services. This becomes the attack surface map.

Phase 2: Enumeration

Dig deeper into discovered services.

Web targets

python3 scripts/pentest.py enumerate-web --url <base_url>

Covers:

• Directory and file brute-forcing (common paths, backup files, admin panels)
• Subdomain enumeration (DNS brute, certificate transparency)
• Technology stack detection (frameworks, CMS, WAF identification)
• robots.txt, sitemap.xml, .well-known paths
• HTTP method testing on discovered endpoints
• Authentication mechanism identification

Infrastructure targets

• Banner grabbing on non-HTTP services
• SMB share enumeration
• SNMP community string testing
• Default credential checks on known services

Phase 3: Vulnerability Identification

Map discovered services to known vulnerabilities and potential attack vectors.

Automated scanning

python3 scripts/pentest.py vuln-scan --target <url_or_ip> --type <web|infra>

For web targets, check OWASP Top 10:

1. Injection — SQLi, command injection, LDAP injection, template injection
2. Broken Auth — default creds, weak passwords, session fixation
3. Sensitive Data Exposure — cleartext transmission, backup files, source disclosure
4. XXE — XML entity injection in upload/API endpoints
5. Broken Access Control — IDOR, privilege escalation, path traversal
6. Misconfig — default pages, directory listing, verbose errors, CORS
7. XSS — reflected, stored, DOM-based
8. Insecure Deserialization — object injection in serialized data
9. Known CVEs — version-matched CVE checks against detected software
10. SSRF — server-side request forgery in URL parameters

Manual testing

After automated scans, test for logic flaws that scanners miss:

• Business logic bypasses (price manipulation, workflow skipping)
• Race conditions in state-changing operations
• Chained vulnerabilities (low-severity issues combining into high-impact)

Phase 4: Exploitation (Proof of Concept)

For each identified vulnerability, attempt controlled exploitation to confirm impact.

Rules:

• Minimal impact — demonstrate the bug, don't destroy data
• Document every step — screenshot, request/response, timestamp
• Stop if unexpected damage occurs
• Stay within authorized scope

Record results:

python3 scripts/scan_db.py add-finding \
  --scan-id <id> \
  --title "SQL Injection in /api/search" \
  --severity critical \
  --category injection \
  --file "api/routes/search.js" \
  --line 42 \
  --description "Unsanitized user input in search parameter passed directly to SQL query" \
  --evidence "Request: GET /api/search?q=1' OR 1=1-- Response: 200 OK with all database records"

Phase 5: Post-Exploitation (if in scope)

When rules of engagement allow:

• Lateral movement mapping (what else can you reach from compromised position)
• Privilege escalation attempts
• Data access assessment (what sensitive data is reachable)
• Persistence mechanism identification (not deployment — just identifying)

Phase 6: Reporting

python3 scripts/finalize.py --scan-dir .security

The pentest report adds to the standard report format:

Section	Content
Executive Summary	Business impact in non-technical language
Scope	Authorized targets, testing window, methodology
Attack Narrative	Chronological story of the assessment
Findings	Sorted by severity with full reproduction steps
Evidence	Screenshots, request/response dumps, tool output
Remediation	Prioritized fix recommendations with effort estimates
Positive Observations	What's working well (defenders need wins too)

Severity Rating

Follow references/severity-policy.md, but with CVSS alignment for pentest context:

Severity	CVSS Range	Pentest Context
Critical	9.0–10.0	RCE, full auth bypass, mass data exfil, supply chain
High	7.0–8.9	SQLi with data access, stored XSS + session theft, priv esc
Medium	4.0–6.9	Reflected XSS, info disclosure, missing security controls
Low	0.1–3.9	Missing headers, version disclosure, theoretical issues
Info	—	Best practices, hardening suggestions, architecture notes

Tools Reference

The scripts/pentest.py script wraps system tools when available and falls back to Python alternatives.

Tool Matrix

Function	System Tool	Python Alternative (pip)	Stdlib Fallback
Port scanning	nmap	python-nmap or python3-nmap	socket connect scan
DNS enumeration	dig, host	dnspython	socket.getaddrinfo
WHOIS lookup	whois	python-whois	crt.sh HTTPS query
Subdomain enum	subfinder, amass	bbot	crt.sh CT log query
Dir brute-force	gobuster, feroxbuster	dirsearch	urllib common-path check
Tech detection	whatweb, wappalyzer	builtwith, webtech	HTTP header analysis
Web vuln scan	nikto	wapiti3	Manual checks
Template scan	nuclei	wapiti3 (module-based)	Header/config checks
SQL injection	sqlmap	sqlmap (is Python)	Parameter probing
XSS detection	—	wapiti3, xsser	Reflected input check
OSINT recon	theHarvester	theHarvester (is Python)	Search API queries
HTTP proxy	burpsuite, mitmproxy	mitmproxy (is Python)	—

Installation

# Minimal (covers most use cases)
pip install dnspython python-whois requests

# Full pentest stack
pip install dnspython python-whois python3-nmap wapiti3 dirsearch bbot webtech mitmproxy

Priority Order

The script tries tools in this order:

1. System binary (fastest, most features) — e.g., nmap on PATH
2. Python pip package (portable, no root needed) — e.g., python3-nmap
3. Stdlib fallback (always works, limited) — e.g., socket scan

If nothing external is available, the stdlib fallback still produces useful results — just slower and less comprehensive.