AI penetration-testing skills for Claude — web apps and networks.
Say the magic words, and the target opens up — the authorized way.
open-sesame is a suite of skills that turns Claude into a disciplined penetration
tester. Point it at a target you're authorized to assess and it runs the whole
engagement — maps the attack surface, works methodically through an industry
methodology, validates findings with the lightest safe proof, and writes clean reports
for both engineers and leadership.
| Skill | For | Methodology |
|---|---|---|
web-pentest |
A single web application / API | OWASP WSTG |
net-pentest |
Networks & infrastructure, incl. Active Directory | PTES / NIST SP 800-115 |
It's built as a set of Markdown instructions and small helper scripts — no model fine-tuning, no binaries. You can read every line of what it tells Claude to do.
Warning
Authorized testing only. This skill is for systems you own or have explicit permission to test (your own apps, a signed client engagement, an in-scope bug-bounty target, or a CTF / practice lab). It is designed to refuse unauthorized targets, treat the platform/host a target runs on as out of scope by default, and prefer non-destructive proofs. Using it against systems you don't have permission to test may be illegal. You are responsible for staying within scope and the law.
- Authorization-first — both skills confirm scope and rules of engagement before any active test, and treat third-party platform/cloud infrastructure as out of scope.
- Web (
web-pentest) — full OWASP WSTG coverage: recon, configuration, auth, session, access control (incl. multi-tenant isolation), injection, crypto, business logic, client-side, and API tests; safe RCE validation and reverse shells. - Network (
net-pentest) — PTES-based external and internal testing: host discovery, port/service scanning, enumeration, vuln ID, exploitation, privilege escalation (Linux + Windows), pivoting, and Active Directory attacks (Kerberoasting, BloodHound, NTLM relay, the path to Domain Admin) — plus hybrid/cloud identity (Entra ID, AWS), Wi-Fi, and container/Kubernetes testing. - Tooling playbooks — concrete, safe-usage workflows for Burp, ffuf, nuclei, sqlmap, nmap, masscan, netexec, impacket, responder, BloodHound, and more.
- Three reports, two audiences — a technical findings report, a plain-language stakeholder summary, and a how-to-recreate guide, each rendered to PDF.
Clone into a location Claude discovers skills from:
# Per project (available inside one repo) — installs both skills
git clone https://github.com/hassan-algo/open-sesame.git
cp -r open-sesame/.claude/skills/* .claude/skills/
# Or personal (available in every project)
cp -r open-sesame/.claude/skills/* ~/.claude/skills/In Claude Code, just describe the work — the right skill triggers automatically:
Pentest my web app at https://staging.myapp.example — I own it. Start with recon.
Scan my network 10.0.0.0/24 and enumerate Active Directory — it's my lab.
web-pentest triggers on things like "find vulns in my web app", "test for IDOR/SQLi",
"validate this RCE"; net-pentest on "scan this subnet", "enumerate these hosts",
"Kerberoasting / BloodHound", "privilege escalation on this box". Or invoke explicitly
with /web-pentest or /net-pentest.
After a report is drafted in Markdown, render it to a styled PDF:
# each skill ships the same renderer
.claude/skills/web-pentest/scripts/render-report.sh report.md report.pdfThe script converts Markdown → HTML (pandoc, else npx marked) → PDF (headless
Chrome/Chromium, else weasyprint, else macOS cupsfilter). Install at least one tool
from each stage.
.claude/skills/
├── web-pentest/ # single web application (OWASP WSTG)
│ ├── SKILL.md # authorization, workflow, pointers
│ ├── references/ # methodology, tooling, post-exploitation,
│ │ # reporting, lab-targets
│ ├── assets/report-template.md
│ ├── scripts/render-report.sh
│ └── evals/ # test cases + benchmarks
└── net-pentest/ # networks & Active Directory (PTES / NIST)
├── SKILL.md
├── references/ # methodology, active-directory, privesc,
│ # pivoting, password-attacks, cloud-identity,
│ # wireless, containers, tooling, reporting,
│ # lab-targets
├── assets/report-template.md
├── scripts/render-report.sh
└── evals/evals.json # trigger/behavior test cases
Supporting folders at the repo root:
index.html— the project landing page.reports/— generated engagement reports. Keep them local:reports/is not yet in.gitignore, so add it before committing.
Each skill uses progressive disclosure: SKILL.md is always loaded; the references/
files are pulled in only when a phase needs them, keeping the context lean and the
workflow fast.
web-pentest was built and tuned with Anthropic's skill-creator and validated across
two eval iterations — methodology, reporting, authorization-gating, RCE/reverse-shell
guidance, cross-tenant IDOR, and scope discipline. Summary results live in
.claude/skills/web-pentest/evals/benchmarks/.
Beyond the evals, see BENCHMARKS.md for timed, end-to-end
engagements, and CASE-STUDY.md for the story behind each one:
| Target | Skill | Objective | Active | Total (incl. PDFs) |
|---|---|---|---|---|
| Metasploitable2 (Docker) | web-pentest + net-pentest |
Root | ≈ 3 min | ≈ 6 min |
| Samba AD lab | net-pentest |
Domain Admin | ≈ 14 min | ≈ 17 min |
| OWASP Juice Shop (Docker) | web-pentest |
Admin + customer data | ≈ 2.5 min | ≈ 5 min |
Dead ends and lab-injected findings are documented, not hidden.
Contributions are very welcome — this gets better the more practitioners shape it. Good first contributions:
- Extend the methodology — add or sharpen WSTG test cases in
references/methodology.md. - Add tooling recipes — real-world command workflows in
references/tooling.md. - Improve reporting — templates, severity guidance, or the
render-report.shbackends. - Add eval cases — new prompts in
evals/that catch gaps or regressions.
See CONTRIBUTING.md for how to propose changes. Please keep everything aligned with the skill's core principle: authorized, non-destructive, methodical testing — contributions that add offensive capability without that framing won't be merged.
MIT — free to use, modify, and share.
- Methodology based on the OWASP Web Security Testing Guide & Top 10, the PTES, NIST SP 800-115, and MITRE ATT&CK.
- Built as Claude Agent Skills.