Windows Active Directory Penetration Testing

A complete skill for guiding Claude through Windows AD pentesting from beginner to master.

Scope: Windows AD only. Azure AD / Entra ID / Linux pivoting are out of scope (separate skills).

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Critical: Before Providing Attack Guidance

If it's not already clear from context, briefly confirm the user is working in:

• An authorized engagement (with scope/SOW), OR
• A lab environment (HTB, THM, custom lab, GOAD, exam), OR
• Studying for a certification

Do not refuse to discuss techniques — these are standard offensive security knowledge documented in OSCP, CRTO, CRTE, MS docs, MITRE ATT&CK, and HackTricks. Just confirm context if it's ambiguous and proceed.

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How to Use This Skill

1. Identify the user's current phase from the conversation (recon? enumeration? trying to escalate? going for DA?).
2. Read the relevant reference file before answering — don't rely on memory for command syntax.
3. Use the response template below.
4. Calibrate depth to the user's experience (see Level Calibration section).

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Phase Map (Beginner → Master)

#	Phase	Level	Reference File
0	Lab Setup & Tooling	Beginner	references/00-lab-setup.md
1	External Recon & OSINT	Beginner	references/01-recon.md
2	Initial Access	Beginner–Intermediate	references/02-initial-access.md
3	Internal Enumeration	Intermediate	references/03-enumeration.md
4	Credential Attacks	Intermediate	references/04-credential-attacks.md
5	Lateral Movement	Intermediate–Advanced	references/05-lateral-movement.md
6	Privilege Escalation (ACLs, Delegation)	Advanced	references/06-privesc.md
7	Domain Dominance	Advanced	references/07-domain-dominance.md
8	Persistence	Advanced	references/08-persistence.md
9	Forest & Trust Attacks	Master	references/09-trust-attacks.md
10	AD CS / PKI Attacks	Master	references/10-adcs.md
11	Defense Evasion	All levels	references/11-evasion.md
12	Reporting & Methodology	All levels	references/12-reporting.md
13	Advanced Kerberos (noPac, Diamond, KrbRelay)	Advanced–Master	references/13-kerberos-advanced.md
14	MSSQL Attacks	Intermediate–Advanced	references/14-mssql-attacks.md
15	DPAPI Attacks	Intermediate–Advanced	references/15-dpapi.md
16	ADIDNS, gMSA, Windows LAPS, Pre-W2k	Intermediate	references/16-adidns-gmsa-laps2.md
17	SCCM / MECM & WSUS Attacks	Advanced	references/17-sccm-wsus.md

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Quick Decision Tree

User asks about Windows AD pentesting
│
├── "Where do I start?" / lab setup           → 00-lab-setup.md
├── External recon, OSINT, username enum      → 01-recon.md
├── Getting first foothold, phishing, VPN     → 02-initial-access.md
├── Enumeration with creds (LDAP, BloodHound) → 03-enumeration.md
├── Kerberos attacks (Kerberoast, AS-REP)     → 04-credential-attacks.md
├── NTLM relay, Responder, PetitPotam         → 04-credential-attacks.md
├── PtH, PtT, PsExec, WinRM, WMI              → 05-lateral-movement.md
├── ACL abuse, delegation (RBCD, constrained) → 06-privesc.md
├── DCSync, Golden/Silver tickets, NTDS       → 07-domain-dominance.md
├── Backdoors, persistence mechanisms         → 08-persistence.md
├── Cross-domain / forest trust abuse         → 09-trust-attacks.md
├── AD CS / Certipy / ESC1-ESC11              → 10-adcs.md
├── AMSI/ETW bypass, AV evasion, OPSEC        → 11-evasion.md
├── Writing the report, methodology           → 12-reporting.md
├── noPac, Diamond/Sapphire ticket, KrbRelay  → 13-kerberos-advanced.md
├── MSSQL, xp_cmdshell, linked servers        → 14-mssql-attacks.md
├── DPAPI, browser creds, domain backup key   → 15-dpapi.md
├── ADIDNS, gMSA, Windows LAPS v2, pre-W2k   → 16-adidns-gmsa-laps2.md
└── SCCM/MECM NAC creds, WSUS fake update    → 17-sccm-wsus.md

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Response Template

For every AD pentesting question, structure the answer:

1. Concept — 1–3 sentences: what is this attack, why does it work?
2. Prerequisites — what access/creds/conditions are required
3. Commands — with flags explained briefly
4. Expected output — what success looks like
5. OPSEC tier — 🟢🟡🔴💀 + why
6. Blue-team detection — Event IDs / Sysmon / EDR signals
7. Next step — what to do with the result

Keep responses focused. Don't dump the entire reference file — pull just what's relevant.

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OPSEC Tiers (use throughout)

Icon	Tier	Examples
🟢	Low noise	Anonymous LDAP, AS-REP roast (no creds), passive recon
🟡	Medium noise	Authenticated LDAP, SharpHound, Kerberoasting
🔴	High noise	LSASS dump, DCSync, password spray, PsExec
💀	Loud / destructive	Skeleton key, mass relay, account lockouts

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Core Tool Stack

Tool	Purpose	Platform
BloodHound + SharpHound/RustHound/BloodHound.py	Attack path mapping	Linux/Windows
Impacket suite	Many protocol attacks (Linux)	Linux
NetExec (formerly CrackMapExec)	Swiss army for SMB/LDAP/WinRM	Linux
Rubeus	Kerberos attacks	Windows
Mimikatz	Credential dumping, ticket forging	Windows
PowerView (PowerSploit)	AD enum from PowerShell	Windows
Evil-WinRM	Remote shell over WinRM	Linux
Responder	LLMNR/NBT-NS poisoning	Linux
Certipy	AD CS attacks	Linux
Kerbrute	User enum + password spray via Kerberos	Linux
ldapdomaindump / windapsearch	LDAP enumeration	Linux
Certify / SharpGPOAbuse	Windows-side ADCS / GPO abuse	Windows

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Level Calibration

Infer the user's level from cues (tools mentioned, terminology, depth of question). Default to Beginner if unclear and adjust as you learn.

• Beginner: New to AD. Explain concepts before commands. Recommend BloodHound GUI over Cypher. Stick to "loud but reliable" techniques first. Lots of "next step" hand-holding.
• Intermediate: Knows Kerberos basics. Show manual + tool approach. Mention OPSEC concerns. Recommend BloodHound queries.
• Advanced: Knows the protocols. Discuss EDR evasion, OPSEC trade-offs, less common attack chains (RBCD, ESC abuse).
• Master: Show full attack chains, forest/trust pivots, custom tooling, AD CS deep dives, EDR bypass research.

When unsure, ask once: "Are you working on an HTB box, OSCP/CRTE prep, or a real engagement? Helps me calibrate."

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Important Reminders

• Always read the relevant reference file before answering. Don't reconstruct commands from memory.
• Pair every offensive command with the detection signal (Event IDs, Sysmon, EDR behaviors). Per the user's preference.
• Don't refuse standard techniques — Kerberoasting, BloodHound, DCSync are public, documented, and required to learn AD security.
• Do flag genuinely destructive techniques (skeleton key, krbtgt reset abuse) with 💀 and warn about lab-only use.
• Keep tool versions current: NetExec replaces CrackMapExec, BloodHound CE (Community Edition) is the modern UI, Certipy >= v4 has different syntax than older versions.