OSCP · Module 17
Active Directory Authentication Attacks
Password spraying, Kerberoasting, AS-REP Roasting, NTLM relay, ADCS abuse, delegation exploitation, and ACL-based privilege escalation.
~5 h 29 resources Last updated September 27, 2026
Active Directory authentication relies on Kerberos, NTLM, and certificates. Each mechanism has exploitable weaknesses. PEN-200 covers password spraying, Kerberoasting, AS-REP Roasting, NTLM relay, ADCS abuse, delegation exploitation, and ACL-based privilege escalation. These attacks turn a single domain account into Domain Admin credentials.
Password and Credential Attacks
Password spraying uses the password policy (from Module 17 enumeration) to try common passwords across all domain accounts without triggering lockouts. Responder and Inveigh capture NTLMv2 hashes from the network for offline cracking. Once you have credentials, ForceChangePassword on vulnerable accounts, gMSA password extraction, and LAPS reads expand access further. DCSync with replication rights dumps every hash in the domain.
Kerberos and Certificate Exploitation
Kerberoasting requests service tickets for SPN-bearing accounts and cracks them offline. AS-REP Roasting targets accounts without pre-authentication. Delegation misconfigurations (unconstrained, constrained, RBCD) allow ticket forging for privileged services. ADCS misconfigurations (ESC1 through ESC10+) let you request certificates that authenticate as any domain user. Coercion attacks (PetitPotam, PrinterBug) force machine authentication for relay or delegation capture.
NTLM Relay and Privilege Escalation
NTLM relay forwards captured authentication to targets where signing is not enforced: SMB for command execution, LDAP for RBCD setup, or ADCS for certificate requests. ACL abuse (GenericAll, WriteDACL, WriteOwner) grants yourself privileges on domain objects. Shadow credentials, GPO abuse, privileged group membership, and sAMAccountName spoofing (noPac) provide additional escalation paths to Domain Admin.
Read
The core material for this module. Where a guide goes deeper than needed, the relevant sections are highlighted.
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Guide 3 min readPassword Spraying
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Guide 4 min readKerberoasting
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Guide 4 min readESC8 — NTLM Relay to AD CS Web Enrollment
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Guide 3 min readNTLM Relay Conditions
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Guide 5 min readShadow Credentials
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Guide 4 min readNoPac: sAMAccountName Spoofing
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Guide 3 min readGPO Abuse
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Guide 4 min readPrivileged Group Abuse
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Guide 4 min readDCSync and Domain Takeover
Practice
Apply the module hands-on.
- Active HackTheBox Easy
- Corp TryHackMe Easy
- EscapeTwo HackTheBox Easy
- Sauna HackTheBox Easy
- Support HackTheBox Easy
- Access Proving Grounds Intermediate
- Administrator HackTheBox Medium
- Authority HackTheBox Medium
- Intelligence HackTheBox Medium
- Manager HackTheBox Medium
- Querier HackTheBox Medium
- StreamIO HackTheBox Medium
- Blackfield HackTheBox Hard
- Flight HackTheBox Hard
- Mantis HackTheBox Hard
- Search HackTheBox Hard
- APT HackTheBox Insane
- Multimaster HackTheBox Insane
- Sizzle HackTheBox Insane