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Hack The Box: Vintage Machine Walkthrough – Hard Difficulty

Recently completed an Active Directory penetration test where I obtained both the user and root flags through a series of Kerberos and privilege escalation attacks. I first exploited a weak password on a legacy computer account (fs01$) to retrieve a Kerberos TGT and extract the gMSA password. After reactivating a disabled service account (svc_sql), making it ASREPRoastable, and cracking its hash, I gained credentials for another domain user and authenticated via Evil-WinRM to capture the user flag. For the root flag, I decrypted DPAPI-protected secrets to access a higher-privileged account (c.neri_adm), added a compromised service account to a privileged group, assigned an SPN, and performed a Kerberos delegation attack to impersonate a domain admin, ultimately achieving SYSTEM-level access and capturing the root flag. Great experience applying Kerberos exploitation techniques and privilege escalation strategies in a real-world scenario!

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Hack The Box: Administrator Walkthrough Medium Difficulty

Chained privilege escalation on an AD environment via misconfigured permissions — no CVEs, just clever abuse of default rights. From Olivia to Emily to Ethan, we pivoted through user relationships using BloodHound, CrackMapExec, Kerberoasting, and WinRM access. Highlighting how overlooked configurations can lead to full domain compromise.

#ActiveDirectory #PrivilegeEscalation #BloodHound #Kerberoasting #HackTheBox #RedTeam #CyberSecurity #WindowsPentest

Hack The Box: Certified Machine Walkthrough – Medium Difficulty

Access is gained using Judith Mader’s credentials, allowing enumeration of network resources. CrackMapExec identifies key accounts like management_svc and ca_operator. Privilege escalation is performed using a Shadow Credentials attack with Certipy, taking control of management_svc. With valid credentials, Evil-WinRM establishes a remote session, leading to the user flag.

For root access, the attack exploits Active Directory Certificate Services by modifying ca_operator’s User Principal Name (UPN) to Administrator, enabling a privileged certificate request. A vulnerable ESC9 certificate is issued without linking back to ca_operator, effectively granting Administrator access. The UPN is restored to avoid detection, and authentication via Kerberos retrieves the NT hash of the Administrator account. Full system control is confirmed by obtaining the root flag.

#HackTheBox #Pentesting #ActiveDirectory #PrivilegeEscalation #CyberSecurity #EthicalHacking