Completed another Hack The Box machine: Hercules, an Insane difficulty Active Directory challenge.

This was one of the longer attack chains I have worked through, involving multiple stages across web exploitation, credential access, Active Directory enumeration, privilege escalation, AD CS, and Kerberos abuse.

The initial foothold started with LDAP username enumeration and the discovery of credentials stored in an account description. After gaining access to the Hercules Portal, a directory traversal vulnerability exposed the web.config file and its ASP.NET machineKey values. These values allowed a forged Forms Authentication cookie to impersonate web_admin.

From there, a malicious ODT upload triggered an outbound NTLM authentication attempt, allowing the NetNTLMv2 credentials for natalie.a to be captured and cracked. The recovered credentials opened the path to Shadow Credentials against bob.w and stephen.m, followed by OU permission abuse to gain control of the Auditor account.

The privilege escalation chain continued through the Forest Migration OU, where fernando.r was enabled and used to identify an ESC3 misconfiguration. An Enrollment Agent certificate was then obtained and abused to request a certificate for ashley.b, leading to further access within the domain.

The final stages involved controlling IIS_Administrator, taking control of the iis_webserver$ machine account, extracting the required Kerberos session key, and abusing S4U2self/S4U2proxy to impersonate Administrator. This ultimately provided access to the root flag under C:\Users\Admin\Desktop.

Hercules was a great exercise in chaining several seemingly separate weaknesses together rather than relying on a single vulnerability. Definitely a box that required careful enumeration and keeping track of the relationships between users, groups, OUs, certificates, and Kerberos tickets.

Documented as part of my continued HTB practice and learning in Active Directory and offensive security.

#HackTheBox #HTB #Hercules #CyberSecurity #ActiveDirectory #PenetrationTesting #RedTeam #OffensiveSecurity #BloodHound #Certipy #ADCS #ESC3 #Kerberos #ShadowCredentials #PrivilegeEscalation #InfoSec #CyberSecurityLearning …

Learn MoreHack The Box: Hercules Machine Walkthrough – Insane Diffucility

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Completed the Hack The Box “Pirate” machine, a hard-difficulty Active Directory challenge that required chaining multiple attack paths rather than relying on a single vulnerability.

The enumeration phase uncovered domain users, pre-created computer accounts, GMSAs, delegation relationships, and an exposed internal network. Access to gMSA_ADFS_prod$ led to DC01 and enabled an internal pivot to WEB01. From there, the attack chain involved GMSA credential retrieval, NTLM relay, authentication coercion, shadow credentials, certificate-based authentication, and Kerberos ticket abuse.

The privilege escalation path continued through constrained delegation and resource-based constrained delegation. Kerberos ticket manipulation ultimately provided Administrator access to the domain controller, followed by a SYSTEM-level shell and extraction of domain credentials from NTDS.dit. Both the user and root flags were successfully obtained.

Another challenging AD machine completed and another deep dive into Windows authentication, delegation, and privilege escalation.

#HackTheBox #HTB #CyberSecurity #PenetrationTesting #ActiveDirectory #RedTeam #Kerberos #NTLMRelay #ShadowCredentials #GMSA #PrivilegeEscalation #WindowsSecurity #Cybersecurity #Infosec #HTBWriteup …

Learn MoreHack The Box: Pirate Machine Walkthrough – Hard Difficulity

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Just wrapped up another Hack The Box machine: Fries (Hard).

TThis machine provided a realistic attack path that started with source code review in Gitea, where leaked credentials in a Git commit led to authenticated PostgreSQL RCE through pgAdmin. From there, I pivoted through the internal Docker network using Ligolo-ng, abused an exposed NFS share and debugfs to gain host access, then exploited PWM configuration weaknesses to capture LDAP credentials. The final stage involved Active Directory enumeration and AD CS (ESC6/ESC7) abuse to obtain an administrator certificate and compromise the domain. A great lab for practising web exploitation, Docker security, Linux privilege escalation, internal pivoting, and Active Directory attacks.

#HackTheBox #HTB #CyberSecurity #PenetrationTesting #RedTeam #ActiveDirectory #ADCS #Docker #Ligolo #PostgreSQL #Gitea #EthicalHacking #Writeup #CTF …

Learn MoreHack The Box: Fries Machine Walkthrough – Hard Difficulty

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Completed another Hack The Box machine focused on Active Directory exploitation and privilege escalation.

The attack involved SMB enumeration, credential discovery through log analysis, Kerberos authentication, Shadow Credentials abuse, and DLL hijacking to gain user-level access. Further enumeration revealed a WSUS infrastructure weakness, allowing exploitation through Kerberos delegation abuse, certificate-based authentication, and a WSUS machine-in-the-middle attack to achieve Domain Admin privileges. This challenge strengthened my understanding of modern AD attack paths, Kerberos abuse techniques, and enterprise infrastructure security.

#HackTheBox #HTB #CyberSecurity #ActiveDirectory #RedTeam #PenetrationTesting #OffensiveSecurity #EthicalHacking #InfoSec …

Learn MoreHack The Box: Logging Machine Walkthrough – Medium Difficulty

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