Just finished the Checkpoint machine on Hack The Box (Medium difficulty) and it was a really enjoyable Active Directory box with some modern and creative attack paths.

I started with the provided credentials for `alex.turner`. After some enumeration I discovered that a previously deleted account (`mark.davies`) could be restored and that this account had write access to a share called DevDrop. This share was used by the organisation to stage VS Code extensions.

By creating a malicious VSIX extension targeting VS Code engine version 1.118.0 and dropping it on the share, a scheduled task automatically installed the extension and gave me a reverse shell as `ryan.brooks`. This was a really clean example of abusing enterprise software deployment processes.

From the `ryan.brooks` foothold I used Rubeus to obtain a TGT, then leveraged bloodyAD to create a malicious dMSA under a writable OU and impersonated a higher-privileged account. This eventually granted access to a VMBackups share containing a Windows Server memory dump. Using Volatility I extracted the local Administrator NTLM hash from the dump, authenticated with Evil-WinRM, and captured the root flag.

Overall, Checkpoint does a great job of chaining together several current techniques: writable shares for extension abuse, deleted object restoration, dMSA abuse, and memory forensics. It’s a solid Medium box that feels realistic and rewards careful enumeration.

Would recommend it to anyone working on modern Windows / Active Directory attack paths.

#HackTheBox #CyberSecurity #PenetrationTesting #ActiveDirectory #RedTeam #HTB #InfoSec #WindowsSecurity #PrivilegeEscalation #Kerberos #MemoryForensics …

Learn MoreHack The Box: Checkpoint Machine Walkthrough Medium Difficulty

The post Hack The Box: Checkpoint Machine Walkthrough Medium Difficulty appeared first on Threatninja.net.

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

The post Hack The Box: Logging Machine Walkthrough – Medium Difficulty appeared first on Threatninja.net.