Hack The Box: Checkpoint Machine Walkthrough Medium Difficulty
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. Itβs a solid Medium box that feels realistic and rewards careful enumeration.
Would recommend it to anyone working on modern Windows / Active Directory attack paths.
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