Being box number 5 in the hack the box “starting point” introduction, it’s an easy machine. Initial recon shows that this is also, very obviously, a windows machine:

Let’s try to connect to it with xfreerdp /v:$target.

Password certainly expired. Interesting. Let’s try to open op a gui connection. The HTB pwnbox comes loaded with a program called Remmina, which is a great choice for things like RDP, VNC and other sort of connections which might require a gui.

Let’s connect. It asks for a username. The default username for any windows machine would be “Administrator” - and as it seems we can use that to succesfully establish a gui connection - without entering a password.

As you can see, the flag is right there on the desktop..

Explosion, done.

Remediation

  • Never ever run an Administrator account without password.
  • Do not expose an RDP connection to the internet directly. If you must:
    • Make sure you have a very secure password and a 2FA solution attached.
    • Make sure that the server is up to date and has a very short patch-cycle.
  • A better way to run RDP is to put it behind a network segment that requires a VPN connection to get in. That way there is already pre-established trust-trail to trace - and an audit trail if things should go sideways.