Finally rooted. Thanks @egotisticalSW for creating this VM. This box was one of my first Windows boxes and it certainly wasn’t an easy VM for me. I learned a lot about the three-headed dog and AD.
User 1: Take a close look at the website, google AD user naming conventions and learn how to use that script that everyone keeps talking about.
User 2: Basic Windows priv esc methods are more than enough. Be thorough. I got stuck at this point for several hours because I skipped some tips and tricks I read about.
Root: Do some more enumeration on user accounts and google AD attacks. The hound is probably overkill for this machine. Learn about AD permissions and use your knowledge to feed the cats. The rest should be straightforward.