After several long days, I finally was able to pwn my first fortress on HackTheBox! Context by Context Information Security!
This particular challenge had seven flags and had me exploit my way through a vulnerable web app, into a Windows Domained machine and compromise several web and domain users in order to finally get Domain Admin and grab the final flag!
Without spoiling exact methodology, it was definitely a difficult challenge that required me to do a lot of extra research to help bolster my skills and help me breakthrough when I got stuck. I look forward to another challenge after I take a few days break from this one!