Rooted. Getting user was fun, was able to use some things I learned from CTFs a while back. This box ended up being super simple for root, just have to do some typical Windows enumeration and pay attention to syntax once you find the interesting configuration (many hints in this thread already).
I was able to run various commands with what I thought was the right syntax, but any time I tried to t*** a specific file it ended up failing. After a simple syntax change, I was able to run the command with no issues.