I believe this is the same author as Sumo.  The box states that it's "Beginner to Intermediate", the object is:  "Get the root shell i.e.(root@localhost:~#) and then obtain flag under /root)." and I'm glad I went back to read that because you don't need to elevate root to get the flag.  It also states:  "Warning: Be careful with "rabbit hole" -- not really sure exactly about that part.  Anyway, fun box so let's jump into it:

The description states that the box is "Beginner" and "Get the root shell i.e.(root@localhost:~#) and then obtain flag under /root)."  I don't want to put too much information up front but if you haven't been hacking for long, this is a blast from the past with a neat entry. 

We kick off with Nmap:

I got asked to build a PowerShell query to search the Windows Index.  Basically, the idea is that we could search for multiple files at once, with different extensions, and perhaps streamline the process over the GUI index search function.