I ended up getting through it, don’t know if it was a misconfiguration or not.
user: Rather than following the walkthrough or yeeting typical payloads to catch a shell, I downloaded a nice common networking tool onto the box and used that instead.
root: I might have needed a better quality shell, because even though I was able to elevate myself my new more powerful shell wasn’t able to be used properly. l ended up finding a different way to get the flag.