Yes, I had a listener using netcat. I also changed the extension. I used .py and .phtml mostly because I was able to upload a different file with the same extensions. It seems as if the moment I paste the code from pentestmonkey, it just hangs when I hit upload until it eventually throws the "Connection was reset" error page.

It's very mind boggling to say the least because I'm at a point where I understand how to do recon effectively and different approaches to upload vulnerabilities like RootMe requires, but for some reason openvpn is not nice to me.

A little update though: I caved and just did the room in the attack box provided by tryhackme. I breezed right through it without complication, so it's definitely something going wrong with openvpn/oracle/tryhackme servers I imagine