Asked a programmer our side (.net) who said it'd take a couple of hours to write a simple webserver, package it up into an .msi and give it us. I got annoyed, did it in Golang in about 10 lines of code.
I then realised i'd compiled a Linux executable on Linux, remembered it did cross-compiling, 10 seconds later I had a Windows .exe. All for a simple webserver that printed "cock", not useful but it proved the tunnels worked.
Sometimes we overcomplicate the simplest shit.
EDIT: As it wasn't clear (my fault) - we were trying to get to port 443 at their end - they were on Windows, we mainly Linux but the guys I asked were .net programmers..