CUPS is too hard

I’m desperately trying to retire a server i have. It’s sole remaining task is to share the attached printer on the network via Samba. It uses CUPS as the backend. Trying to print a test page gives No such file or directory. That’s nice, but it should at least say what the file or directory it cannot find actually is.

Trying to connect to the printer from a Windows machine (I can see the printer find in the server share) gives an error that it cannot connect, but nothing appears in the Samba or CUPS logs.

This is 2017, surely we have better diagnostics to solve these issues!