They were definitely both using HTTPS on port 443 with identical passwords.
The weird thing is that there were no errors indicating success or failure in the System Log. If it claimed bad password or can't connect, then I would have something to work with.
Instead, I'd make a change and nothing would happen.
Also strange was that it would work for a while after a reboot, so it wasn't completely non-functional, it just stopped working after a while? shrug