Thank you for your post!
Windows Server 2012 DataCenter is not a tested Operating System. You might see System Requirements for FileMaker Server 15. However, it may work just fine and the OS Upgrade shouldn't be necessary. Mainly, you want to verify the two machines are able to communicate. For Ports used by FileMaker Server, see Ports used by FileMaker Server.
I hope this helps!
This is a data center environment, I don't have the luxury of using Windows 2012 R2 Standard.
All the needed ports were checked and are open. (remember this worked fine under FMS14)
I also tried turning off all firewalls that had no effect.
Do you know if it is possible to connect FMS15 Master/Worker pair with a mix of 2008 R2 and 2012 R2 operating systems? (apparently I can't do it!)
Correct, you should be able to connect a Master/Worker between 2008 R2 and 2012 R2. All I can see from your screenshot is that it is unable to see or connect to the WebServer. I've not ran into this for any reason other than communication issues. I know this was working for you previously, but have you tried to ping 80/443 between the two machines?
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After some more digging, I looked at the Server Manager.
There were some errors there, I then discovered that the OS updater changed the permissions of the Log Folders. Since the OS couldn't write to the log's all sorts of things couldn't happen
Once we fixed the permissions issue, I was able to connect the Worker to the Master.
Thanks for your suggestions! This is solved, not FileMakers issue