Multiple connection issues with FMS 16

[Cable]

I'm having multiple connection issues with FileMaker Server 16 running on a Windows 2016 VMWare server.

Background: I had my solutions running on a virtual server hosted with FMS 15. I started to have problems with overnight scripts not running and random slowness. My VMWare vendor suggested moving FileMaker to a new virtual server. I figured as long as I was moving I might as well upgrade to FMS 16. That process was completed yesterday. The old server was called Bloodgood and the new one is Bonsai.

I'm still having problems with my overnight scripts running and I think they're related to additional problems I'm having. I have a SSL certificate for the server. When I log into a database using FMPA 16 on the server, I get repeated errors that "the connection to fm.willowaynurseries.com:5003" is not encypted". I'll check off the box to always permit connection and hit the connect button and the lock will turn green. After a bit (seconds to minutes) the lock will turn orange and I'll get the connection message again. It is noteworthy that the SSL cert is ties to willowaynurseries.com and when the server was on Bloodgood if I tried to connect using the Remote button and let it find the local.Bloodgood server over the network I would get the connection error message but it didn't specify a port and once I told it to allow the connection I'd have no further problems.

Also, if I open one of the overnight scripts, it shows that same message but also shows that scripts referenced in other databases are "unknown" (see attached). As I scroll through the script it will also pop up an "open file" dialogue box, but won't tell me what file it is trying to open.

Even more oddly, none of this happens if I'm using FMPA 16 on my computer. Only if I use it on the server.

Does anybody have any idea what might be happening or how to troubleshoot/resolve?

[Cable]

Log viewer shows errors up the yin-yang...