Hi @DiBarkis,
If you haven’t done so already, send a ticket to zendesk with that first image you posted when you started this topic.
Asobo should correct that display when a timeout is happening. This has happened to other members as well and if my memory serves me correctly, this has happened prior to release of MSFS.
I’m not sure how the code works when a connection to a server is unreachable or fails to connect, but in theory, it should try another server.
Most important is submitting the zendesk ticket; same for others who have this issue.