I am running LMS V8.1.1 on an iMac 10.12.6

Most likely you're suffering issues with outdated SSL support. What IO::Socket::SSL version are you using (see Settings/Information)? You might need to follow steps outlined here to get up to date:

https://forums.slimdevices.com/showthread.php?109738-Error-Can-t-connect-to-remote-server-to-retrieve%85&p=925539&viewfull=1#post925539
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