Secure Connections not working - running on 1.14.0.5468

There was a recently seen issue to do with issue of security certificates - server logs would show if it was this

run with debug logging enabled
See https://support.plex.tv/articles/201643703-reporting-issues-with-plex-media-server/

restart the server so we can see in the logs how the certificate is setup

check out if secure connections are working
if not get the logs from the server
See https://support.plex.tv/articles/200250417-plex-media-server-log-files/