I have an "insecure connection"
Insecure connections troubleshooting

I do not have CDN enabled

Plex.tv handles dynamic assigning of SSL certificates for all servers, if you are getting an insecure connection, it is either because your client has issues connecting via SSL, or plex.tv has issues assigning you a certificate.
Try restarting the server
Try resetting config via manage page and re-claim
Wait it out

I have CDN enabled

Go to your dashboard, grab your shared ID and open https://{YOUR-SHARED-ID}.elysium.to in your browser, does it load? If so, secure connections work fine and you can conclude its a client issue
If it doesn't work, CDN may be broken - uninstall, and re-install