In a nutshell my problem started after years of no issues connecting to Plex Web / Apps, nothing changed and then suddenly remote access was no longer working and nothing could access the server.
I did my part by going through all support articles forums and several other additional trouble shooting steps. Long story short I basically did everything an experienced plex admin user could try etc. etc. and in the end I got halfway there. Now I got remote access working, but now plex web is not working unless connecting directly to server and when once I was able to use Required setting for secure connections I now have to use preferred in order to at least get the apps working / connected to server.
Attached is the logs which I downloaded after first doing a startup, then played a video on my AppleTV Plex app, Then tried to connect via app.plex.tv where I then got the issue.
Please help, I am a long time plex user / Lifetime Plex Pass subscriber and this by far is my worst issue with plex to date!
P.S. With my research I assume / hope it is a simple cert issue
Just a quick update. Yesterday remote shares to friends was not working, but today after testing it myself as well they are working again despite no changes on my end. So apps are working for both plex home users and regular friend shares, only plex web is not working still.
After confirming above status updated server to latest version - 1.28.1.6018. Confirmed no fixes or changes to issue same state as mentioned above.
Thanks for the help. After your reset I also decided to try a partial reset/rebuild of my server settings after your fix and went through settings setup again and now everything is working again and I can access via app.plex.tv and secure connections are working again.
I hope what we did fixed the issue, but just in case I attached new logs after everything is working again. Please look over to see if issue appears to be resolved. If not please advise where I should go to create a support request.