Plex only providing insecure connections until I forced an HTTPS connection locally

So today my friend tried to access my Plex server using the Playstation app, unfortunately it said that my Plex server was un-reachable/offline but we could both access it via the web app or the mobile app.

So I did some googling and found a few threads on this (Plex not working on PS4) most of which said that changing the server to “insecure” mode, changing some settings in the Playstation app connecting and then turning “preferred” secure mode back on would do it.

Anyway I tried this, we turned on “insecure” mode, changed some settings in the Playstation app (see above thread for settings) and still no luck, so abandoning that attempt I tried to turn “preferred” secure mode back on, this is when everything wen’t wrong, suddenly we couldn’t access plex via the web app or our phones, I tried restarting the server no luck, I tried recreating the docker container the server was running in no luck, I even nuked all the cached data associated with Plex and re-indexed in an attempt to fix it no luck.

Finally when browsing the web app I realized that it wasn’t showing me the server because it couldn’t get a secure connection (despite using the “preferred” secure mode) when I allowed a “one off” insecure connection it all worked fine, so this was kind of progress.

Next up I tried accessing the server locally over HTTP, all worked as expected, now I tried accessing locally over HTTPS I got a certificate warning as expected added an exception and carried on this all seemed to work.

Then I re-opened the web app and suddenly my server has re-appeared and had a secure connection…???

So my question is, does plex only issue the certificate when an HTTPS connection is created, and if so do I need to hit the HTTPS version locally every time I toggle “insecure”/“preferred” security modes?

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