[SOLVED] Possible Stuck plex.direct certificate

Plex Media Server Remote Access
1

Server Version#: 1.43.2.10687
Server Identifier: bf8f5251328a92ab714207b3bf0fc949f1a2a61b
Player Version#: (Irrelevant for this issue) 1.112.0.359-0d79a49f

I’ve recently migrated my Plex server from a Docker host to MacOS Native. However, after migrating I’ve been having issues getting remote access to work correctly. I suspect (after some forum reading) that I may have a stuck plex.direct LetsEncrypt certificate. Just wondering if anyone else has had a similar issue, or knows how to reset the certificate.

Some devices (both on LAN & WAN) are able to connect to the server fine, without any issues. But others will say the server is offline via the Plex app (notably most devices running an Android-based operating system.) In my PMS Settings via the Web App/Desktop Client, the server reports back that it is inaccessible from the internet. Even though I have checked and verified that the port fowarding is working (the Plex Media Server WebUI is accessible when navigating to http://[MY-WAN-IP]:32400. port forwarding has always worked for me in the past, both on the old Plex Media Server, as well for other connections, and continues to do so.

What I’ve tried:

  • Restarting PMS & it’s host.
  • Ensuring the server and PMS are fully up-to-date
  • Ensuring Host Firewall rules are not interfering with inbound/outbound connections (both on port 32400 & other documented discovery/function ports)
  • Ensuring DPI and Threat Protection are not interfering with any WAN connections to/from the PMS Host from my Router
  • Testing connections to the server, from both LAN & WAN (LTE) using both IP addresses and the plex.direct domain assigned to my server for remote access (though, when accessing via the plex.direct address with https I’m not currently getting an Invalid Certificate warning in the browser)
  • Verified via Router Firewall that traffic is reaching the PMS Host when attempting to connect via the app (when app states server is offline)

Notable enteries in logs:

When running a manual “retry” in the Remote Access menu, a WARN entry in the log appears right before failing with the following content;

[HttpClient/HCl#80] HTTP error requesting GET ``https://MY-IP.REDACTED.plex.direct:32400/identity`` (60, SSL peer certificate or SSH remote key was not OK) (SSL certificate problem: unable to get local issuer certificate)

2

Your server’s certificate is just ~1 day old and perfectly valid.

Did you set up a new server on MacOS, or did you transfer the plex data folder from Docker to your Mac?
If the latter, you may need to verify that all files within the plex data folder are readable and writable by your current server installation.

3

This is a brand new Plex Media Server Install, so I shouldn’t have any data from the old instance.

The only “migrated” data would be the media itself.

4

Update: I quite literally have no idea what caused this, but after a clean reinstall and purging all .plist entries with *Plex Media Server* in the name it looks to have fixed the issue. I’m wondering if there was a bad entry in there that got generated at some point, which was causing the Remote Access checks to fail. Nonetheless thank you for taking the time to take a look over this @OttoKerner. Appreciate it.