SSL Error with Synology Server

Plex Media Server
1

Server Version#: 1.28.1.6104
Player Version#:
After updating my password due to the security breach, my Plex server now complains about an SSL error when I go into the server locally. I am running the server on an Synology NAS with its own lets encrypt cert and plex has always worked with the LE cert. But in the last 2-3 days Chrome issues a warning that the Cert is wrong

*This server could not prove that it is mydomainname.synology.me ; its security certificate is from .7e0747b55dba4afe80402cd0e1920a6f.plex.direct . This may be caused by a misconfiguration or an attacker intercepting your connection.

I’ve tried a full reinstall on Synology, new Plex user account etc but no change.

Any ideas why this might be the case?

Thanks
Paul.

2

You must add your certificate to Plex so it’s aware of, and accepts. it.

Settings - Server - Network - Show Advanced.

In the P12 you give it, you must also include the CA.

3

Thansk for the reply, but 've used plex for well over 5 years now and I’ve never had to do that. It has always worked with the cert that was applied to the NAS unit. Up to 4 days ago the same installation didn’t need Plex to have the LE cert details added to it. Is this a new requirement in the very latest plex server install?

4

The requirement has been there (when you use your own certificate) since sometime around 1.18.5-ish.

All you’re doing is telling PMS that your cert is originating requests.

NOW, one thing which can’t happen, and does happen on Synology (and other hosts) –

  1. You add a cert to DSM/NAS.
  2. ALL inbound to the NAS, regardless whether PMS or whatever, is grabbed by that certificate (the HTTPS connection to the host’s TCP/IP stack).
  3. DSM/NAS itself is hijacking the connection and creating a Man-in-the-middle “attack” which doesn’t really exist
  4. PMS has always reported them since it started allowing user certificates.
  5. PMS rejects these as you’re seeing now.

In summary, could this be DSM – Yes.
Is it a good idea to inform PMS and avoid the rejection – Yes.

5

I’m having similar issues since the latest update Plex doesn’t recognise my server. Infact I’ve been getting messages from Plex saying someone a third party has gained access to my Plex account but i think it’s actually myself. I had a problem about a year ago when my Synology Nas wouldn’t power on, so bought a newer Synology and migrated my stuff over. I’m pretty sure it must have something to do with this problem too but I’ve no idea how to sort it. Possibly a certificate issue.

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