I can fix this by allowing insecure connections but what I cannot figure out is how I flush the SSL cert or reissue it.
As far as I can tell the refresh has to come from Plex supports end? ( Based on @ChuckPa manually reissuing them in other support threads ). Is that correct or can I force a new SSL cert on my end?
Verify your Plex Media Server version. It will be 1.x, not 4.x. Settings → Server_Name → General
or Authorized Devices
Synology model?
The Plex Media Server version provided by Synology is out of date. If you are using that version, download a current version from plex.tv and perform a manual update.
If you are running an old version of PMS, you are probably running into this problem:
(Kicking myself I missed the linked thread as I was searching around SSL/certificate issues and the error code. Hopefully if anyone else stumbles onto this thread they will at least find your solution quicker than I did!)