So restarted the server, but I still got the same message? 
What I did:
service plexmediaserver stop
tail /var/lib/plexmediaserver/Library/Application\ Support/Plex\ Media\ Server/Logs/Plex\ Media\ Server.log
Oct 27, 2021 16:42:05.128 [0x7fc976e0fb38] WARN - NAT: PMP, timed out waiting for response.
Oct 27, 2021 16:42:19.188 [0x7fc974d28b38] WARN - [CERT] TLS connection from [::ffff:192.168.1.9]:52498 came in with unrecognized plex.direct SNI name '192-168-1-9.d7ede18c3ab140f1964a21e4966c632c.plex.direct'; using installed plex.direct cert
Oct 27, 2021 16:42:19.215 [0x7fc974d28b38] WARN - [CERT] TLS connection from [::ffff:192.168.1.9]:52500 came in with unrecognized plex.direct SNI name '192-168-1-9.d7ede18c3ab140f1964a21e4966c632c.plex.direct'; using installed plex.direct cert
Oct 27, 2021 16:42:49.246 [0x7fc974d28b38] WARN - [CERT] TLS connection from [::ffff:192.168.1.9]:52502 came in with unrecognized plex.direct SNI name '192-168-1-9.d7ede18c3ab140f1964a21e4966c632c.plex.direct'; using installed plex.direct cert
Oct 27, 2021 16:42:49.276 [0x7fc974d05b38] WARN - [CERT] TLS connection from [::ffff:192.168.1.9]:52504 came in with unrecognized plex.direct SNI name '192-168-1-9.d7ede18c3ab140f1964a21e4966c632c.plex.direct'; using installed plex.direct cert
Oct 27, 2021 16:42:58.951 [0x7fc9776edb38] WARN - JobManager: Could not find job for handle 14675
Oct 27, 2021 16:42:58.962 [0x7fc9776edb38] WARN - JobManager: Could not find job for handle 14469
Oct 27, 2021 16:42:58.980 [0x7fc9776edb38] WARN - JobManager: Could not find job for handle 14563
Oct 27, 2021 16:42:58.980 [0x7fc9776edb38] WARN - JobManager: Could not find job for handle 14565
Oct 27, 2021 16:42:59.051 [0x7fc97ad6b6e8] INFO - Killing process: Plex Relay (pid: 14818)
Then waited for a bit and do the restart:
sleep 120 ; service plexmediaserver start ; sleep 10 ; tail n 40 -F /var/lib/plexmediaserver/Library/Application\ Support/Plex\ Media\ Server/Logs/Plex\ Media\ Server.log
Oct 27, 2021 16:46:53.464 [0x7f7133afeb38] INFO - Plex Media Server v1.24.5.5173-8dcc73a59 - Ubuntu PC x86_64 - build: linux-x86_64 debian - GMT -07:00
Oct 27, 2021 16:46:53.464 [0x7f7133afeb38] INFO - Linux version: 18.04.6 LTS (Bionic Beaver), language: en-US
Oct 27, 2021 16:46:53.464 [0x7f7133afeb38] INFO - Processor Intel(R) Core(TM) i5-2520M CPU @ 2.50GHz
Oct 27, 2021 16:46:53.464 [0x7f7133afeb38] INFO - Compiler is - Clang 11.0.1 (https://plex.tv e0c29d5827bc4eaaa2ceb882cbeed224b0960173)
Oct 27, 2021 16:46:53.464 [0x7f7133afeb38] INFO - /usr/lib/plexmediaserver/Plex Media Server
Oct 27, 2021 16:46:53.540 [0x7f713713a6e8] INFO - [CERT/OCSP] Successfully retrieved response from cache.
Oct 27, 2021 16:46:54.797 [0x7f7130d72b38] WARN - [MediaProviderManager] Unrecognized MediaProvider feature: availability
Oct 27, 2021 16:46:54.797 [0x7f7130d72b38] WARN - [MediaProviderManager] Unrecognized MediaProvider feature: availability-platforms
Oct 27, 2021 16:46:54.829 [0x7f7130e83b38] WARN - [MediaProviderManager] Unrecognized MediaProvider feature: availability
Oct 27, 2021 16:46:54.829 [0x7f7130e83b38] WARN - [MediaProviderManager] Unrecognized MediaProvider feature: availability-platforms
Oct 27, 2021 16:46:57.071 [0x7f71310d4b38] WARN - [EventSourceClient/pubsub] MyPlex: attempted a reachability check but we're not yet mapped.
Oct 27, 2021 16:46:57.162 [0x7f7130882b38] INFO - Sync: downloaded 0 sync list(s) with 0 sync items(s): 0 new, 0 updated, 0 deleted
Oct 27, 2021 16:47:03.269 [0x7f7130b85b38] INFO - LibraryUpdateManager path watching is disabled
Oct 27, 2021 16:47:05.250 [0x7f71302b2b38] INFO - [PlexRelay] Allocated port 27317 for remote forward to 127.0.0.1:32401
Oct 27, 2021 16:47:05.471 [0x7f713097db38] ERROR - downloadContainer: expected MediaContainer element, found Error
Oct 27, 2021 16:47:05.471 [0x7f713097db38] ERROR - IVA: Error downloading trailers for source 1.
Oct 27, 2021 16:47:05.573 [0x7f713097db38] ERROR - downloadContainer: expected MediaContainer element, found Error
Oct 27, 2021 16:47:05.573 [0x7f713097db38] ERROR - IVA: Error downloading trailers for source 2.
Oct 27, 2021 16:47:07.097 [0x7f7130ca0b38] ERROR - Error issuing curl_easy_perform(handle): 7
Oct 27, 2021 16:47:07.097 [0x7f7130ca0b38] WARN - HTTP error requesting GET https://192-168-1-2.070a15918a3c45058d0acbfbbd06b777.plex.direct:32400 (7, Couldn't connect to server) (Failed to connect to 192-168-1-2.070a15918a3c45058d0acbfbbd06b777.plex.direct port 32400: Connection refused)
Oct 27, 2021 16:47:07.976 [0x7f7130e07b38] ERROR - Unknown metadata type:
Oct 27, 2021 16:47:10.881 [0x7f7130d09b38] ERROR - Unknown metadata type:
Oct 27, 2021 16:47:11.122 [0x7f71302d5b38] INFO - AutoUpdate: no updates available
Oct 27, 2021 16:47:11.679 [0x7f7130d2cb38] ERROR - Unknown metadata type:
Oct 27, 2021 16:47:11.886 [0x7f7130cc3b38] WARN - NAT: PMP, timed out waiting for response.
Oct 27, 2021 16:47:12.098 [0x7f713095ab38] ERROR - Error issuing curl_easy_perform(handle): 28
Oct 27, 2021 16:47:19.500 [0x7f71310d4b38] WARN - [CERT] TLS connection from [::ffff:192.168.1.9]:53014 came in with unrecognized plex.direct SNI name '192-168-1-9.d7ede18c3ab140f1964a21e4966c632c.plex.direct'; using installed plex.direct cert
Oct 27, 2021 16:47:19.526 [0x7f71310d4b38] WARN - [CERT] TLS connection from [::ffff:192.168.1.9]:53016 came in with unrecognized plex.direct SNI name '192-168-1-9.d7ede18c3ab140f1964a21e4966c632c.plex.direct'; using installed plex.direct cert
Oct 27, 2021 16:47:43.834 [0x7f7130d2cb38] ERROR - Unknown metadata type:
Oct 27, 2021 16:47:49.600 [0x7f71310f7b38] WARN - [CERT] TLS connection from [::ffff:192.168.1.9]:53052 came in with unrecognized plex.direct SNI name '192-168-1-9.d7ede18c3ab140f1964a21e4966c632c.plex.direct'; using installed plex.direct cert
Oct 27, 2021 16:47:49.627 [0x7f71310d4b38] WARN - [CERT] TLS connection from [::ffff:192.168.1.9]:53054 came in with unrecognized plex.direct SNI name '192-168-1-9.d7ede18c3ab140f1964a21e4966c632c.plex.direct'; using installed plex.direct cert
^C
I also checked that the perms are ok before hand with chown -R plex:plex /var/lib/plexmediaserver so I can discard that.
I was trying to check a p12 cert that is on my side, but it seems to be protected by either a key or a password that I don’t have:
ls -l /var/lib/plexmediaserver/Library/Application\ Support/Plex\ Media\ Server/Cache/cert-v2.p12
-rw-r--r-- 1 plex plex 5753 Oct 27 14:06 '/var/lib/plexmediaserver/Library/Application Support/Plex Media Server/Cache/cert-v2.p12'
openssl pkcs12 -info -in /var/lib/plexmediaserver/Library/Application\ Support/Plex\ Media\ Server/Cache/cert-v2.p12
Enter Import Password:
^C
Should I remove the cert-v2.p12?
or any other suggestion?