Server gets unvailable every couple days

Hi everyone, i’m not sure this is the right place, but i checked and didn’t find anything more suitable.
So i’m fairly knowledgeable when it comes to IT and Linux but here I’m just stuck.

PlexServer is running in a Ubuntu VM (Version: v1.16.4.1469) and just keeps becoming unavailable every couple of days (at one point even twice a day). Meaning, on the server the processes are all running but when trying to access the webapp or from my phone it just doesnt connect. On web its says “503 Service Unavailable”. When I restart the service systemctl restart plexmediaserver everything is fine afterwards. The logs dont give me much enlightenment, here is a filtered output (removed all debug for now):

root@plex:/var/lib/plexmediaserver/Library/Application Support/Plex Media Server/Logs# cat Plex\ Media\ Server.log | grep -v DEBUG
Aug 10, 2019 23:00:01.466 [0x7f495f017700] INFO - Plex Media Server v1.16.4.1469-6d5612c2f - Ubuntu PC x86_64 - build: linux-x86_64 debian - GMT 02:00
Aug 10, 2019 23:00:01.467 [0x7f495f017700] INFO - Linux version: 16.04.6 LTS (Xenial Xerus), language: en-US
Aug 10, 2019 23:00:01.467 [0x7f495f017700] INFO - Processor Westmere E56xx/L56xx/X56xx (Nehalem-C)
Aug 10, 2019 23:00:01.467 [0x7f495f017700] INFO - /usr/lib/plexmediaserver/Plex Media Server
Aug 10, 2019 23:37:01.301 [0x7f48f0ff9700] ERROR - Error issuing curl_easy_perform(handle): 7
Aug 10, 2019 23:37:01.301 [0x7f48f0ff9700] WARN - HTTP error requesting GET https://192-168-16-9.44c8a6525bcd46609c2c7553e7146024.plex.direct:32400 (0, No error) (Failed to connect to 192-168-16-9.44c8a6525bcd46609c2c7553e7146024.plex.direct port 32400: No route to host)
Aug 10, 2019 23:37:03.306 [0x7f494c9c5700] ERROR - Error issuing curl_easy_perform(handle): 28
Aug 10, 2019 23:37:03.308 [0x7f495c812700] ERROR - Error issuing curl_easy_perform(handle): 28
Aug 10, 2019 23:37:08.303 [0x7f48d0ff9700] WARN - Connection Tester: Error testing media server DockerPlex in 10000 ms.
Aug 11, 2019 03:37:01.203 [0x7f49367fc700] ERROR - OCSP: response error: unauthorized.
Aug 11, 2019 03:37:01.203 [0x7f49367fc700] INFO - OCSP: couldn’t fetch a valid response; retrying in 19200 seconds
Aug 11, 2019 08:57:03.950 [0x7f4934ff9700] ERROR - OCSP: response error: unauthorized.
Aug 11, 2019 08:57:03.950 [0x7f4934ff9700] INFO - OCSP: couldn’t fetch a valid response; retrying in 19200 seconds
Aug 11, 2019 11:36:59.033 [0x7f48d37fe700] WARN - Sync: sync list 27491989 belonging to user
1 (Eldiabolo18) has died of old age, ignoring
Aug 11, 2019 11:36:59.038 [0x7f48d37fe700] INFO - Sync: downloaded 2 sync list(s) with 3 sync items(s): 0 new, 0 updated, 0 deleted
Aug 11, 2019 11:36:59.423 [0x7f495d814700] INFO - OCSP: Successfully retrieved response from cache.
Aug 11, 2019 11:36:59.429 [0x7f495d814700] INFO - OCSP: Loaded a stale response from cache.
Aug 11, 2019 11:36:59.429 [0x7f495d814700] INFO - OCSP: Couldn’t install the cached response; fetching from network.
Aug 11, 2019 11:36:59.680 [0x7f48f0ff9700] ERROR - OCSP: response error: unauthorized.
Aug 11, 2019 11:36:59.680 [0x7f48f0ff9700] INFO - OCSP: couldn’t fetch a valid response; retrying in 19200 seconds
Aug 11, 2019 11:37:01.385 [0x7f49137fe700] ERROR - Error issuing curl_easy_perform(handle): 7
Aug 11, 2019 11:37:01.385 [0x7f49137fe700] WARN - HTTP error requesting GET https://192-168-16-9.44c8a6525bcd46609c2c7553e7146024.plex.direct:32400 (0, No error) (Failed to connect to 192-168-16-9.44c8a6525bcd46609c2c7553e7146024.plex.direct port 32400: No route to host)
Aug 11, 2019 11:37:03.390 [0x7f4912ffd700] ERROR - Error issuing curl_easy_perform(handle): 28
Aug 11, 2019 11:37:03.390 [0x7f49127fc700] ERROR - Error issuing curl_easy_perform(handle): 28
Aug 11, 2019 11:37:08.387 [0x7f48f37fe700] WARN - Connection Tester: Error testing media server DockerPlex in 10000 ms.
Aug 11, 2019 12:07:07.253 [0x7f495e816700] WARN - JobManager: Could not find job for handle 5934
Aug 11, 2019 18:20:35.475 [0x7f495d814700] ERROR - EventSource: Retrying in 15 seconds.
Aug 11, 2019 18:21:08.501 [0x7f495d013700] ERROR - EventSource: Retrying in 30 seconds.
Aug 11, 2019 18:21:58.502 [0x7f495d814700] ERROR - EventSource: Retrying in 15 seconds.

Has anyone an idea what i could try to resolve the problem, or even sees the problem?
Cheers Fabian

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