I am also having this issue suddenly after upgrading my Synology NAS DS916+ from Version: 7.2.1-69057 Update 3, to Update 4 recently.
Running on Windows 10, server has been fully functional with remote access enabled for 6+ years, with little to no issues.
Ran update over weekend, & since have only been able to sporadically keep server connection present in PMS (v 1.32.8.7639-fb6452ebf) for hours at a time.
Periodically the PMS software will either lose the connection to the server entirely, showing the “Can’t find connection to your server…” error from the PMS software for Windows, or the file relationship w the NAS disappears & the indexed files just won’t play because it thinks the connection to the network share is gone (even though it’s fully accessible from same network & files will play just fine).
Issue began when post-NAS software upgrade, I was attempting to validate remote access, & consistently failing. I did a bunch of reading to ID that some users reported disabling & re-enabling UPnP rescued their remote access file issues.
I attempted the same, & it did actually restore the issue but only temporarily. Issue keeps representing & so far the only short-term fixes (for what was an entirely reliable connection for the last few YEARS) is either constant reboots on the local host, re-mapping of the network drive, & rebooting network router.
Network gear is ASUS ZenWifi AX Mesh network with wired connection on same subnet for both NAS & host system running PMS.
Verified NAS file access works fine from hostname or IP address from local PMS machine but PMS software seems to keep losing either the NAS file access OR the actual pairing in PMS software to the entire server.
Any advice anyone can provide would be hugely appreciated because I’ve spent the last 5 days banging my head against the wall. Have also downloaded & reviewed the PMS logs unsuccessfully. Random errors reported in the logs but nothing that is clearly attributable to these types of network errors.
Coincidentally after the update, I also noticed what may be a sign of a db corruption as it reverted (possibly) years of indexed content from my “Recently Added TV” section, back to the most recent entries being files that were added a very long time previously. Though the library itself (AND the NAS file directories as well), still have the actual recently added files & shows.
Please, please, please, super Plexers - anything that can be offered to bread crumb me in the right direction, would be critical.
Thanks in advance 
Moved your post to a separate thread.
Where is Plex Media Server running, on the Synology NAS or on a Windows PC?
PMS is running on the win 10 box, files are stored on the NAS
Issue persists, but now I’ve noticed that it fluctuates between two circumstances:
1.) The server drops out entirely from the PMS UI, & is no longer connected nor recognized by PMS. In that event, I have to restart the PMS software on the local Win10 machine, & it typically restores service.
2.) The PMS software appears to lose the file association to the Synology NAS even though the server software hasn’t been interrupted or changed, & the NAS itself is still fully reachable by the local computer, both via hostname AND IP.
In this event, the only thing to restore it’s recognition of the files on the connected NAS is to restart the Win10 host. Thereafter, service returns to normal.
Issues #1 & #2 occurred yesterday in sequence separated by a few hours, & the restart in issue #2 has resolved it for the following 12-14 hours & the service has remained stable again since.
Intermittent / Sporadic outage to say the least.
Should I consider uninstalling & reinstalling the PMS software on the local machine (after backing up the DB?)?
Any advice is appreciated.
Thanks
Which Plex client are you using? Is it local or remote?
If the server has a keyboard & monitor, can you reach PMS on the server itself, http://127.0.0.1:32400/web?
This reads like Windows and/or networking problems. Nothing to do with the Synology.
Suggestion:
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Ensure Plex Media Server is configured for debug, not verbose, level logging.
Settings → Server_Name → General + Show Advanced
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Reboot the PC.
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Wait for the problem to reoccur.
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Restart Plex Media Server and wait 2 minutes for it to fully boot & log things.
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Pull the log files (Settings → Troubleshooting) and upload them to the thread.
Very odd but the PMS has been stable for 7+ days now. Will continue to monitor & conduct your troubleshooting suggestions as soon as the issue recurs.
Appreciate the tips
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