I’ve used Plex for a few years, and have had an odd sync issue or two, but never something like this.
I recently rebuilt my computer, and reinstalled Plex fresh. At the same time, I got a new Surface. Though my other (Android) clients can sync to the Plex server just fine, the Windows 10 app will not sync due to “A Server Error Occurred During Sync”
The Plex server log looks normal, but I get an error on the client log (the only thing I have changed is replace my actual ip with “internalip” or “externalip”
017-12-30 17:42:40:1320 [22] DEBUG - [SyncListManager] - Asking server Michael to refresh sync lists
2017-12-30 17:42:40:1481 [22] DEBUG - [PlexHttpClient] - PUT https://internalip-internalip-internalip-internalip2fd364c2b3864354bb91bc05484163ab.plex.direct:32400/sync/refreshSynclists?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
2017-12-30 17:42:40:1706 [22] INFO - [SyncListManager] - Downloaded 3 sync item(s)
2017-12-30 17:42:40:1706 [22] DEBUG - [SyncOperation] - Finished refreshing sync list: 3 sync item(s)
2017-12-30 17:42:40:1757 [22] VERBOSE - [SyncOperation] - Run: Refreshed sync list in 0:00:20.4161005
2017-12-30 17:42:40:1757 [22] DEBUG - [SyncOperation] - Initializing server list
2017-12-30 17:42:40:1757 [22] VERBOSE - [PlexServer] - Testing 2 connections out of 2 for Michael
2017-12-30 17:42:40:1817 [10] DEBUG - [PlexHttpClient] - GET https://10-7-1-3.2fd364c2b3864354bb91bc05484163ab.plex.direct:32400/sync/transcodeQueue?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
2017-12-30 17:42:40:2006 [22] DEBUG - [PlexHttpClient] - Received OK from https://internalip-internalip-internalip-internalip.fd364c2b3864354bb91bc05484163ab.plex.direct:32400/sync/transcodeQueue?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
2017-12-30 17:42:40:2016 [10] VERBOSE - [PlexClient] - Container from https://10-7-1-3.2fd364c2b3864354bb91bc05484163ab.plex.direct:32400/sync/transcodeQueue?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx has 0 child item(s)
2017-12-30 17:42:40:2276 [5] DEBUG - [PlexConnection] - Last successful communication to https://internalip-internalip-internalip-internalipfd364c2b3864354bb91bc05484163ab.plex.direct:32400 happened at 12/30/2017 17:42:40, not retesting (connection is already the active one for device)
2017-12-30 17:42:40:2419 [10] DEBUG - [PlexConnection] - Testing connection to https://externalip.externalip.externalip.externalipfd364c2b3864354bb91bc05484163ab.plex.direct:32400 with a timeout of 00:00:20
2017-12-30 17:42:40:2429 [10] DEBUG - [PlexHttpClient] - GET https://externalip.externalip.externalip.externalipfd364c2b3864354bb91bc05484163ab.plex.direct:32400/?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
2017-12-30 17:42:40:2473 [5] DEBUG - [PlexDevice.TryTestConnectionAsync] - Comparing Michael connections with preferLocal=True: https://10-7-1-3.2fd364c2b3864354bb91bc05484163ab.plex.direct:32400 (Available) vs https://10-7-1-3.2fd364c2b3864354bb91bc05484163ab.plex.direct:32400 (Available) = 0
2017-12-30 17:42:40:8040 [18] DEBUG - [PlexHttpClient] - Received OK from https://internalip-internalip-internalip-internalipfd364c2b3864354bb91bc05484163ab.plex.direct:32400/sync/refreshSynclists?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
2017-12-30 17:42:41:2700 [22] WARNING - [PlexHttpClient] - (HttpRequestException->Exception) from https://75-137-233-163.2fd364c2b3864354bb91bc05484163ab.plex.direct:32400/?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx: The text associated with this error code could not be found.
A connection with the server could not be established