I decided to give plex pass a try so I could use Cloud Sync but every time I try to sync a file it transcodes fine but is then just stuck on “Waiting to be uploaded”. I have tried unlinking and re-authorising my dropbox account but it never uploads. Is there a solution to this or shall I just cancel my plex pass?
Hi,
It happens exactly the same, I bougth plex pass and cloud sync is stuck on “waiting to be uploaded” 
same here as well.
It’s really astonishing to me that this feature is advertised as part of Plex Pass and not only simply doesn’t work for apparently a large number of people but that Plex doesn’t even respond to inquiries requesting help.
I suggest using Emby for this instead. Their cloud sync service works perfectly well. Does exactly what this one does, except actually does it.
Would much rather use Plex for this but if you Google this, there have been massive problems with this feature dating back to at least 2014, only sporadic responses from Plex, and whenever it starts to work it appears to be within a couple weeks of stopping.
it’s a joke…