'Waiting To Upload' error anyone?

I have Plex Pass and a cloud server setup through Google Drive with plenty of space (about 25GB) left, yet I have about 4-5 movies still in “Waiting To Upload” stage (Big Hero 6 in attached screenshot).

My main server is on my MacBook Pro but I’m not sure if that’s relevant. I have 25-30 movies in the cloud server that uploaded and synced fine, but these 4-5 are just stuck. Anyone having this issue or know of a fix?

Also, I run Plex on my Apple TV in my bedroom. I’ve noticed on the Apple TV that my cloud server isn’t even showing up as an option? Is this a common problem?

I have been having similar issues with my Cloud sync. I have tried add/removing both google and dropbox, and while they were working last year, it has been broken nearly 6 months for me.