Has anyone managed to upload a zip / tar.gz of the 'uploaded files' directory from local machine to the cloud? There is no useful documentation I can find about this To make things worse, if you restore a database backup (i.e. a pgsql dump) any uploaded files are deleted at the same time.
This will function correctly, in older versions the data in the zip should be the content of the files directory without the files directory itself.
Maybe if you run into issues this could be the cause of the files not being uploaded correctly.
See this version 3 documentation page, it might still apply...
I do agree that more documentation on this matter would be good.