I have a Dropbox that I've maintained for nearly 14 years over various devices, and on my latest computer I've found that the files aren't syncing to offline mode automatically. I changed the setting that allows new files to be saved offline and not just to the cloud, but I can't seem to figure out to how to make sure that it downloads everything (almost 2GB) back to my new system.
I can wait for it for sync everything (though 90% is already on the computer, just in an older folder that the new installation of Dropbox refuses to use), but I can't figure out an easy option to do so.