[ilmiont]

Something like this was actually my original idea - just monitor a directory for changes. Then I've still got the issue of running this in the background, constantly, though, so the uploads occur automatically and keep running in background even after user logs out. (Monitoring is not as important as headless uploads)

[kgtm]

That shouldn't be an issue, why aren't you using tmux/screen in the first place? It's what most people use to persist sessions across logins (and much more, like terminal multiplexing). I personally use Byobu with the tmux backend on all my servers.

If you don't want to use extra software, a simple cron job running every minute would suffice.