Moving your existing library
To move an existing media library, run the pre-flight scan in Tools, check what it found, then start Offload everything in Jobs. Work runs in the background in small batches, with pause and cancel. New uploads offload by themselves. Each file keeps loading from your server until its cloud copy is verified.
Run the pre-flight scan
Open Offloft → Tools and click Run scan. The scan counts your media items and files and lists anything that needs attention first. Nothing is uploaded. If it's interrupted, click Finish the scan to continue.
From WP-CLI, run wp offloft scan.
Start the offload
Open Offloft → Jobs and start Offload everything. You can close the page: the work runs in the background.
Every file of every media item gets its own status. Large files go up in parts that resume after an interruption, and an upload that fails is retried with increasing waits.
From WP-CLI, run wp offloft offload.
Pause or cancel
You can pause a job after the media item in hand and resume it where it stopped. If you cancel, what's done stays done, and you can start again later.
When it finishes
Jobs shows the result, and Issues lists anything that couldn't be completed, with a fix where one is possible. Those files keep loading from your server, so nothing looks broken while you deal with them.
How long it takes
It depends on your server, the size of your library and your connection to the provider. The pre-flight scan gives an estimate based on your own server's speed.