Using iCloud Drive with Shareboxed

The shortest connection Shareboxed has: nothing to set up, nothing to sign in to, no keys anywhere. If this Mac has iCloud Drive switched on, uploads land in it. And iCloud takes them from there to your other devices.

Press Test Connection to be sure: it asks Shareboxed to write a file into iCloud Drive and remove it again, which is the only thing that can be wrong before an upload.

What "finished" means here

An upload finishes when the file is in iCloud Drive. The same moment it would be finished if you had dragged it into that folder in Finder yourself. What happens after that is iCloud's: it uploads to Apple on its own schedule, and shows its own progress in Finder next to each file.

Shareboxed cannot show you that second half. macOS only reports upload progress for files inside an app's own iCloud container, a private space that appears in nobody's iCloud Drive. It tells an ordinary app nothing at all about the folder you can actually open. Rather than invent a spinner for a number we do not have, the progress bar stops where our part does.

If you want to watch the rest: open the folder in Finder. iCloud draws a small cloud beside a file that has not finished uploading yet.

Where the files go

Inside iCloud Drive, in Shareboxed's own folder, every upload session gets its own folder named with the date down to the second:

iCloud Drive/
  Shareboxed/
    2026-08-18 16-30-00/
      holiday photos/
        a.jpg
        b.jpg

Without that folder a second batch would quietly overwrite the first one's identically named files. Taking a file back out of a bucket before it is sealed removes it from iCloud Drive again.

Two things worth knowing

It counts against your iCloud storage. A 5 GB batch needs 5 GB of iCloud space, the same as any file you put there. Shareboxed does not clean up after itself: what you upload stays until you remove it.

Optimise Mac Storage may evict the local copy. If you have that on (System Settings → your name → iCloud → iCloud Drive), macOS may remove the downloaded copy of a file it thinks you are done with. The file stays in iCloud and comes back when you open it, but a folder that looks empty of data on this Mac is not a sign anything went wrong.

No shareable links

The Sharing switch is not offered for this connection. Shareboxed links work because we can sign one request for one file without handing anyone your account, and iCloud Drive has nothing of the sort to give: sharing there happens in the sharing sheet, as the person sitting at the Mac.

That sheet is right there, though. In Finder, right-click a file or the session folder → Share → Collaborate or Send Copy, and iCloud makes a link you can send. For a link Shareboxed itself hands you at the end of an upload, use an S3 or Cloudflare R2 connection.

When something does not work

Press Test Connection first. What it can say:

What you see	Fix
iCloud turned off	Turn iCloud Drive on in System Settings → your name → iCloud.
Insufficient permissions	Writing into iCloud Drive failed: it is still setting up, or the storage is full.
Not reachable	Shareboxed did not answer in time. Open Shareboxed and press Test Connection again.

Two more that only show up later:

Uploads land, other devices do not see them: iCloud is still uploading, or that device has iCloud Drive off.
Uploads stop with a write error: iCloud storage is full.