Ask metadata for each file added to a folder (possibly many files added at the same time)

I have a file sync Windows desktop application that looks very much like Dropbox:

  • Tray icon is the only GUI.
  • Users mostly uses the Windows file explorer, but also programs such as MS Word that open and save directly from/to the local synchronized folder.
  • Whenever files are added to a given local folder, my app uploads them.

But now for a particular customer I have a new requirement: For each file to upload, first require the user to enter a description string. No file can be uploaded without a description (the server enforces this).

What would the most simple, user-friendly and efficient UI be for this?
At first I thought about a non-modal popup like this:

enter image description here

Note the absence of a "Cancel" button. Indeed, my app keeps files in sync, so the only alternative to entering a description and uploading the file would be to delete the file.

Users expect to enter a description for each file, so they probably will refrain from dropping 10000 files in one drop, but they might still do it by mistake. In that case I would suggest them to close my app and delete the mistaken files manually before restarting my app.

Let's say the user dropped 3 files, I wonder whether it is OK to show the popup 3 times in a row with just a different popup header, or whether the standard way to go in such cases is a more complex GUI with a kind of tasks queue, or something else entirely?

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