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File Drop turns any files or folders into a single shareable link, the fast way to hand a bundle of context to an LLM.
File Drop — drag and drop zone

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Open it

Press ⌃ ⌥ L from any app. Or skip the shortcut: shake a file you’re already dragging and a drop shelf appears under the pointer.

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How it works

1

Open the drop window

Press ⌃ ⌥ L. A drop window floats up and stays up while you drag from Finder.
2

Drop your files

A single file of any kind uploads as-is. Multiple files or a folder are bundled into one zip, then uploaded.
File Upload — drop files or folders here
3

Upload

Click Upload. The link lands on your clipboard. Paste it to any LLM.

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Shake to drop

Pick up a file anywhere, wiggle it while still holding, and a dark drop shelf appears under the pointer. Drop on it and the upload starts immediately — no ⌃ ⌥ L needed.
  • On by default, with a one-time explanatory toast
  • Switch it off in Settings → Tools → File Drop → Shake to drop
  • Three quick horizontal direction reversals trigger the shelf
Select several files in Finder and drag them in together. File Drop keeps them as one batch.

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Limits & notes

  • Up to 256 MB per upload.
  • Links expire automatically after 90 days.
  • Files only leave this Mac when you click Upload, never on drop.
  • Closing the window no longer cancels the upload — it continues in the background.