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• Dragging and dropping a file replaces the old upload. If the old upload was linked, the link stops working
• It's not entirely clear where exactly to drop the file in the first place

A workaround right now is clicking "preview" after uploading a file and then dragging and dropping in the second file

1. Drag and drop file on or next to "Browse"
2. Click insert link
3. Drag and drop another file
4. Observe original file getting replaced, and the old file link stops working

Being able to drag and drop multiple files and ideally seeing where to drop them while dragging