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I've tested this several times now and it's the same on each occasion no matter the combination or type of files. If you select multiple files and then drag and drop them into the editor, only the first selected file is uploaded.
Tested in the latest versions of Google Chrome, Firefox and Safari on Mac OS Sierra.
This is roughly how the underlying support within Froala is designed. We may be able to change this by essentially just ripping out the behavior and doing our own thing, though the image dragging support isn't something we want to lose.
This wouldn't really be considered a bug in Froala but a feature/enhancement request, though I will pass it on. Making significant changes here wouldn't be a high priority. At this point, I'm going to leave this open but tag it as third party.
Thanks for this. I hope that Froala consider this for implementation. Typically in Redactor I would select and drag multiple files into the editor to upload them, now I will be forced to use the attach files link.