One of the things I’ve tried is to simply swap classes on input, so that if the user drags a file into the window, the entire window can receive the file. Otherwise, style it to look like a button in my rich text editor so that it behaves normally.

After successful drop, a small “Uploading” message is set with a fixed position, similar to gmail’s “sending…” message.

Upon successful upload, the final file location(s) (I’m resizing along the way) are sent back as jsonp so that img tags can be generated and inserted into the rich text editor.

Not feasible for say, a CMS with multiple Rich Text fields, but less does indeed seem to be more when it comes to managing user expectation of how dropping files should operate.

But the log property doesn’t carry over 90% of the time in the load event of the XHR… you must have realized this because this part is commented out in your live demo, which uses anonymous functions to keep a handle on the progress bar!