No fault of the engineer: THIS NEEDS TO GET BUILT INTO THE DAMN BROWSER.
Yes. Upload. With an actual progress bar. Built into the app you sit in all day. Imagine that.
Sending messages to a PHP server script so you can have the server tell you how many bytes were sent? Even the dumbest terminals knew how to show a bytes uploaded count with XMODEM in 1977.
Google Music installs a friggin client app to hash and upload your songs. DropBox still can't get drag and drop working and STILL limits files to 150MB if you upload via HTTP.
This is such a basic scenario I simply don't understand why it hasn't been solved. And don't even get me started on the Upload Straight to Amazon S3 via Flash/Silverlight doodads. Nobody can seem to get those working reliably either.