I too am interested in such a feature. I suspect the most common reason a file is red crossed in the queue is because the file has been deleted from the server by the time it's place in the queue has arrived.
However I have noticed that sometimes a whole queue can be quickfire red crossed because some problem has cropped up in the open connection, but disconnecting and resetting the queue/clicking on go a bit later sees the files complete without a problem.
It's difficult to know how to handle a new feature like this, since sometimes an immediate retry isn't what you want.
How about something like this:
Option 1: If file is red crossed (failed), reset failed flag and put to end of queue. Retry failed file X times.
Option 2: If file(s) continue to fail, disconnect from site, reset all failed in queue and wait X minutes before "Go"
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