When uploading a file and the connection has been severed, but WinSCP hasn't detected it, WinSCP will pop up with the 15 seconds dialog and offer for you to try again. This seems to work ok, but in the transfer pane at the bottom, the old connection never goes away. It says "Connecting..." until WinSCP is restarted, even though the transfer finished on a different connection. Right clicking and selecting "Cancel" does not work.
Also, did you get the email and screen shot I sent you with the endless-loop connection issue?