I've been trying to upload to a server (using SFTP-3) and when an error occurs, WinSCP won't reconnect automatically, but instead sits there waiting for me to click "Reconnect" from a popup window. If I am not around to click it, by the time I come back, I have to start the transfer again. I have the following configuration:
1) Background transfer is enabled by default
2) "No confirmations for background transfers" is enabled
3) "Automatically reconnect session if it breaks during transfer" is enabled, set for 2 seconds.
4) "Enable transfer resume" is enabled for files above 100kb (the file I am trying to upload is above 100kb)
I didn't try the upload in the foreground. I will try it.
Over the various attempts, I got two types of error messages. One was something to do with a 'network' error, the other 'software'. I know these are vague responses to your questions - I will try to re-run the upload to get more specifics.