Not sure if this has been reported, although I've seen things similar
I think I may have found a bug. When you use WinSCP with the /upload switch, it asks you to determine how to send the file (binary, automatic, etc.) Even if you check 'Use these settings next time', it will still ask you again when you run the program the next time. I was wanting to have WinSCP automatically upload a file every morning, so I didn't know if this was a bug or if I was doing something wrong.