Here's what my WinSCP script looks like so far:
# Automatically abort script on errors
option batch abort
# Disable overwrite confirmations that conflict with the previous
option confirm off
# Connect to SFTP server using a password
# Uploads all files in the dir
put C:\folderpath\* /FTPLocation/
Or does the file need signed outside of WinSCP?
So... Looks like this is done with the PGP tools... I'm just hunting for a freebie CLI based tool.. so I can sign my file using a bat command.