My first hunch is that gmail doesn't like this address. Have you tried to send a mail from gmail to that address?
Other then that it may have something to do with HTTPS alert returned from the mail server when trying to setup the session. In that case it will take a more thorough digging to troubleshoot.
yeap, its a windows issue. In linux\cygwin it works alright.
As for windows, when the dos window opens up you can right click the title bar, choose properties, choose layout tab, modify window size Width and Height values to your liking, choose the "save properties for future..." and click ok.