Reminds me of the bad old days of kermit and x/y/zmodem. http://www.extraputty.com/features/xmodem.html looks like a throwback to those days, over an ssh session. I wonder what you have to run on the server side for it to work?
Does uuencode or base64 work for you? I use it a lot to move stuff (aka my toolkit) to systems where I'm connected via citrix -> rdp -> ssh -> ssh. Amazingly, it works fine, though it can be slow.
$uuencode sheet1.xml sheet1.xml | pbcopy
(switch to remote session) $uudecode (paste, which varies depending on how I'm connected)
$ls -l sheet1.xml
Ta-da!