File transfer using telnet

Not exactly following what you are trying to do...

However, you can specify telnet commands on a host by host basis, or set it for all hosts with the DEFAULT host, with your $HOME/.telnetrc or /etc/telnetrc files. See the 'open host' part of the telnet man page.

From the man page for (rsync on my OpenBSD 4.9 box):

There  are  two  different  ways  for rsync to contact a remote system:
using a remote-shell program as the transport (such as ssh or  rsh)  or
contacting  an  rsync daemon directly via TCP. 

The point is I believe you can use rsync to connect using the first setup referred to above (remote-shell program as the transport) and get a broken connection resume for free by doing something like this:

$ rsync -r -h -P -e "ssh -p 1234" user@host:/my/huge/file   anotherUser@anotherHost:/destination/

[Note on the switches: -r for recursive, -h for human-readable, -P for --partial (keep partially transferred files), and -e for specifying the remote shell to use. You can also use --partial-dir = DIR if you want to get fancy.]

and under this scenario you don't have to have an rsync server running on the windows box -- just an ssh server. There are many ssh servers to choose from that you can use on the windows platform (I suggest putty since this has the GUI setup familiar to win guys).

I'd also use md5 to hash your file and compare the transferred file's md5 to make sure your file is properly transferred and just keep firing off a script which keeps rsyncing from the linux side until you get your properly transferred file sitting pretty on the win box.