Windows CE development is not as fun as Linux because of the lack of open source tools. However, once I am able to make ssh server and client running on it, it becomes better. Here is how to get ssh server and client running on windows CE 5 (ARM based):
1. Download CESSH at http://www.codeplex.com/wikipage?projectname=CESSH
Download sshd_config at http://www.codeplex.com/Project/Download/FileDownload.aspx?ProjectName=CESSH&DownloadId=3561
Download file http://www.codeplex.com/Project/Download/FileDownload.aspx?ProjectName=CESSH&DownloadId=3562
2. copy the files to your windows CE device, suppose "\ssh"
3. mkdir "\Hard Disk"
4. copy sshd_config "\Hard Disk"
5. mkdir "\NandFlash"
6. mkdir "\NandFlash\ssh"
7. copy ssh_host_dsa_key to "\NandFlash\ssh"
8. run "adduser.exe root rootpass" to add the user "root" with password "rootpass"
9. copy SocketToFile.DLL to \windows
10. run "sshd.exe"
To test it, get pocketputty
If make this work over ActiveSync, use the remote port tunnel in putty.
Another great tool to have is netcat for CE: http://www.dr-bischoff.de/wince/Andreas_WINCE_stuff.html#netcat
Hope this helps.