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This is how I got SSH and CVS to work together!
The trick was in how to set up the CVSROOT variable.
I did this on NT4, but it should be similar for 95/98 and OS/2.

First I set up SSH, using the following steps:

1) I pointed my web browser to ftp://ftp.cs.hut.fi/pub/ssh/contrib/
2) I downloaded the ssh-1.2.14-win32bin.zip file
3) I unzipped the file into a directory that was already on my PATH
4) I created a directory E:\hb-dev\ for my Harbour development CVS tree
5) I created a batch file LOGIN.BAT, in the E:\hb-dev\ directory, with
   the following commands in it:
      @echo off
      SET HOME=E:\hb-dev\
    ssh -l dholm Harbour-project.sourceforge.net
6) I ran the LOGIN batch file, which automatically created a .ssh
   directory under E:\hb-dev\, automatically accepted the key from
      SourceForge, and prompted me for my  password.
7) I entered my password and got logged into a SourceForge shell,
   thus confirming that SSH is configured properly.
8) I entered "exit" to quit back to the DOS prompt.

Next I set up CVS, using the following steps:

1) I pointed my browser to http://download.cyclic.com/pub/cvs-1.10/windows/
2) I downloaded the cvs-1.10-win.zip file
3) I renamed my old CVS.EXE to CVS-OLD.EXE
4) I unzipped the new file into a directory that was already on my PATH
5) I created a batch file CHECKOUT.BAT, in my E:\hb-dev\ directory,
      with the following commands in it:
      @echo off
      SET HOMEDRIVE=E:
      SET HOMEPATH=/hb-dev/
      SET CVSROOT=:ext:dholm@cvs.Harbour-project.sourceforge.net:/cvsroot/Harbour-project
      SET CVS_RSH=ssh
      cvs co harbour
6) I ran the CHECKOUT batch file and was prompted for my SourceForge
   password. And it checked out the entire harbour CVS tree!

So all you have to do is make the obvious substitions for drive letters,
path names, and user IDs, and this procedure should work for you.
You may not even have to download a new copy of CVS, but you may
have to have a text mode version of SSH.

I found the trick to setting up the CVSROOT properly by doing a search for
"CVS SSH NT" at http://www.google.com/ and following the third link, named
"Configuring WinCVS and Secure SHell on Windows NT" and located at
http://www.cc.gatech.edu/classes/RWL/Projects/scenicview/Web/cvs-ssh-config.html

David G. Holm, Set Captain and all around
Harbour Project Clipper Compatibility fanatic.