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We have a windows server 2003 machine with rdp service listening on the standard port 3389.

For security reasons this port is not opened on the router, but we have freesshd service running and a remote admin can login via ssh and this port is forwarded to external port 33001 for the first external user. This works great.

Now we have another admin who wants to work remote (he uses a different windows account, and connects from a different location, where he wants to use a dekstop, but needs to work on the same server.)

So this is basically a ssh port forwarding question.

Will the other user be able to login at the same time forwarding the same port 3389 to his machine?

Please keep in mind that there will be a second tunnel, and this second tunnel will also use the local port 3389 on the windows server.

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Maybe I'm not reading this correctly but it seems to me that it would be simpler to just have the admins create an SSH tunnel from the client end. – John Gardeniers Apr 22 '10 at 21:40
Yes, this is the plan. I will have to update the question and make it clearer, maybe add adrawing. – user12096 Apr 26 '10 at 9:29

Yes, it will work. Local port in ssh port forwarding is a port on ssh client, in your case your administrator's workstation. Since they obviously can't use the same machine at the same time, local ports can be the same.

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Aleksander, I am not sure if I understand your answer right. Windows server RDP was designed to accept 2 simutaneuos connections at the same time (on the same port) and that is exactly what we are trying to do. 2 people can work on 2 different desktops under their respective user accounts. – user12096 Apr 26 '10 at 9:19
Those are different levels, the number of RDP user sessions has nothing to do with TCP ports. Former is OSI layer 7 while the latter is layer 4, see – Aleksandar Ivanisevic Apr 28 '10 at 19:50

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