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I need to RDP to a terminal windows server 2003 OS and then RDP from there to my destination remote host. Same thing to SSH, first SSH to a CentOS via putty, then SSH to my destination remote CentOS host.

This is actually 2 different questions but same purpose. Is there any tool that can tunneling my connection, so I can directly RDP/SSH to destination. Thanks.

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tagged [ssl] because you mention SSL twice, but the question reads as if "SSL" is really a typo for "SSH". please correct or clarify. – quack quixote Jun 20 '10 at 4:34
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Your situation may not permit this, but if you can upgrade the publicly accessible server to Windows Server 2008, you can use Remote Desktop Gateway (also known as Terminal Services Gateway) to use the publicly-available computer to tunnel RDP sessions.

For SSH, although I don't know if you can do it in one step, you can use PuTTY to set up a local port which tunnels through the remote server and redirects to the second (internal) server. Then create a second PuTTY session to localhost using whichever port number you set up. This sounds like it's even more difficult than just using SSH in an SSH session like you have been doing.

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The RDP is pretty easy, I do it regularly as a kind of poor-man's VPN access.

When setting up your session, down in the SSH options are the tunneling options. You'll want to forward your local 3389 port to the remote's 3389 port. Once you've established your RDP session, connect to "localhost" and it should just come up. If the station you're on also has RDP enabled, forward port 3390 to the remote's 3389 port. You'd then connect to "localhost:3390".

SSL is much the same. Forward 443 to the remote's 443, and then you'd connect your browser to "localhost:443". It works, but expect all kinds of certificate validation failures when you do this, though.

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Can you be more clear, please? In 2nd & 3rd paragraph, what client are you referring to? I am assuming 3rd is using putty. What about 2nd one? Thanks. – Stan Jun 20 '10 at 6:56

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