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I'm trying to connect to a Windows server from my Mac using RDC2.1 for Mac.

The problem is the server I need to connect to is guarded by the evil dragon - IP-based access control on a completely separate network.

I have an IP I can get in on, but it's at my office (i.e. a completely separate network).

Because that network isn't set up for VPN, I've set up a SOCKS proxy through an SSH tunnel (which is all working fine).

               (SSH proxy)
Me (on my Mac) ----------> Office Linux box ----> Windows server
(home network)             (office network)       (other network)

From my Linux server in my office (the SSH server) I can telnet to port 3389 on the Windows server, no problem. But from my Mac I can't get so much as a squeak out of it. Any ideas?

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So you're asking Sys Admins to help you bypass security put in place by Sys Admins? – GregD Dec 21 '10 at 13:37
"I have an IP I can get in on" - there would be no point having the security if I couldn't bypass it! That's like having a security guard at your front door and telling him to never let anyone in or out and him taking you very literally... – scrumpyjack Dec 23 '10 at 9:57
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closed as off topic by GregD, Zypher♦ Dec 21 '10 at 20:00

Questions on Server Fault are expected to generally relate to servers, networking, or desktop infrastructure, within the scope defined in the faq.

2 Answers

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You could try using CoRD, a replacement remote desktop app which supports SOCKS proxies.

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After downloading and using CoRD I already prefer it to Microsoft's own RDC... good find Marc – scrumpyjack Dec 23 '10 at 9:54
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up vote 3 down vote

You don't need a SOCKS proxy for this; simple SSH port forwarding will work. For example, there's a server at my office I frequently need to access, which we'll call server.example.com. I can't connect to it directly, but I can ssh to myofficemachine.example.com. So I do this:

ssh -L 3389:server.example.com:3389 myofficemachine.example.com

And then I point my local Remote Desktop client to localhost. This works great, and my setup is almost identical to yours -- a Mac at home, a Linux box at my office, and a Windows server on another work network.

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This did the trick nice and quickly! – scrumpyjack Dec 23 '10 at 9:53
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