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I'm currently working for a company with quite strict security measures. 90% of my work takes place on a Linux machine, but to access this machine I first have to connect to a VPN, access a Windows VDIs, and from this I can access the Linux server via Putty.

This is fine for small tasks, but the majority of my work takes place on the shell this is slowing me down somewhat; I'm used to running multiple terminal windows and accessing servers via Emacs/Tramp.

I'm wondering whether it's possible to access the remote Linux server using my local SSH via the VDI, but I'm out of my territory when it comes to this sort of thing. I believe I can use Putty on the Windows VDI to act as a proxy for getting onto the Linux system, but it's the step before that to access the VDI using SSH where I'm getting stuck.

Should it be possible? If so, what sort of google searches should I be making?

Updated information:

  • I'm using the built-in OS X VPN tool.
  • The linux server can only be accessed via a machine on the same network, which is why we have to connect to a VDI first. I believe I can use Putty to open a connection to the linux server and make it act as a proxy on whatever port I wish, I just need to tell SSH to a) use the VPN settings and b) connect to the VDI.
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    I strongly suggest you ask this question of your information security officer at SecretCorp rather than here. Even if technically possible, even if as fundamentally as secure as the indirect method they have you use, any deviation from policy may be viewed (properly or not) as a violation and could have legal ramifications beyond merely getting fired. I'm not saying this is Right or Good, but it does happen, 'specially when us Unix freaks do something that isn't in the Windows manual.
    – msw
    Sep 19, 2013 at 11:08
  • @msw right. Although somebody creating a solution where words "security" and "windows" appear in one sentence without an odd number of negatives is probably not going to be overly accessible to any suggestions.
    – peterph
    Sep 19, 2013 at 13:25
  • Being such a tight security question at the infrastructure level, I think this question is better suited for ServerFault.
    – Tim
    Sep 19, 2013 at 13:27
  • @msw I totally understand, and I'm willing to take the risk. Generally the security measures set-up within the company are simply theatrical, and TBH I'll still be following their rules: I'll be using the VDI to access the linux server, and I will be using Putty to do so.
    – Phillip B Oldham
    Sep 20, 2013 at 8:41
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    @unpluggd - I would suggest you strip out the whole notion of VDI from your question. It's not really relevant and is just confusing the issue. The heart of what you're trying to do is from a Linux system, through VPN you wan to connect to a Windows system, which from there you can connect to other Linux systems.
    – slm ♦
    Sep 20, 2013 at 8:45

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What's the VPN technology/client you're using? Is it Linux based? It might be possible, but there are several stumbling blocks here. For one they may be limiting the access the Linux systems so that they're only accessible via the IP's of the Windows VDI, for example. There are others.

On the surface it should be possible but it may be a bit of a tough road to hoe.

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  • I've updated the question with further information. And yes, I know it will be a pain to set-up, but it will be more than worth it to increase my productivity.
    – Phillip B Oldham
    Sep 20, 2013 at 8:41

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