How do I tunnel an HTTPS proxy through a virtual machine (VMWare)

Posted by Kyle on Server Fault See other posts from Server Fault or by Kyle
Published on 2011-12-13T00:25:15Z Indexed on 2013/10/20 9:58 UTC
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I have a personal setup at home using VMWare Workstation. I also have a set of Virtual Private Machines that run Squid, and therefore provide me HTTPS proxy tunnels. Using Proxifier, I can tunnel all traffic for given applications through these tunnels.

However, I also have a few virtual machines for dev/staging/experimentation/etc. I generally just use NAT to provide Internet access to the machines, and if I need to use these proxies, I can just setup Proxifier (or a Linux equivalent) to pipe the traffic through them. No problem.

But... I got to thinking: Wouldn't it be great if I could assign these proxy tunnels to a virtual machine, so that when I start up the VM, it has instant-on access through the tunnel and not my local connection? (EDIT: Of course, it would USE my local connection, but it would tunnel traffic through the proxy.)

To be more clear: I want a solution that binds the proxy to a VM, so that when I start the VM, I don't have to use a proxy client to connect to the tunnel - I am already piping all traffic from that VM through that proxy.

I did a bit of searching, and the closest thing I could find was this:

How to route public static IP to a virtual machine on a vmware ESXi host?

Which wasn't all that applicable.

The proxies are protected by user/pass but do not filter by IP. Again, they are HTTPS proxies setup through Squid.

Any ideas on how to make this happen? Thanks a ton.

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