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I have a couple of Virtualbox VMs (ubuntu guest) running on a windows 7 host, but internet access is through an authenticating proxy with a self signed certificate. Configuring this for just one of my VMs took several hours because of all the places I needed to add the authentication info and the manually installed certificates. To make the setup a bit easier, I am looking for some way to set up virtualbox witha transparent proxy so that I don't need to configure every program in each VM. AFAIK virtualbox itself doesn't have support for anything like this, so I assume I would need to set up a proxy server of my own (e.g. squid) to act transparently and forward all requests to the authenticating proxy. However, I have a few questions about this:

  1. Will squid be able to deal with the issue of self-signed certificates, or will I still need to manually install them on each VM?
  2. Would it be better to install squid in the windows host, or in a VM of its own? i.e. which will be easy to set up and work with? My instinct is to install it in another VM so keep the host clean, but I have no idea how to configure the network for that.
  3. Is there a simpler approach I'm missing?
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3.Is there a simpler approach I'm missing?

Perhaps:have you tried NATting your VMs? In other words,choosing a Natted network adapter, in the Network configuration GUI. In this case, all traffic from your pc will appear to originate with your host machine which,if I understand this right, is already authorized.

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NAT is the default, but it doesn't seem to solve the authorisation or certificates problem. Perhaps there is something else I need to configure? – aquavitae Jan 29 '14 at 6:29
@aquavitae Nope: it just means your LAN security is able to detect pcs hiding behind NAT, it is a serious security measure which is rarely implemented. It aims at forcing you to register, which appears at this point as the only solution you have. If you had used a Linux/Unix pc, there are countermeasures, but none that I know of in Windows. Sorry. – MariusMatutiae Jan 29 '14 at 6:50
Thanks for the info. I have successfully set up a transparent proxy before so that I only authenticate in one place, but that was in a single VM and it didn't deal with the certificates issue. – aquavitae Jan 29 '14 at 7:20

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