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:
- 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?
- 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.
- Is there a simpler approach I'm missing?