So how do you go about using a VPN from inside a virtual machine? Do you install the VPN software on the host and set the virtual adapter to NAT (easiest to setup, I guess)? Do you install it directly on the guest and set the virtual adapter as bridged (no clutter at all in the host, provided it's even workable)? Do you install it on both the host and the guest and maybe do a crazy multi-cascaded double-chain of VPNs? I never tried to add VMs into the equation, and I'm definitely no VM or networking expert, but I basically have two concerns: whether the guest can connect at all through the VPN and whether the setup could be botched in some way so that your actual IP would still be exposed even when the guest is connected through the VPN. Anyone has done this already and can give me a nudge in the right direction?
With Tor I usually set up tor client on host and used iptables (Gnu/Linux) to redirect all traffic from guest OS to host virtual interface on host. Ideally it is best to have two guest machines: one for VPN client, second for browser or other software. Host redirects traffic from second machine to first.
See https://www.ivpn.net/privacy-guides/advanced-privacy-and-anonymity-part-1 Basically, you can do all that you mentioned.
I wouldn't want my ISP to know that I am connecting to tor. In fact, Tor is that last thing I would connect to.
Boy, talk about showing your work! Thanks for this, looks like I'll have interesting reading material for days. Might have saved me some blind googling. I'll have to evaluate what solution works best for me, but it's good to know all of the ones I had in mind are possible.
