Cascading VPNs with Tunnelblick?

[a3r...@gmail.com]

Hi there,

is it possible to cascade VPNs in Tunnelblick?
E.g. I have an account at VPN1 and VPN2. I connect to VPN1 first and tunnel the tunnel through VPN2.

This feature -when used within one provider- is called multi hop VPN. I want to do it with 2 providers

[Tunnelblick developer]

It is possible, but extremely difficult to set up, so unless you have a lot of networking and scripting expertise, you probably can't do it.

However, you should read Tunnelblick and VPNs: Privacy and Security, which explains what VPNs can and cannot do to protect your privacy (tldr: not much, depending on who is trying to track you). (Everything in that article applies to multi-hop VPNs, too.)

It requires customized "up" and "down" scripts to handle DNS and routing. They would be extremely complicated to set up, especially if you have not set up each of the VPNs yourself (which seems to be your situation), because you can't rely on any specific networking setup (e.g., IP addresses and subnets) for either VPN.

[a3r...@gmail.com]

Thank you!
Actually, I'm pretty aware about the privacy implications, this was more of a theoretical question than a practical. But it sounds like a hassle, I think it would be easier to set up an intermediary client on my router (and my raspberry pi access point).
One piece of infrastructure is actually under my control(-ish)