Is this setup safe and secure?

Question

My setup is to first connect to a VPN. Then run whonix using virtualbox. Then inside the whonix workstation, I installed normal firefox with a VPN addon to surf for websites that blocks tor. Basically like this:

user --> VPN1 --> tor --> VPN2.

Answer 1

First of all, I have to tell you that it it is a very dangerous to use the final addon VPN. Don't use it!

1. It probably came for free (since it is a Firefox addon), and free vpns are very unreliable. They have been known to keep logs, spy on users, have weak security, etc.

2. Never use addons with the Tor browser. The Tor Project has repeatedly stated that this is a bad idea for multiple reasons. If you want an in detail explanation, view my post here.

3. You say you are using the VPN addon because you want to access websites which block the Tor network. But how do you know that they won't block VPNs and proxies as well? Also, it is very easy to detect the Tor browser, so hiding your usage of the Tor network will only make you more fingerprintable to websites because you will be the only user who is using the Tor browser, but doesn't have a Tor exit node IP address. The VPN addon can also fingerprint you. This can greatly identify you.

Now let's answer your question.

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To answer your question specifically, I'll need more info. But I'll answer it with what I know.

One benefit from this setup is that traffic anaylsis done by Tor relays is almost impossible. Normally, both the entry and exit node are controlled by an attacker, who can correlate the two to figure out what site your IP address is visiting. However, in this case, no Tor node knows your IP address or traffic.

However, if someone controls both your entry and exit VPNs, then they might be able to conduct a traffic analysis attack as well. But since I don't know which VPNs you are using, I can exactly say how likely this is.

Furthermore, if your entry or exit VPN are hacked, you traffic or location could be exposed.

Also, you have make sure you trust both VPNs you are using. Do you trust that they have excellent security (to protect you from hacking), won't keep logs, spy on you, or help an adversary?

Additionally, you might want to consider the speed of your connection. It's probably slower with all extra VPNs.

Ultimately, I don't really think that this is the best setup to be totally safe and secure, though it isn't the worst. There are definitely weak points in the connection and you might want to reevaluate your current setup.

My advice: remove the final addon VPN, learn more about the security and trustworthiness of the VPN you first connect to, and ask other people about this as well. I hope this helps!

Here is a good article to look at: https://matt.traudt.xyz/posts/vpn-tor-not-mRikAa4h/

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Last but not least, here is what different entities know about your connection. I hope this provides you a clearer understanding of your security:

Your entry VPN knows your IP address (location) and that you are connecting to the first Tor node in your Tor circuit. It cannot see your traffic.

Your ISP cannot tell that you are using Tor and it cannot see your traffic.

The first Tor node knows that you have connected to a VPN before accessing the Tor network. It cannot see your traffic.

The second Tor node knows that you have connected to the first Tor node. It cannot see your traffic.

The third Tor node knows that you have connected to the second Tor node. It cannot see your traffic. It also knows that you are connecting to a VPN after your traffic goes through the Tor network.

Websites cannot see your traffic, do not know your IP address, and only know the IP address of the final VPN server.

Final VPN addon server (basically a proxy): It can see the sites you are connecting to and your internet traffic. If you have installed the VPN addon using Tor, then it does not know your IP address. If by chance during any communication between you and this final VPN where your IP address can be seen, the VPN will know your location and this is dangerous.

Note: if any of these entities communicates which each other, that could be an issue.

Answer 2

Well, that looks a bit like an overkill: you can and - IMHO - you should use the tunneling right, like this:

• You make every hop - both VPN's and Tor - just a routing VM
• You utilize the VirtualBox's HostOnly networks to avoid any data leaks without firewall rules overcomplication
• The last hop either runs a browser itself or it's providing a SOCKS5 proxy service with DNS for the local clients

All of these can be easily fit into the Raspberry Pi or a similar SBC and just be plugged in to your home LAN network and/or a router...