TOR + VPN combinations: Would it be safer?

I plan to use chain: Whonix-Workstation → Whonix-Gateway → sys-vpn → sys-firewall → sys-net
On Whonix-Workstation, I plan to connect under rdp to a remote dedicated server with qubes + whonix OS installed. On a remote dedicated server, I plan to implement the same chain with another VPN provider (Whonix-Workstation → Whonix-Gateway → sys-ANOTHER-vpn → sys-firewall → sys-net).
I plan to work with Whonix-Workstation, which is located on a remote dedicated server

My question is: does this chain look more anonymous than if I were working without a remote dedicated server?

Thanks for answers

You are adding a lot of static point in your setup. The VPN on your side is not necessary at all. if you need to hide the fact that you are using TOR, check the different relay options that you have to hide it. Also, doing the same thing on the remote server is redundant imo. Set the VPN there instead of your machine and you’ll have something solid. If you need more information, the Whonix forum seem more suited for this kind of question.

Did you ever try to ask yourself: “Why do I trust to VPN companies they will preserve my anonymity?”

For me, it is needed to access sites that block tor. But I use only free VPNs and not for sites that can profile me. For example, Quora blocks tor and sometimes I need to access it. Then I use either free VPN through tor, or while using tor just access the page via
I would never use VPN after tor and paid for it?! Where’s there anonymity?! If I can pay to VPN company and stay anonymous, then the fact makes VPN pointless.

The first line in his post shows that sys-vpn is connected to sys-firewall, which means that it reaches the VPN server first, then it sends the TOR encrypted packets to the first node in the circuit. That’s why I said it wasn’t necessary here because there are already a few different relay types you can use with TOR instead.

Absolutely. It was clumsy on my side the way I tried to continue your thought when and how it sounds reasonable to use VPN, at least for me. Thanks for pointing out how my post was read the way it wasn’t intended to.

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