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(I know there are a lot of questions regarding VPN+Tor. This is a bit different.)

I use a VPN to connect to the internet for multiple reasons, mostly to encrypt my traffic on local networks, e.g. public wifi. The VPN is on a dedicated server I own and runs a Linux distribution I fully control. I am the only one to have access to that server.

The problem is that my VPN IP address is strongly linked with my identity: the IP address is linked (with direct and reverse DNS) to a domain name related to my name (e.g. john-doe.com). So whenever I use my VPN the website I visit can know my identity. Thus all my online activities can be linked (and easily, just with my IP) to my real identity.

I could remove the DNS information but it's useful for various services I use on that server.

I could also set up a fresh server with no DNS name but in that case it would still be possible to track me (with more efforts) by contacting the server hoster which has my payment data.

My idea is to use Tor on that server so all internet from the VPN connection would be routed by Tor. Will it be a good idea? How to do that? Should I use a fresh server with no DNS information or I will be safe with my current VPN?

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Removing the reverse DNS doesn't matter because what the DNS used to be is sitting around in, for example the Rapid7 Sonar scans. They regularly scan the entire IPv4 address space's PTR records and publish the results. Your link to that server is baked into the internet and it will not go away.

Yes you will be linked by your payment data and following money trails.

If you want the anonymity properties of Tor, just disregard the server and use it for whatever. Run a relay but don't use it as part of your anonymity solution: this will fail!. Trying to utilise resources directly attached to you as part of a system of anonymity is going to be problematic.

Use Tor as it was intended to be used, your special-snowflake engineered "anonymity" "solution" will only distinguish you from all other Tor users and make you less anonymous.

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It will be safe with your current VPN in case if you'll set up an exit node with a good speed and access permissions : the traffic stream will be constant and solid. It would be almost impossible to separate your traffic from exited via the exit node you've made. If you need an assistance - just say it, I'll help you

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  • This doesn't hold. There are a few ways you could distinguish the users traffic from other exit traffic in the case of using a VPN.
    – cacahuatl
    Commented Jun 17, 2016 at 19:40

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