I don't understand how Tails -> TOR -> VPN can compromise anonymity if you use a free VPN?

Hello,

So obviously, I have read a lot about how using a VPN with TOR can compromise anonymity, but I fail to understand, if I use TOR and then connect to a VPN via the TOR network, how will anonymity be compromised?

The VPN will obviously be a free one so that I don’t insert my login credentials which can be used to de-anonymize me.

Can someone explain?

The whole idea of the Tor network, is to anonymize you, by selecting nodes and paths randomly in the middle of ~10000 nodes, to ensure no one can correlate what you send, and what is sent on the other side.

Now, guess what happens, if after sending all your traffic through those ~10000 different nodes and ~10000^3 paths, you send everything to one central node… Do one attacker still need to monitor all the different nodes and paths or just the central node ?

My understanding is that free VPNs store detailed logs and sell the data, which could potentially be used by an attacker to deanonymize you.

My recommendation would be to buy multiple shared VPN accounts (NordVPN, ExpressVPN keep minimal/no logs supposedly) and rotate between them so that the personal info associated with each account (payment info, etc) isn’t attached to you. In addition the traffic from other users on the accounts should help further obfuscate your browsing data.