A VPN would not cover up the fact that you used Tor at all. Assuming you're actually utilizing SSH through sock proxies and using a VPN, you can still be finger

A VPN would not cover up the fact that you used Tor at all. Assuming you're actually utilizing SSH through sock proxies and using a VPN, you can still be fingerprinted and tracked. There are already existing databases that have established profiles for various sites. Your ISP can easily see if you're connecting to one of those sites based on the type of data you're sending. Regardless if it's encrypted. On the other hand, if you normally do this but forget to one time, it doesn't mean you're automatically exposed. It simply means that if anyone is currently attempting to find you and have an exploit that will actually work on you, then they will be getting you directly instead of your VPN. However, even if you had a VPN, if it's a government agency then generally speaking they will be able to find you anyways. A VPN doesn't "hide" you. It's not meant to. If you want to stay anonymous, there are several methods that can be utilized. The most obvious one is not connecting to the internet from your own home. Use the Starbucks WiFi. A more clever method would be buying slave bots and using poorly secured wifi netowrks around them to hop over one. Assume VPN connections are from companies based in countries not on friendly terms with yours. Like China/U.S. User -> RandomWifi -> VPN/SSH -> Slave -> SecondSlave/WifiHop -> VPN/SSH 2.0 -> Tor -> Market This is a very basic set up. I would personally add more to it with other stuff, but it all depends on your threat model. Small note. This assumes you're actually setting up your VPNs, not buying some "VPN service." I saw you wrote about being careful with VPNs and how "trustworthy" they are. I'm not sure why you would ever use a VPN service.