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I want to be as anonymous as possible online without anyone being able to connect me to my online activity. Assume that the people trying to track me have lots of resources and can even use the legal system against me. In essence, assume the United States Government is trying to track me.

I know Tor and VPNs provide anonyminity. Will the combination of these protect me? Would someone be able to find my VPN from Tor, and then from the VPN find me? Or am I actually secure? Can I remain anonymous from the government of the United States of America?

This question has an open bounty worth +150 reputation from Conor Mancone ending in 6 days.

The question is widely applicable to a large audience. A detailed canonical answer is required to address all the concerns.

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    When you use a VPN your VPN provider knows your 'real' IP address. Apart from that the anonymity depends largely on your actions. E.g. if you go to google.com and log in with your google account during your 'anonymous' session, then at least Google will know who you are and can track some of your actions. Also if you use a browser that can be fingerprinted then it will be possible to profile you in some way. If you are unlucky enough to use a compromised Tor exit node, then the additional VPN will give you some extra protection (e.g. noone can see your IP address). – Martin Fürholz Jun 20 at 1:32
  • The short answer is going to be that there's no such thing as 100% security. There's always going to be a chink in your armor. Even if this layer is secure, you always leave traces of your activity that can potentially tied back to you. – Steve Sether Jun 20 at 15:08
  • There's no such thing as total security. – Tobi Nary Jun 27 at 7:06
  • Snake, I've edited your question fairly heavily. As you may have gathered from comments there is no such thing as 100% security. My goal with my edit is to still get your question answered, while avoiding the kind of assumptions that will make it hard to get food answers. If you don't like my edit you can revert it. – Conor Mancone 11 hours ago
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If you're serious about it, you could look into installing Qubes as your main OS, and running Whonix in one of the Qubes.

Qubes was a project started by Joanna Rutkowska (who developed the idea of the Blue Pill virtualisation rootkit).

Qubes takes an approach called security by compartmentalization, which allows you to compartmentalize the various parts of your digital life into securely isolated compartments called qubes.

...and...

Whonix is based on Debian and Tor and utilizes two VMs, a “gateway” and a “workstation”. Qubes security architecture makes use of Whonix’s isolation by using the gateway as a ProxyVM to route all network traffic through Tor, while the workstation is used for making AppVMs.

Between the two of those (and some reading around common mistakes as mentioned by @Peter Harmann) might see you as best protected as possible.

[Edit] To further the answer, to potentially address issues raised in the comments regarding advice, there are some discussions raised over on tor.stackexchange which might add some clarity:

Comparison of Whonix and Tails Threat model that Qubes is most appropriate for (including an answer from a whonix maintainer)

  • Any reason why qubes instead of Tails? For most purposes, Tails should be a better choice for anonymity IMO. I did not give a recommendation on purpose, as I am not able to list all the caveats and partial advice here could be worse then no advice. – Peter Harmann Jun 20 at 15:04
  • Could run Tails on top of Qubes. I accept your point of recommendations being potentially fraught. – Ian Jun 20 at 15:13
  • So you have a suggestion for anonyminity, and say that it is probably your best bet. However, I feel that it still leaves the main question unanswered: will this secure a user from tracking by an adversary as well-resourced as the US government? After all, if this still gets you de-anonymized after just a week, then it really doesn't help. – Conor Mancone 11 hours ago
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No. Just installing Tor and a VPN does not make you safe. Even if Tor was resilient against attack and VPN was secure and trustworthy, they would only mask your IP. Many people using Tor were caught, not because Tor was defeated, but because they made a mistake. They logged in to a social network or used it on a school computer or had cookies in their browsers or allowed javascript/adobe flash player to reveal their IP and many more. Being completely anonymous against the government of the United States is an open problem. Even if there was a way, there would be no way to show, if it really works or not.

  • Also the window should be locked and the size should be set to a random size at the time of startup (not max). – tungsten 13 hours ago
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    @tungsten random window size? I feel like that makes you more trackable, not less. The goal is to look like everyone else, not to stick out – Conor Mancone 11 hours ago

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