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Assuming these steps are done, what else can be done to get a maximum of anonymity

  • Use a VPN like ZenMates chrome plugin so your public IP is obfuscated
  • Use an alternative DNS server so official ISP can't log web queries (VPN connections)
  • Use anti-tracking tools like Ghostery or AdBlock (e.g no Facebook button for logging visited sites)
  • Use HTTPS over HTTP if possible (HTTPS everywhere extension)
  • Disallow third-site cookies and delete all cookies after browser exit (flash cookies are still an issue)

Questions:

  • What can a geek do to live anonymous? (Like trashmail or multiple online pseudonyms)
  • What about a secure mail provider who stores all mails encrypted? (end-to-end encryption with PGP isn't practical yet since my receiving friends/coworkers refuse to use it)
  • Can I defend myself against fingerprinting me through browser characteristic identification (combination of User Agent, screen resolution, browser plugins, time zone and fonts)
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The one thing you did not tell us is the most important piece, "protect your privicy from whom?". The steps you do to keep your activity secret from your sister is different than the steps for keeping your activity secret from your ISP. Also you need to define "privacy", if you make two visits to the same site do you care if the site knows "the same person" visited twice (even if they can't tell who that person was)? –  Scott Chamberlain Aug 10 '13 at 22:34
    
Good point. Lets assume its the ISP to protect from. (Can't answer your second question.) –  nixda Aug 10 '13 at 22:43
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If all you care about is the ISP then you need VPN/proxy and nothing else (If you are worried about the VPN/proxy's ISP too Tor might be a good choice of proxy) . the ISP can't see what is in your vpn tunnel so everything else on top of that is not necessary. –  Scott Chamberlain Aug 10 '13 at 22:48
    
That goes in the wrong direction. Think of the term privacy in a more general way. There are different organisations/companies who are tracking and storing everything they can about visitors. –  nixda Aug 10 '13 at 22:51
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Ok, then you are not trying to protect yourself from your ISP you are tring to protect from tracking compines. See why I said it is important to specify "from whom" a solution for protecting from ISP does nothing to protect from tracking companies. I would reccomend changing your first question to have a specific "threat model" to get good answers on it, clearly explain who you are trying to stop and exactly what you are trying to stop them from doing. –  Scott Chamberlain Aug 10 '13 at 22:52
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2 Answers

Your first question is subjective and there is no "right or wrong" answer so I am going to skip over that.

If "the government" is who you are trying to protect yourself from then secure mail providers are pointless. If the provider can decrypt it to send the email to you then they can be court ordered to decrypt it and send it to the government too. Even if they could not decrypt it (say you use a custom client to read your emails and the private key is not stored on their server) they could be court ordered to start storing plain-text copies of every email you send out or receive (As you said end to end encryption is not possible for you) and hand them over instead

To defend your self from fingerprinting the best you can do is get a environment that has a common fingerprint that many people have, the only way to do that is boot off a popular Live CD distro and make no modifications to it (also be sure to not preserve any changes between reboots and reboot frequently, the more you use it the more likely "changes" will creep in making you unique). By doing that everyone else who also uses the cd and did not customize it will have the same fingerprint as you.

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@MichaelKjörling in the parentsis of the 2nd bulletpoint question: "What about a secure mail provider who stores all mails encrypted? (end-to-end encryption with PGP isn't practical yet since my receiving friends/coworkers refuse to use it)" –  Scott Chamberlain Aug 10 '13 at 22:45
    
Yes, I saw it after I posted my comment. Sorry. –  Michael Kjörling Aug 10 '13 at 22:46
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use TOR, https://www.torproject.org/ , which actually works against tracking. (probably government tracking).

just make sure you are allowed/legal to do so, FBI seems to particular hate them much.

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