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I am going to use Tails to connect to Tor through VPN which has AES-256 data encryption, SHA-256 data authentication and RSA-4096 handshake encryption on my Mac on my school's WiFi (as public as I can get).

Is there anything I can do to make it more anonymous and make it so that no one can trace me back? Maybe I could have a program that bounces my IP address across servers, etc.

Edit: my school does not required log in, it does not have any password either. I have 4 other Facebook account none of which uses my real name.

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  • I agree with the answers given, when you connect to your school's network if you have to enter a login specific to you then that's a vulnerability, I guess a public hotspot isn't an option for you? McDonalds usually a offers reliable and anonymous internet connection
    – Purefan
    Jul 31, 2015 at 7:53

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Even if Tails offers anonymity and coming with default built-in encryption suites for different purposes, your anonymity is already compromised since as in all schools/universities we find the same policy: to use their WiFi they need to be sure you are either a student, a teacher or an authorized person to access their Wifi.

Also you must remember that Tor browser as well as the whole Tails operating system privacy-protecting flaws show that no anonymity system is fail-safe: you need to keep yourself Tails/Tor up-to-date to security issues as mentioned in this recent May 2015 report where it is stated that when it comes to anonimity:

there is no magic or perfect solution to such a complex problem.

Some vulnerabilities listed from that report:

  1. Tor exit nodes can eavesdrop on communications
  2. Tails makes it clear that you are using Tor and probably Tails
  3. Man-in-the-middle attacks
  4. Confirmation attacks
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There are two general categories of vulnerability to your anonymity that I would be concerned with given that setup:

  1. Using web sites that identify you (it's a moot point if you then go log into Facebook with your real name!)

  2. Traffic analysis - if your school requires login info specific to you, then the school knows who's sending the traffic, and if they can trace it back to your school via traffic analysis, they might request your identity from the school ('they' being the government in my mind). Same could possibly go for your VPN, if they're cooperative with the government.

There may be other zero day exploits that could de-anonymize you, but you'll always have that risk. The best defense against that type of thing will be making sure you use the most updated versions of the software you're using, especially tor.

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    Even if no one can trace back your location, you can still be only pseudonymous instead of anonymous if you can be associated with an identifier (a cookie in the simplest case). Have a look at Do not confuse Anonymity with Pseudonymity on Whonix' wiki.
    – ComFreek
    Jul 31, 2015 at 8:30
  • That's a good point. I didn't mean to imply that it's completely safe to log in to other services. When properly configured, though, TAILS and tor browser bundle should retain no data such as cookies after shutdown, and should have a minimally identifiable browser fingerprint, so later connection to a real identity should be fairly difficult.
    – childofsoong
    Jul 31, 2015 at 8:41
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You are putting all your internet traffic into the VPN's database thus putting a lot of trust into this company. That being said, I assume you aren't running a drugs, terrorist or child porn website on the dark web? The level of security you are talking about needing is overkill. I would personally connect Tails through a bridge or just run the VPN and keep a somewhat decent internet speed.

The Facebook part could, in theory, identify you if you have logged into any of these 4 accounts on an insecure network in the past.

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