Whether or not you use a Live OS, make sure the OS doesn't store information that can be used against you. If you're not using read-only, bootable media, consider using a VM solution that resets itself after every use. Better yet, do both. Use a Live OS stored in a VM. Let the VM assign random DHCP and ARP addresses on every start.
3. Connect anonymously
Next, you'll need to connect to the Internet using an anonymous method. The best approach would probably be to jump around random, different, open wireless networks, public or otherwise, as much as possible, rarely repeating at the same connection point. Barring that method, you would probably want to use a device built for anonymous wireless connections, like ProxyGambit. I'll let ProxyGambit describe itself:
ProxyGambit is a simple anonymization device that allows you to access the Internet from anywhere in the world without revealing your true location or IP, fracturing your traffic from the Internet/IP through either a long distance radio link or a reverse tunneled GSM bridge that ultimately drops back onto the Internet and exits through a wireless network you're no where near. While a point to point link is possible, the reverse GSM bridge allows you to proxy from thousands of miles away with nothing other than a computer and Internet with no direct link back to your originating machine.
4. Use Tor
Whatever Live OS and Internet connection method you use, make sure to go with an anonymizing browser, such as a Tor-enabled browser. Tor is actually an entire system -- tools, browsers, APIs, and network -- dedicated to helping you and your connection remain anonymous.
Once you enter a Tor network path, the traffic to and from your destination will be routed through a random set of "Tor nodes." Although Tor's anonymity can be defeated, it remains one of the best ways to stay anonymous when combined with these other recommendations. You can even buy hardware-based Tor solutions like Anonabox.
5. Don't use plug-ins
It's very important to remember that many of today's browser plug-ins, particularly the most popular ones, leave clues that reveal your identity and location. Don't use them if you want to preserve your anonymity.
6. Stick with HTTP/S
Don't use any protocols other than HTTP or HTTPS. Typically, other protocols advertise your identity or location. When working with HTTPS, use only handpicked, trusted certification authorities that don't issue "fake" identity certificates.
7. Avoid the usual applications
Don't install or use normal productivity software, like word processors or spreadsheets. They, too, will often "dial home" each time they're started and reveal information.
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