If I was a lawyer advising a client with a questionable criminal liability, or a person in absolute need of privacy, I’d recommend the following:
- Do NOT use free anonymity services such as TOR if you are transferring sensitive information. Countless persons in government and journalists across the world have made this mistake. Ever heard of WikiLeaks – they got their start by creating TOR end nodes and snooping data.
- Use a Live DVD like Amnesic Incognito Live System or Ubuntu Linux for anonymous browsing. It’s fairly simple to burn an Ubuntu DVD and to boot your laptop device from the DVD. The live system does not save any cache or browsing history to your hard disk.
- Use a VPN to transmit sensitive information. There are two VPN types – SSL VPN and IPSEC VPN. Either will do. I’d suggest subscribing to a VPN service whose infrastructure is hosted outside of the government’s reach. StrongVPN has host servers located in several friendly Caribbean nations.
- Use different anonymous proxy tunnels through your VPN if you plan to access a website or service regularly and wish to remain anonymous. These services have the same limitations as Tor though and shouldn’t be used for transferring sensitive information. I explain a bit more below.
There are countless SSL/TLS encryption schemes, countless SSL/TLS software implementations, and each configuration can be potentially distinguished depending on the application software stack, operating system, hardware, etc. in use. The permutations among these configurations is large enough to distinguish a browser client.