(If you can't get Tails to boot on your Windows or Mac PC, many of the security applications included in Tails can be installed individually on Windows and OS X systems.)
Once you've got it going, you'll find that Tails' default desktop is the popular GNOME Linux desktop. If you (or your users) aren't comfortable with GNOME, Tails can masquerade as the more familiar Windows XP.
Two types of security
Online security has always been difficult to achieve because the Internet is built on open protocols and wasn't designed for anonymity or encryption. It's easy for anyone with access to the routers, servers and wires that handle Internet traffic to track a user's activities and eavesdrop. Ordinary system and network administration tools, such as packet sniffers and network debuggers, can see and record your location, the sites you visit, the contents of emails, instant messaging conversations and file transfers, and capture cleartext passwords.
Tails offers two types of protection: anonymity and encryption.
Anonymity is the more difficult of the two. If you want anonymity, you need to foil traffic analysis — analysis of the trackable metadata that Internet routers require. Tails does this by routing your Internet travels through a service called Tor (which stands for The Onion Router).
Tor, which was invented by the U.S. Naval Research Laboratory for protecting government communications, is a distributed, anonymous global network of routers that steers your Internet workings through a twisty chain of encrypted TCP connections. Each link in the chain knows only about the links that it connects to: the previous links and next hops. No single relay knows your whole data path. Tor also gets around any Internet fences or roadblocks. It is available for anyone to use and is maintained by a global community of volunteers.
As cool as this is, it has some weaknesses. It's slower than unprotected Web surfing, which is an inevitable consequence of taking a devious path to your online destinations. This is mitigated to a degree because Tor keeps you on the same route for 10 minutes, and then randomizes you to a new one.
In addition, Tor might not foil traffic analysis by any entity, such as a government, that has the resources to capture and analyze traffic globally. And keep in mind that, while Tor is beneficial for everyday Web surfing and online shopping because it foils traffic analysis and user profiling, as soon as you log into anything, you've given up your identity to whatever degree the site protects, or shares, user data.
But the biggest technical weakness in Tor is exit nodes. Tails has a warnings page with a diagram showing how this works. In a nutshell, eventually your packets have to leave the Tor network on the last hop to your destination, and anyone running an exit node can easily snoop on your session. In fact, a researcher did this back in 2007 and collected an impressive amount of sensitive information.
Sign up for CIO Asia eNewsletters.