Or “How to be unpestered”.

Its important to bear in mind that there might be various types of pestering to avoid…

• real-time activity monitoring over the internet
• other people taking advantage of anonyminity and pretending to be you
• physical computer capture and analysis

Think of avoiding:

• arousing suspicion
• proof of suspicious activity
  • an encryption program on your computer could be considered such
  • likewise if your computer appear totally empty it may equally arouse suspicion

• Gaim is the useful program here - can use encrypted jabber for a start
• Off-the-Record messaging

You want to use GnuPG for encryption, with the Enigmail plugin for Thunderbird Note that GnuPG can do more than email encryption

See Internet Privacy at wikipedia. This has links that explain this. An example of a system is Tor

You may wish to hide certain local data. Ideas to do this include:

• encrypted filesystems (but then you need to use a password to access them, may be hard to hide)
• wiping data off your disk (note that simple deletes often leave lots of stuff around)
• consider not just documents, but web history, etc

I think a good idea is to keep an offline backup in a region that is not under suspicious control. You need a good fast backup system. And then a way to delete data quickly and securely if required. But don’t neccessarily delete everything, as that might be suspicious

An alternative if connectivity is good is to use an offsite file system that you can save things to, so they are never on your local disk.

For encrypted file systems see

• TrueCrypt for Windows, which looks really good (it hides stuff well too)
• FreeOTFE for Windows, which can share encrypted volumes with Linux (also hides stuff well) - with SecureTrayUtil you can unmount your encrypted volumes with a hotkey