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bbb

Hypothetically, it is really easy get away with something like this:

1) Go to a well-trafficked coffee shop that you've never been to before. Pay with cash.

2) Use a bootable Linux CD or a virtual machine for the actual "attack." (Xen, VMWare, anything.)

3) Spoof your wireless MAC address. (if you are paranoid)

4) Perform your "special investigation." Post your info to wikileaks.

5) Reboot without the Linux CD or securely delete the virtual machine when you are done.

6) Don't brag about it.

See, you don't even need a proxy. It's not that hard.

How can anyone be so stupid to get caught anyway?

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1.5) ensure the coffee shop has no security cameras

Good point.

But if there are a lot of laptop-using customers even a security camera shouldn't be too much of a problem. After all, just being there is not a crime in itself. And wiping your system will delete all evidence that could link you to any log files.

Or devise some system that can autonomously sniff from inside a laptop.

Even better, use a tiny embedded Linux device like gumstix (http://www.gumstix.com/). You could even hide it somewhere and leave, let it do it's thing, and either pick it up later, or have it transmit it's findings to you over the net (through some anonymous proxy, of course)

And this is why SSL is important.

Just don't go inside the coffee shop. Do it from a car or the restaurant next door, just to be safe.

Or better yet, drive down the road looking for a resident with an unprotected WiFi connection.

If you are going to go into town anyway, why not just go to the library and use their computers?

Because the library is more likely to have their computers controlled tightly: they may keep a record of who requested to use a computer, use some kind of logging proxy, keep a copy of your ID, and you leave finger prints etc.

Also, a library may not let you install the tools that you need. If you bring your own laptop then you can do whatever. Also, a busy coffee shop offers more anonymity than a library most of the time.

Additionally, explaining why you went to a coffee shop may be easier than explaining why you went to the library (if you are like most people). Having to explain why you diverted from routine is what gets you caught.

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