In the Beginning was the Command Line by Neal Stephenson: An intelligent essay dealing with the trials and tribulations of computer Operating Systems. Of course one of the big problems he discusses is Metaphor Shear (which is basically the point at which a metaphor fails), which is ironic because he uses quite a few metaphors himself in the essay. One of the best is when he relates the Hole Hawg (an incredibly powerful drill that with drill through just about anything, but also incredibly dangerous because it has no limitations or cheap safeguards to protect the user from themself.) with the Linux operating system. The essay is a great read, and goes into much more than just Operating Systems. Highly recommended.
If you like Stephenson’s fiction, you might also want to check out The Great Simolean Caper, an interesting story set in the not to distant future. It shares some common ground with Stephensons other work (namely, Snow Crash) and is quite an enjoyable read. Its also a bit scary, because it brings up quite a few security and privacy concerns. With the advent of digital cable and set-top boxes, companies are starting to track what you are watching on television, whether you like it or not. I’ve seen the data myself, and I think the advertising industry is going to go wild when these numbers start piling up (the data I saw showed enormous spikes and troughs roughly coinciding with commercials). The sneaky set-top boxes in Stephenson’s Caper might seem unlikely, but we’re really not too far away from that right now…