Defensive Design by 37 Signals and Don't Make Me Think by Steve Krug are both great books about how to design for when things go wrong. Engineers, in addition t

Defensive Design by 37 Signals and Don't Make Me Think by Steve Krug are both great books about how to design for when things go wrong. Engineers, in addition to designers, should read these books post-haste. EDIT: If you're a hacker in SOMA/SF and want to borrow either of these books they're very quick reads. The trouble with technical error messages is that almost invariably, engineers end up writing them. "Not my area of expertise" or "I put in a request for copy months ago" are some of the many reasons that poor error handling happens. Additionally, having a truly helpful environment requires additional resources: In the example in this article, the "Heres how to fix your problem!" link would require an additional application to keep track of known issues and solutions. That being said, it's exactly how every application should work: Error messages like this may not be daunting to more technically proficient users, but the vast majority of users are not technically proficient and many users simply give up (if they can) when they see an error message that they are unable to understand/fix.