Since technology is so expensive, making the wrong purchasing decisions can have severe financial consequences. The purpose of this article is to describe three technology decisions that failed to achieve their original intent. For each of the three, the author's discuss the expectations of the chief information officer, the vendor's sales pitch, why the product was chosen, what went wrong and why, and the lessons that were learned. The article concludes by suggesting ways to minimize these sorts of costly technology decisions and by describing how students found ways to make the most of technology gone awry.