People do not want to talk about failure, and technological innovations that do not work out are especially difficult for librarians to discuss. Technological failures are expensive in terms of money and time lost, and they are often minimized by library directors in their annual reports in favor of reporting more positive outcomes. Today's million-dollar question about technological innovation in libraries is whether the new Library 2.0 technologies are winners or bloopers. Are the so-called "social technologies" of wikis, blogs, Facebook, YouTube, and virtual worlds such as Second Life right for libraries? In this article, the author presents three scenarios of technology innovations in libraries that have gone wrong. She also presents issues to consider before and after innovating. and suggests paying close attention to the lessons of the past in order to minimize the risks of technology innovations.