Health information technology is widely accepted to increase patient safety and reduce medical errors. The widespread implementation makes evident that health information technology has become of a complex sociotechnical system that is health care. Design and implementation may result in a failure; even health information technology can lead to adverse events instead of mitigating them. In this chapter seeks to outline the complexity of health information technology as a part of a sociotechnical systems, describes two failures at different organizational levels and presents a model how risks can occur. Unfortunately there is a mainly anecdotal knowledge about health information technology failure and potential adverse effects. Therefore the author suggests how as a first step proper and mandatory reporting can lead to better knowledge of failures of health information technology as part of a sociotechnical system and improve deployment in the coming years.