This article presents the findings of a retrospective review of medication errors made and reported by nursing students in a 4-year baccalaureate program. Data were examined in relation to the semester of the program, kind of error according to the rights of medication administration, and contributing factors. Three categories of contributing factors were identified: rights violations, system factors, and knowledge and understanding. It became apparent that system factors, or the context in which medication administration takes place, are not fully considered when students are taught about medication administration. Teaching strategies need to account for the dynamic complexity of this process and incorporate experiential knowledge. This review raised several important questions about how this information guides our practice as educators in the clinical and classroom settings and how we can work collaboratively with practice partners to influence change and increase patient safety.