This review examines the extent to which undergraduate prescribing education prepares graduates for the complexities of prescribing in the workplace context. In order to prescribe safely, it is important for medical students to acquire prescribing expertise. We have developed a theoretical model, based on theories of expertise development, which acknowledges the inherent complexity of the task itself, the social context and the relationship between the two. We have examined the empirical evidence on educational interventions for prescribing by reviewing the extent to which the interventions acknowledge the different components of our theoretical model. Fifteen empirical studies met our inclusion criteria and were reviewed in detail. All the studies were conducted between 2002 and 2010, six were controlled trials, six were before and after studies and three were prospective observational studies. We found that most studies focused on improving and evaluating students' knowledge and skills, although they used different approaches to doing so. These aspects of prescribing only constitute a small part of our theoretical model of prescribing expertise. Other important components, such as social context, metacognition and training transfer, were neglected. We suggest that educational interventions need to account for the integrated nature of learning to prescribe and take a more contextualized approach which considers the task as a whole, rather than isolated constituent parts. In doing so, prescribing education could equip graduates with the necessary expertise to judge and respond to situations, enabling them to prescribe safely, or seek the help to do so, in the unpredictable and complex context of workplaces.