The landmark Institute of Medicine report on patient safety categorized inappropriate plans of care as a medical error. This broad classification encompassed decision-making errors by clinicians that included diagnostic errors but also the notion of contextual errors. The latter are those that occur because of inattention to patient context such as environment, behavior, economic situation, or access to care and social support. This study used unannounced standardized patients who acted out four clinical scenarios presenting with biomedical and contextual complicating factors. Attending physicians probed fewer contextual red flags than biomedical ones and provided error-free plans of care in 73% of the uncomplicated encounters, 22% of the contextually complicated encounters, and only 9% of the combined biomedically and contextually complicated encounters. The authors advocate for greater attention and performance metrics to assess how well providers deliver individualized patient care plans based on probed contextual factors.