Purpose: This study aimed to evaluate the effectiveness of role play to train medical students in history taking, problem identification and problem synthesis, and to assess whether the use of patient-educators as simulated patients enhances student learning outcomes. Method: This study adopted a mixed method two-armed quasi-experimental study design. In the 2012-13 academic year, all 180 third year medical students at the University of Hong Kong participated in the Problem Solving Workshop during the Family Medicine rotation. Students were randomly assigned into two groups: the intervention group had four simulated patients role playing their own clinical cases whereas the control group had workshop facilitators role playing the same cases. Before and after the workshop, the students watched a videotaped clinical consultation and completed a Medical Record Form. Students paired up to role play as a doctor to take a history, then they received feedback from the patients and provided feedback based on the learning experience and approach. Student performance on the end-of-rotation Objective Structured Clinical Examination (OSCE) was compared between the groups. Results: The quantitative results revealed statistically significant increase in the total score of Medical Record Form in both groups after the Problem Solving Workshop. Although both settings were proved to be effective, students valued the real patient interaction and the constructive feedback from patients. Their performance on OSCE showed no difference between the two groups. Conclusion: The Problem Solving Workshop had significant positive impacts on students’ ability to problem solve and problem identify. Role playing clinical cases either with simulated patients or facilitators is a promising approach for medical students to develop practical skills. Involving patient educators as simulated patient seemed to promote communication skills. Future workshops should increase student exposure to patient educators in practical training.