The Tailored Response Test (TRT) is an innovative approach for evaluating higher cognitive processes. This study was designed to assess its value as a learning device. Two Objective Structured Clinical Examination (OSCE) stations assessed formulation of a differential diagnosis of abdominal pain: a Patient station and a TRT station. The order of the two stations for each student was varied in a double-blind crossover design. Students who had the TRT first scored significantly higher overall on the Patient station (mean = 42 ± 6) compared with students who did not (mean = 38 ± 8, p = 0.001 level), and were able to generate a broader differential diagnosis. These results suggest that the TRT, which involves active cognitive processing, had a positive effect on learning. This study supports its use as both an evaluation and a learning tool. Further studies are needed to determine the mechanisms in the TRT which produce this effect.