The use of walking workstations in educational and work settings has been shown to improve cognitive abilities. At the same time, it has been repeatedly shown that medical residents around the world do not meet exercise guidelines, mainly due to a scarcity of available free time. Our study investigates the boundaries of the previously observed phenomenon of improved cognitive performance with physical activity using materials that represent real life tasks. Participants had different level of expertise and involved second year psychology students, medical students, and family medicine residents. We examined the effect of being physically inactive (i.e., sitting) or active (i.e., walking) while diagnosing multiple complex presentations of four skin conditions. We assumed that being physically active, irrespective of the level of expertise, will bolster diagnostic performance. Our findings show, however, that being physically active does not change the performance level of participants with different levels of medical expertise. Implications for medical education and suggestions for further research will be discussed.