While medical education has remained relatively constant over the past century, the rising popularity of internet-based technologies, such as applications for social networking, media sharing, or blogging, has drastically changed the way in which physicians-in-training interact with educators, peers, and the outside world. The implementation of these new technologies creates new challenges and opportunities for medical educators. Representation, the absence of established policies and legal precedents, and the perception of the lay public exemplify some of the issues that arise when considering the digital images used by trainees. While some of these issues affect higher education generally, medical schools are faced with additional challenges to ensure that graduates exemplify the ideals of medical professionalism. We present a case vignette with subsequent discussion to highlight the complexities of ensuring medical professionalism in the digital age.