The rising popularity of digital applications, such as social networking, media share sites, and blogging, has significantly affected how medical trainees interact with educators, colleagues, and the public. Despite the increased popularity and use of such applications amongst the current generation of trainees, medical educators have little evidence or guidance about preventing misuse and ensuring standards for professional conduct. As trainees become more technologically savvy, it is the responsibility of medical educators to familiarize themselves not only with the advantages of this technology but also with the potential negative effects of its misuse. Professionalism, appropriateness for public consumption, and individual or institutional representation in digital media content are just some of the salient issues that arise when considering the ramifications of trainees' digital behavior in the absence of established policies or education on risk. In this commentary the authors explore the rising use of digital media and its reflection of medical trainees' professionalism. To address possible issues related to professionalism in digital media, the authors hypothesize potential solutions, including exploring faculty familiarity with digital media and policy development, educating students on the potential risks of misuse, and modeling professionalism in this new digital age.