This study examines multitasking with media and technology among medical students across four learning contexts (lecture, lab, team-based learning, and homework) and whether stress moderates the relationship between multitasking and academic performance. The proliferation of technology simultaneously used for learning, entertainment, and socialization facilitates multitasking in learning environments. There is comparatively little research on multitasking behavior among medical students. Data were collected using a survey distributed online to four cohorts of an allopathic medical school to examine the relationship of multitasking and academic performance using both descriptive and correlational analyses of multitasking behavior in each of the four learning contexts. A moderation analysis was used to investigate the role of stress in this relationship. Lower multitasking was reported as learning contexts became more active (e.g., lecture versus lab). Some respondents, however, appeared resilient to the changing environment, maintaining high levels of multitasking. In the low multitasking environment of lab, respondents with high levels of stress, who multitasked heavily, reported better academic performance. Approaches to multitasking must account for learning environments and the individual propensities of students. Additionally, some forms of multitasking may not be counterproductive to learning, but the boundaries between productive and counterproductive multitasking are difficult to distinguish.