Objective: The effects of off-task media use in academic settings on academic performance have been widely reported. In response, a range of interventions have been proposed. Among these have been calls for the cultivation of more effective self-regulation of media use. Against this backdrop, the present study investigates students' self-regulation of off-task media in academic settings. Method: A series of focus groups was conducted involving 30 undergraduate students at a large, South African university. A combination of inductive and deductive analysis was conducted on the basis of prominent theories of self-regulation. Results: The presences of off-task media in academic settings create ongoing experiences of goal-conflict and many students become trapped in cycles of repeated self-regulation failure, ultimately culminating in procrastination. Conclusions: We refer to this phenomenon as the media procrastination cycle and argue that it contributes to negative affect, stress, and anxiety among students.