Pupil diameter is enhanced in a variety of emotional contexts, including viewing pictures, listening to sounds, and during threat of shock. In this study, we investigated pupil diameter changes during emotional imagery. Participants imagined scenes describing pleasant, unpleasant, or neutral events while pupil diameter was continuously recorded. Second by second changes in pupil diameter were analyzed to determine whether, and when, modulation of the pupil as a function of hedonic content is found. Results indicated a significant effect of hedonic content beginning shortly after script onset, with enhanced pupil diameter when imagining emotional (pleasant or unpleasant), compared to neutral, scenes. Pupil diameter during imagery covaried with rated emotional arousal, consistent with an interpretation that changes in pupil diameter during emotional imagery reflect sympathetic nervous system activity. Because emotional imagery is a key element in clinical assessment and treatment, pupil diameter could prove a useful index of emotional engagement in a variety of clinically pertinent contexts.