Two studies were conducted examining the interactive effects of chronic pain, perceived perfectionism (e.g., self- and socially prescribed), and guilt on job tension and job satisfaction. It was hypothesized that chronic pain would have its most adverse effects on these work outcomes when concurrently coupled with high levels of perceived perfectionism and guilt. In both studies, the results supported the interaction effect of Chronic Pain × Socially Prescribed Perfectionism × Guilt on tension and satisfaction in the expected direction. As predicted, the results also indicated a Chronic Pain × Guilt × Self-Oriented Perfectionism interaction on job tension. Implications for theory and practice, strengths and limitations, and avenues for future research are provided.