Challenging stressors have been positively linked to various work outcomes. However, the role of individual differences in stress appraisal in shaping the function of challenging stressors and work outcomes has been rarely discussed. Drawing on the individual differences perspective, the authors propose that employees higher in challenge appraisal are more likely to have challenging stressors and are more responsive to such stressors to have a higher positive affect at work. Results obtained from 117 employees supported the hypotheses. The results indicated that challenge appraisal is positively related to challenging stressors. In addition, challenging stressors has a positive association with positive affect at work when challenge appraisal is high but has a null association when challenge appraisal is low. The findings suggest that challenging stressors does not necessarily bring positive work outcomes as suggested in past studies and highlight the importance of considering dispositional tendency in stress appraisal when looking into the function of challenging stressors and work outcomes.