Cyberloafing—a type of counterproductive behavior—occurs when employees use the internet for personal use while at work. Past research shows that work role stressors (i.e., role conflict, role ambiguity, and role overload) and Big Five personality traits (i.e., neuroticism, conscientiousness, extraversion, and agreeableness) predict cyberloafing, but research has yet to explore interactions among these factors. The current study aimed to address this gap by examining whether work role stressors strengthen the relationship between personality and cyberloafing based on the Personal Resource Allocation (PRA) framework. In an online survey of employees from diverse occupations (N = 343), we replicated past work showing relationships among personality traits and cyberloafing. However, role conflict was the only stressor that predicted cyberloafing. Moderated multiple regression analyses suggested only three statistically robust findings in the expected direction: role conflict strengthening the positive association between neuroticism and cyberloafing, role conflict strengthening the negative association between agreeableness and cyberloafing, and role overload strengthening the negative association between conscientiousness and cyberloafing. Overall, this study implies mixed and somewhat weak support for PRA framework predictions, including a lack of consistency in a specific role stressor enhancing personality-cyberloafing relationships. Practical implications for personnel selection and employee training/development are also discussed.