Abstract Organizational efforts at monitoring employee activity must be perceived as respecting privacy and fairness. However, even when monitoring systems are designed to do so, employees might not be willing to accept and use monitoring technologies. This study examined whether personality moderated the relationship between workplace monitoring system characteristics, fairness, privacy and acceptance. Six hundred and twenty-two participants were asked to provide their assessment of an awareness monitoring system (that determines employee availability to interact with geographically distributed colleagues) and to complete a five-factor measure of personality (i.e. extraversion, agreeableness, emotional stability, openness to experience, and conscientiousness). Results indicated that emotional stability and extraversion altered the relationships between the paths in a model of monitoring acceptance. Specifically, people who scored lower in extraversion and emotional stability were less likely to endorse positive attitudes toward monitoring, even with privacy and fairness safeguards in place. Implications for the expansion of models of workplace monitoring and for the practice of monitoring in organizations are discussed.