The current study utilizes attachment theory to understand how leader–follower relationships impact emotional and behavioral outcomes in the workplace. Specifically, we examine the roles of two dysfunctional attachment styles – anxious and avoidant attachment – as determinants of trust in leaders, stress and citizenship behaviors. Results showed that followers with anxious attachment orientations reported experiencing more stress, whereas followers with avoidant attachment orientations were less likely to engage in organizational citizenship behaviors. Moreover, we found that the relationship between attachment orientations and workplace outcomes are mediated by affective and cognitive trust. However, these negative outcomes only occur when the follower has a leader with an avoidant attachment orientation. Implications for training, selection, job design and understanding leader–follower dynamics are discussed.