Two studies examined relationships between leaders' and subordinates' attachment orientations emotion regulation capabilities and affective experience and satisfaction at work. As expected supervisors' and subordinates' insecure attachment orientations (higher anxiety and avoidance) were associated with own positive affect and satisfaction at work. Supervisors' anxious attachment orientation was associated with subordinates' lower positive affect and satisfaction at work. Contrary to hypotheses supervisors' higher avoidance was associated with subordinates' lower negative affect and higher job satisfaction. Supervisors' emotion regulation capabilities did not mediate relationships between supervisors' insecure attachment orientations and supervisors' own or subordinates' affect and job satisfaction as expected. However subordinates' emotion regulation capabilities interacted with supervisors' attachment orientations to predict subordinates' emotion experience at work. The results contribute to an understanding of attachment orientations' emotion dynamics in leader–follower interaction pointing in particular to perceptual and affect-related processes at different levels of analysis.