The present study contributes to the conversations on the role of ‘autonomy supportive’ factors in employee wellbeing in remote work contexts by examining the relationships between servant leadership, communication frequency – overall and via synchronous (i.e., individual video-calls, individual telephone calls) and asynchronous communication channels (i.e., e-mail messages, and WhatsApp) – on the one hand, and job satisfaction, on the other, and the moderating role of generation (Baby Boomers and Gen X versus Gen Y) in these relationships.Method<jats:p/>Building on self-determination theory, incorporating insights from servant leadership, telework, and media richness and synchronicity literatures, we developed hypotheses that were tested via multilevel analysis (273 employees nested in 89 managers).Results<jats:p/>In line with expectations, servant leadership had a positive relationship with job satisfaction. Total communication frequency, however, was not related to job satisfaction. Further analyses per communication channel showed that only level 2 e-mail communication frequency was positively related to job satisfaction. In contrast to expectations, the relationships studied were not moderated by generation.Discussion<jats:p/>We concluded that, for all generations, both servant leadership and frequent (e-mail) communication can be regarded as ‘autonomy supportive’ factors in employee wellbeing. Paradoxically, whereas servant leadership, considered as a human-centric leadership style, suggests close trust-based employment relationships, employees valued frequent asynchronous communication (via e-mail). Having access to information and knowledge when needed may satisfy employees’ need for autonomy (and perhaps for flexibility to engage in work and non-work activities). The insights gained in our study can inform organizations, managers, and employees, particularly in future remote work contexts.