Abstract: The spread of digital communication in the employee–supervisor exchange relation has increased the risks of blurred boundaries between life domains and, subsequently, the need for work–life supportive supervisor behaviors (WLSSB). However, media richness and social presence theory indicate that WLSSB is simultaneously at risk because close bonds with supervisors are more difficult to develop and challenges in integrating work and personal life are more difficult to be signaled and understood. Following social network theory in the argument that it is not only the characteristic of the medium that is of importance but also the social embeddedness of its use, this research asks to what extent the association of digital communication with one’s supervisor and perceived WLSSB is context‐dependent. The overall results based on the European Social Survey (round 10) reveal that in‐person communication is more strongly associated with WLSSB than digital communication. However, more nuanced investigations suggest that this is not necessarily driven by the richness of the mode of communication. We find that the meaning of digital communication with one’s supervisor gains importance in size and significance (a) where it complements seldom in‐person communication, (b) where the organizational norm of high work devotion is weak, and (c) where work–life supportive state policies are pronounced. We conclude that the implications of digital communication for WLSSB are dependent on the centrality of digital communication in opportunities for the exchange of WLSSB and dependent on supervisors’ interest and agency to enact WLSSB in digital work communication.