This paper builds on the influential work of Suzan Lewis examining how employees’ work–life experiences are shaped by different layers of context. Our approach is therefore a comparative one using data from four organizational contexts in two countries, the Netherlands and Slovenia. Within each organization, we examine the role of different types of supervisory support (specific family support and general support) and the quality of the relationship between supervisor and subordinate (LMX) in work-to-family conflict, enrichment, and work–life balance satisfaction. Findings indicate that in a context with a high level of national policy support, some dimensions of family support are seen as part of general supervisory support. Moreover, the role of supervisory support and the leader–member exchange relationship differs between organizational contexts and the outcomes considered.