How can we explain the crossover of positive experiences from supervisors to their subordinates? Drawing on crossover research and social learning theory (SLT), our main goal in this study is to explore mechanisms and boundary conditions to understand how positive crossover occurs from supervisors to their subordinates. We focus on the nature and foundations of positive crossover in the domains of work and home, and explore the downstream consequences for subordinates’ domain-specific outcomes. Using matched supervisor–subordinate data, the results of multi-level analyses demonstrated that perceived organization support (POS) of subordinates does not impact the positive association between supervisors’ and subordinates’ work engagement. However, family supportive supervisor behaviours (FSSBs), as perceived by subordinates, strengthen the positive association between supervisors’ and subordinates’ home engagement. Importantly, subordinates’ work and home engagement explains why supervisors’ state of engagement in work and home domains, respectively, influences subordinates’ functioning in work and home domains, underscoring a trickle-down model. We contribute to crossover research through demonstrating that crossover occurs from supervisors to their subordinates in work and family domains. Firstly, we highlight the role of relational mechanisms as boundary conditions of crossover process. Secondly, we extend the understanding of how crossover impacts on subordinates’ key outcomes at work and home. Thirdly, we expand crossover research in an understudied context, Chile. In doing so, we contribute to the literature on hierarchical market economies, through providing further insights on the operation of interpersonal ties and relations in such contexts.