Negotiating work and children can compromise the wellbeing (Gatrell et al., 2017) and academic trajectory of mothers (Guarino and Borden, 2017). In the context of the academy, academic mothers are often challenged by the lack of institutionalized systems of support to cushion the effects of competing tasks, efforts, and agendas across work-family domains. With heightened levels of gender inequalities for women academics, the “systematic failure to recognize the ways that motherhood can alter a female academic’s career in profound ways” remains an area of contention and for intervention (Castenada and Isgro, 2013, p. 9). Yet, there is little empirical literature that seeks to both locate and trouble the structural and situational forms of precarity for academic mothers within the Caribbean, the subjectivities that are formed through these experiences, and the implications of these for promoting issues of equity and diversity. The paper uses matricentric Caribbean Feminist approach and narrative inquiry to draw on the stories, challenges, and strategies for navigating academic mothering. Through this examination this chapter assesses the status and scope of scholarship on academic mothers in the Caribbean and connects this to global scholarship to demonstrate the need for contextualized understandings of and interventions.