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Across the globe, the increasing exploration of women entrepreneurship as an emerging phenomenon has resulted in growing lines of examination that extend across the motivations, challenges, contributions, and strategies for navigating the entrepreneurial space. Despite such advancements in the field, the effects of gender and motherhood on entrepreneurship remain highly under-theorized and under-contextualized, with little appreciation of the spatial and situational realities that they confront. Such is the case for the Caribbean where women and mothers are increasingly entering into entrepreneurship, but where their realities are yet to be understood. In this chapter, we therefore make a case for the use of contextual theorizations that focus on the structural, historical, and cultural aspects of entrepreneurship, and the implications of these for the thinking and action of women entrepreneurs and mumpreneurs in the region. Implications for entrepreneurial research, policy, and practices in the Caribbean are also discussed.