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Research indicates that many children in the Caribbean live apart from one or both parents due to migration to developed countries (UNICEF, 2023). This migration often results in transnational living arrangements, where children are left behind in their native countries while their parents live abroad. This separation places parents in a unique role where child-rearing responsibilities are often left to the caregiver in the country of origin, such as grandparents, aunts, and other extended family networks. The current study seeks to understand how parents living abroad navigate the discipline of their children. In this study, we conducted in-depth interviews with N = 10 parents (3 Males; 7 females) from Jamaica and Trinidad and Tobago. We identified recurring patterns within the reflections using thematic analysis. The findings highlight the significant challenges parents encounter in maintaining disciplinary roles across geographical boundaries. Specifically, parents express their struggle to communicate and discipline their children effectively due to their physical absence. Consequently, they rely on caregivers to assume the disciplinary responsibilities in their absence. This study contributes to academic discourse by deepening our understanding of how migration intersects with parenting and child development in diverse cultural contexts.