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ABSTRACT Objective This study explores the parenting experiences of transnational parents from three English‐speaking Caribbean countries: Grenada, Jamaica, and Trinidad and Tobago. Background While transnational parenting has been well studied in other contexts, research on Caribbean parents remains limited, underscoring the need for further exploration into the experiences of these families. Method Ten parents (six mothers and four fathers) participated in the study; all of whom self‐identified as immigrants from the Black English‐speaking Caribbean. Participants had migrated to the United States or Canada, leaving one or more children behind in their home country. Parents were recruited via word of mouth and publicly accessible Caribbean community groups on social media. Semistructured interviews were video‐recorded, transcribed verbatim, and analyzed. Results We derived six themes: (a) reliance on family caregivers, (b) communication and connection, (c) commitment to education, (d) financial support and resource management, (e) emotional distress, and (f) joint parenting roles and family conflicts. Conclusion These findings highlight the emotional, financial, and family relationship stressors faced by Caribbean transnational mothers and fathers, as well as their resilience and adaptive strategies in long‐distance parenting. Implications The study underscores the need for support systems to strengthen parent–child relationships, improve financial transparency, and assist families in managing transnational caregiving dynamics. These insights are particularly valuable for family scholars and practitioners working with Caribbean families, informing strategies to better support transnational parenting dynamics.