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Rural outmigration presents a significant challenge for communities in Trinidad and Tobago, often causing tension over whether youth should stay or leave. This qualitative case study examines the perspectives of rural educators, students, and community members on how outmigration affects youth aspirations. Guided by the question, “How do rural educators, students, and community members perceive the economic and social implications of youth migration from their community?" the study explores how personal, economic, and cultural factors influence migration choices. Findings reveal that although limited local opportunities motivate many to consider leaving, strong connections to home often encourage students to stay. Participants emphasized the importance of local development and flexible pathways that enable young people to succeed while remaining in their communities.