Indigenous communities worldwide navigate complex intersections of cultural preservation, urbanization, and access to culturally responsive social support. This paper offers a comparative analysis of two geographically and culturally distinct Indigenous contexts: the Edo people of Benin Kingdom in Benin City, Nigeria, and Indigenous communities in Peterborough, Ontario, Canada. The analysis examines how cultural identity systems, urbanization pressures, land rights, and social work practice intersect to shape Indigenous wellbeing. The comparison reveals both convergent challenges, including colonial disruption, urban migration, and institutional marginalization, and divergent pathways for cultural continuity, custodianship, and community-led support. Findings underscore the necessity of decolonizing social work practice, centering Indigenous leadership, and embedding cultural safety frameworks to support Indigenous resurgence. The paper concludes with implications for Doctor of Social Work (DSW) practice, emphasizing that culturally responsive support must address structural dispossession, honor Indigenous epistemologies, and privilege community-determined pathways to healing and inclusion.