Entrepreneurship is often heralded as a pathway to poverty alleviation and community empowerment. However, the relational complexities between organizational actors and beneficiaries remain underexplored. This study examines the intertwined paradoxical tensions experienced by frontline workers (FLWs) and beneficiaries within microfinance organizations in Nepal, investigating how these tensions influence entrepreneurship in impoverished communities. Drawing on qualitative data, the study reveals three critical insights: (a) standardized organizational practices expand roles and entangle paradoxical tensions between FLWs and beneficiaries; (b) beneficiaries mirror FLWs’ relational approaches—ranging from affective to transactional approaches— to navigate tensions; and (c) the mirroring of relational approaches shapes beneficiaries’ (dis)engagement with entrepreneurial activities. These findings illuminate intertwined paradoxical tensions and their ripple effects on fostering entrepreneurship in impoverished communities. By integrating these insights, this study provides a novel relational framework for understanding how organizations shape entrepreneurship in impoverished communities.