Research in the orientation of for-profit companies suggests a dichotomous choice between a transactional or relational orientation. Yet, nonprofit organizations (NPOs) are inherently different in their operations and approaches and deserve special consideration. Numerous NPOs seek to achieve social goals, such as poverty alleviation, by conducting interventions in communities with the aid of donations and volunteer labor. Building upon the Transformative Charity Experience concept and the triad model (i.e., NPOs, donors/volunteers and communities), the present research utilizes case study data from NPOs and qualitative data from an impoverished community in Central America to reveal that the transactional/relational orientation model is too simplistic to adequately capture poverty alleviation efforts, and a richer model of the interplay of community and NPO engagement is developed. Further, although NPOs and communities both exhibit a strong desire for greater engagement, numerous tensions exist that pull NPOs away from higher to lower levels of engagement.