Purpose: This study examines the objectives, nature, and perceived outcomes of school-nongovernmental organization (school-NGO) engagements in the Israeli education system, focusing on a single case study of a school-NGO interaction. We aim to characterize the conflicting motivations of each stakeholder involved in the creation and formulation of such engagement and to capture the process of interaction--from its initiation through the decision to continue, expand, or abolish these relations. Research Design: We employ a case study approach based on in-depth interviews with school principals, the NGO's CEO, representatives of the local education authority and Ministry of Education, and the Israeli parliament's Education Committee director, in addition to publication analysis, to provide a comprehensive view of the interaction from the stakeholders' perspectives. Findings: We find that school-NGO interaction results from multidimensional relations, wherein each involved entity holds a set of aims and motivations that intermingle with those of other entities to create and form the engagement. School-NGO interaction can be considered a form of entrepreneurship within the education system, with each stakeholder acting entrepreneurially to gain value, attain resources, and mitigate risks in a proactive and innovative matter. All stakeholders employ this initiative to address their own, sometimes conflicting, goals and to benefit according to their own agendas. Conclusions: We conclude by discussing possible theoretical and practical implications involving school principals' agency and NGO-school engagements in the local and global context.