As international development practitioners, we are often caught in the middle—on one hand struggling to address the challenges and barriers to working in complex contexts; on the other hand, striving to meet the ambitious goals and targets required by donors. This essay explores the tension between these often contradictory pulls by drawing on the author’s experience and perspective as an education practitioner in the Democratic Republic of Congo (DRC). It argues that donor, government, and practitioner failure to develop an approach that accommodates the challenges of working in countries like the DRC results in education projects that are unsustainable and ineffective. The essay concludes with suggested actions that practitioners can take to improve implementation in challenging policy and resource environments.