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Evaluation in complex programs assembling multiple actors and combining various interventions faces contradictory requirements. In this article, we take a management perspective to show how to recognize and accommodate these contradictory elements as paradoxes. Through reflective practice we identify five paradoxes, each consisting of two contradicting logics: the paradox of purpose—between accountability and learning; the paradox of position—between autonomy and involvement; the paradox of permeability—between openness and closedness; the paradox of method—between rigor and flexibility; and the paradox of acceptance—between credibility and feasibility. We infer the paradoxes from our work in monitoring and evaluation and action research embedded in 2SCALE, a program working on inclusive agribusiness and food security in a complex environment. The intractable nature of paradoxes means they cannot be permanently resolved. Making productive use of paradoxes most likely raises new contradictions, which merit a continuous acknowledging and accommodating for well-functioning monitoring and evaluation systems.