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Studies on CSO legitimacy highlight the undermining effect of incorporation in the aid system. It remains unclear, however, why donors continue to fund local CSOs lacking grassroots legitimacy. This article examines the case of an East African CSO that continues to attract donors despite being considered illegitimate by the grassroots. The research identifies six legitimacy sources: professionalism, agenda, strategy, track record, membership and governance. It finds that donors and grassroots interpret the first three sources (professionalism, agenda and strategy) in an opposing manner. Thus, the exact same characteristics that provide donor legitimacy simultaneously bring grassroots illegitimacy. The article subsequently identifies three mechanisms that explain why a lack of grassroots legitimacy is not a problem for donors: (1) donor priorities and capacities; (2) the CSO’s monopoly position; and (3) perception …