Why did Portuguese diplomacy survive in Benin and Warri while Christian conversion failed to produce lasting social transformation? What explains the survival of diplomatic exchange in the face of the fragility of missionary success? This paper explores the diplomatic and religious aspects of Portuguese relations with the kingdoms of Benin and Warri from the late fifteenth century to 1725. It argues that African political agency, rather than European initiative, was the decisive structural feature of early Afro-Portuguese relations in the Bight of Benin. Diplomacy endured because the Oba of Benin and the Olu of Warri found Portuguese engagement useful for trade, prestige, military advantage, and external legitimation. Christianity, however, failed to achieve lasting social transformation because it threatened the sacred foundations of kingship in Benin and, in Warri, remained largely a court religion rather than a socially translated and locally sustained faith. The divergence between diplomatic success and missionary failure was therefore not incidental: it reflected African rulers’ capacity to select, adapt, and refuse foreign influence according to local political priorities.