We consider the challenges, and the virtues or otherwise, of undertaking a systematic analysis of the personal diaries and letters of a European traveller in Africa in the late nineteenth century. Our case study is Englishman Frank Oates, and the context is his interactions with the Ndebele of southern Africa in the 1870s. This case study affords us the opportunity to consider the European/African encounter on the eve of formal imperial rule. We assess the potential to reconstruct this colonial encounter in a manner that gives due weight to African agency. We consider the implications for our analysis of race, contingency, and the provenance of the source base and the intentions behind its creation, as well as taking into account silences and omissions, and that which Oates recorded but did not incorporate into his understanding of the Ndebele nation and its king, Lobengula. We provide historical context to the encounter and delineate how we seek to assess specific components of this encounter.