Russell had two theories of names and one theory of description. Logically proper names are Millian names, which have only denotation but no connotation. Ordinary names are not genuine names but disguised definite descriptions subject to quantificational analyses. Only by asserting that ordinary names are definite descriptions could Russell motivate his theory of description to solve three problems for Millian names, namely, Frege's puzzle, empty reference and negative existentials. Critics usually discuss Russell's theories of names and his theory of description separately. This paper takes a new perspective and presents a dilemma for the overall project, arguing that it is hard to be a Russellian about names coherently. The central issue is whether contextualisation is semantic or pragmatic in nature, an issue very much alive in contemporary debates. This paper traces Russell's ambiguity on this matter back to his conception of the roles of knowledge by acquaintance and knowledge by description in naming.