In considering the Cambridge School of intellectual history, we should distinguish Skinner's conventionalism from Pocock's contextualism whilst recognising that both of them argue that the study of a text's linguistic context is at least necessary and perhaps sufficient to ensure understanding. This paper suggests that although "study the linguistic context of an utterance" is a valuable heuristic maxim, it is not a prerequisite of understanding that one does so. Hence, we might shift our attention from the role of linguistic contexts in understanding a text, to the role of ideational contexts in our explanations of meanings or beliefs. The explanatory role of contexts can be unpacked in terms of traditions and dilemmas. Here the paper also considers how this approach differs from that of the Cambridge School.