The contextualist approach to utterance interpretation posits processes of “free” pragmatic enrichment that supply unarticulated constituents of the explicit content of utterances. While this proposal is faithful to our intuitions about the truth conditions of utterances, and accommodates the optionality of these pragmatic effects, there remains a doubt about whether contextualism can account in any principled way for what pragmatically derived material enters into explicit content, and what does not. This gap in the theory leads to objections that the putative process of pragmatic enrichment would massively overgenerate interpretations of utterances, having no way to exclude from explicit content elements of meaning that are truth-conditionally irrelevant. Here I discuss how a derivational account can sort explicit content from implicatures, where the former is a result of “developing” the linguistically-encoded form, while implicatures are entirely inferred, from fully propositional premises. Using the idea that enrichment is constrained to the minimum necessary to inferentially warrant the implications of the utterance, I show how the derivational account can address existing examples of alleged overgeneration, and that these rest on a failure to properly appreciate that the occurrence of such “free” pragmatic processes depends on the details of the particular context in which the utterance was tokened. I conclude with a discussion of what kind of systematicity should be expected from an account of processes whose outcome is inevitably context-specific.