The English modals have been used as case studies in many domains of linguistic enquiry. Their diachronic development and patterns of synchronic variation in historical and contemporary corpora have been used to develop theories of linguistic representation, to further understanding of correlations between structure and use, and to investigate relationships between form and meaning. However, much of this research explores only the modals themselves: relatively little attention has been given to the study of modal collocations. In this article, we explore variation and change in collocational patterns of two modals (may and might) when they appear directly adjacent to the adverb well. Our analysis is corpus based, using quantitative data to explore macro-level trends in recent American English, and qualitative analysis to explore micro-level variation, particularly with regard to the development of concessive uses of may and might, and post-modal meanings more generally. We foreground the idea that modals show subtly different diachronic trends in specific collocations compared to perceived trends when looked at as an isolated class of auxiliary verbs.