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Developments in configurationality in relation to changing patterns in morphology and syntax are investigated to establish to what extent such developments support the traditional typological synthetic–analytic opposition and what evidence there is for assuming an independent configurationality parameter. Following an introduction to traditional analyses of configurationality from a typological perspective with a detailed review of the key formal criteria standardly employed in assessing differences between configurational and non‐configurational languages, there follows a discussion of key diachronic issues raised by developments in configurationality and their interplay with changing patterns in morphology and syntax. This includes an examination of the Latin–Romance transition and claims about the rise of configurationality through a critical comparison of changing patterns in syntheticity–analyticity, the emergence of functional categories, the rigidification of word order, and an assessment of the diachronic correlation between the weakening and possible loss of inflectional morphology and the concomitant rise of full configurationality. The results are, in turn, integrated with a discussion of configurationality in relation to the typological distinction between dependent‐ and head‐marking, critically reviewing the role of rich morphological marking for case and agreement in licensing non‐configurationality across a broad range of typologically diverse languages. The discussion concludes with a case study from the Latin–Romance transition in favor of a syntactic deconstruction of configurationality, demonstrating that perceived changes in surface configurationality can ultimately be derived from a gradual reversal in the head directionality parameter and the concomitant effects this has on the availability of discourse‐related edge‐fronting. This is a significant result as it offers an explanation of significant diachronic changes in, for example, the transition between Latin and Romance in terms of a single macroparametric change, doing away with the need for a somewhat dubious independent configurationality macroparameter, the relevant effects of which now fall out for free as part of the head parameter.