This article attempts to shed light on the issue of a possible link between the loss of ‘rich’ subject-verb agreement and the loss of verb raising in embedded clauses in earlier stages of the Mainland Scandinavian languages. Different versions of this so-called ‘Rich Agreement Hypothesis’ are compared in light of new diachronic data from the history of Danish. Examples of word order variation with and without verb raising over sentential adverbials were collected from a corpus of twelve sets of texts written in the Early Modern Danish period (ca. 1500–1700). Empirical results indicate that distinctions in person agreement in the verbal inflectional paradigm disappeared nearly 250 years before a significant decline in the frequency of verb raising. In order to explain a possible trigger for this change, the article closely examines the impact of structurally ambiguous word order and syntactic – not morphological – clues during acquisition.