Abstract In Late Latin, dolus ‘deceit’ expanded its semantic scope and took on the meanings of dolor ‘pain, suffering, grief, anguish’. This article lays out the literary and epigraphic attestations for dolus ‘suffering’ in full and discusses the difficulties in determining whether a change in semantics has occurred. Using digital resources such as Perseus Digital Library and the linguistic corpus LatinISE as the basis for quantitative analysis, suggested routes by which dolus took on the meanings of dolor are evaluated. The article proposes that analogy played an important role and suggests several instances of four-part analogy based around s-stem nouns and adjectives formed from them by the suffix -oso-. It also considers the way in which the prescriptivist rhetoric of ancient authors still shape modern scholarship on Latin. Late Latin features are not evidence of decay or the result of speakers being ill-educated or incompetent, and should not be discussed as mistakes. The article also considers how social hegemonies influence semantics and the study whereof, and how the dominance of certain voices in Latin may skew our understanding of the meaning of words.