Conversational entrainment, a pervasive communication phenomenon in which dialogue partners adapt their behaviors to align more closely with one another, is considered essential for successful spoken interaction. While well-established in other disciplines, this phenomenon has received limited attention in the field of speech pathology and the study of communication breakdowns in clinical populations. The current study examined acoustic-prosodic entrainment, as well as a measure of communicative success, in three distinctly different dialogue groups: (i) healthy native vs. healthy native speakers (Control), (ii) healthy native vs. foreign-accented speakers (Accented), and (iii) healthy native vs. dysarthric speakers (Disordered). Dialogue group comparisons revealed significant differences in how the groups entrain on particular acoustic–prosodic features, including pitch, intensity, and jitter. Most notably, the Disordered dialogues were characterized by significantly less acoustic-prosodic entrainment than the Control dialogues. Further, a positive relationship between entrainment indices and communicative success was identified. These results suggest that the study of conversational entrainment in speech pathology will have essential implications for both scientific theory and clinical application in this domain.