This case report addresses the linguistic and motor speech development of a child born prematurely at 24 weeks’ gestation. Because of the complex nature of this child’s developmental trajectory he was evaluated and treated for suspected Childhood Apraxia of Speech, a disorder which is difficult to differentially diagnose. Now at age 4 years his clinical presentation is consistent with expressive and receptive language disorder with mild dysarthria. This work presents for consideration the inherent difficulty in diagnosing and treating children with rare and underreported conditions such as extremely preterm birth and very low birthweight. Additionally, this report explores how clinicians with distinct theoretical orientations (e.g., motor vs. linguistic) viewed this child from divergent perspectives, causing clinical disagreement. Consideration is invited of how we view communication disorders in complex developmental situations, informed by both historical perspectives and existing research on speech and language development in children born extremely preterm.