OBJECTIVES: Cognitive and behavioral impairments of children born extremely preterm (EP) (<28 weeks' gestation) and extremely low birth weight (ELBW) (<1000 g) may change with age. We assessed the individual stability of behavioral executive function (EF) from 8 to 18 years of age in children born EP or ELBW and their academic outcomes. METHODS: Participants comprised 180 children born EP or ELBW from a large geographic cohort. We investigated the frequency of 4 developmental groups (persistent, remitting, late-onset, and typical development) on the basis of dichotomized scores (typical versus elevated) at ages 8 and 18 years in 2 indices (the Behavioral Regulation Index [BRI] and the Metacognition Index [MCI]) of the parental form of the Behavior Rating Inventory of Executive Function. Adolescent academic outcomes were measured by using the word reading, spelling, and math computation subtests of the Wide Range Achievement Test, Fourth Edition. RESULTS: Most participants had a typical EF (BRI 61%, MCI 53%), followed by persistent (BRI 15%, MCI 16%), late-onset (BRI 12%, MCI 19%), or remitting (BRI 12%, MCI 13%) executive difficulties. Groups with executive impairments at age 18 years (persistent and late onset) had poorer academic outcomes than the typical and remitting groups. Shifting impairment categories between 8 and 18 years old was relevant to later academic outcomes. CONCLUSIONS: Most children showed stable and age-appropriate EF, although persistent and transient difficulties were observed and related to uneven academic outcomes. Studying the origins and consequences of the developmental stability of EF may contribute to the development of interventions to decrease the adverse neurodevelopmental outcomes of preterm birth.