This study examines interactions between students with atypical motor and speech abilities, their teachers, and eye tracking devices under varying conditions typical of educational settings (e.g., interactional style, teacher familiarity). Twelve children (aged 4–12 years) participated in teacher-guided sessions with eye tracking software that are designed to develop augmentative and alternative communication (AAC) skills. Assessments of expressive communication skills before and after the testing period demonstrated significant improvements. 164 sessions conducted over a 3-month period were analyzed for positive engagement (e.g., gaze direction, session time) and system effectiveness (e.g., lag time, gaze registration) between integrated and non-integrated systems. Findings showed that integrated systems were associated with significantly longer sessions, more time spent looking at the screen, greater proportion of gaze targets registered by the system, and higher response rate to prompts from teachers. We discuss the implications for the facilitated use of eye tracking devices in special education classrooms.