This study evaluated how students enrolled in a comprehensive post-secondary transition program learned how to use text-to-speech (TTS) software to read higher-level written text. Using a pre- and post-test research design, researchers examined whether direct instruction effectively taught students to use a TTS program. We used third and sixth-grade easyCBM passages and corresponding reading comprehension measures to evaluate students' use of the TTS software and determine if TTS increased reading comprehension. Findings suggest that the use of direct instruction can facilitate the use of assistive technology and TTS readers. Implications for further research, practice, and policy are discussed.