This study examined an intervention package incorporating an iPad-based augmentative and alternative communication (AAC) application, Proloquo2Go, to improve wh-question-answering skills in a 15-year-old adolescent with autism. A single-case, multiple baseline design across three types of wh-questions ("what," "where," and "who") was employed. The intervention included a least-to-most prompting hierarchy, interval reinforcement, cue cards, and question-related visuals. Results indicated a functional relationship between the intervention package and increased unprompted correct responses for each wh-question type. Additionally, the participant maintained these gains following a two-week break, and generalization probes revealed consistent performance across novel settings, different individuals, and varied question formats. These findings suggest that iPad-based AAC interventions, particularly those that combine structured prompting and reinforcement strategies, may effectively enhance and sustain communication skills in adolescents with autism.