Mobile technology provides increasingly accessible and normative tools for communication that does not require intelligible oral expression. For adolescents with autism spectrum disorders (ASD) and complex communication needs, mobile technology presents opportunities for inclusive social experiences and additional modalities for communicating with communicative partners (e.g., making a request to a partner who may or may not be within close proximity). This study examines using video prompting to teach four adolescent males with ASD, intellectual disability, and limited verbal expression of how to emit pictures to communication partners using text messaging technology. Results indicate acquisition was achieved and maintained when presented under the same conditions for three of the four participants. Attentional concerns were observed in the intervention sessions and warrant future investigation.