The interactive STANDUP software was developed to provide children who use augmentative and alternative communication (AAC) with a “language playground.” The software provides appropriate functionality for users with physical, speech, and language impairments to generate and tell novel punning riddles at different levels of complexity. STANDUP was evaluated with nine children with cerebral palsy during an eight-week study. Results show that the participants were able to generate and tell novel jokes with minimal or no support. The use of STANDUP impacted favorably on general AAC use. The study results also suggested that STANDUP could potentially have a positive effect on social and pragmatic skills. Further research to investigate the impact of STANDUP on communication skills is proposed. Suggestions for future software development include providing users with opportunities to complete jokes and to integrate online dictionaries when new vocabulary is encountered.