People with speech disabilities may use speech generating devices to facilitate their speech, aka Augmentative and Alternative Communication (AAC) technology. This technology enables practical conversation; however it remains challenging to deliver expressive and timely comments. In this paper, we study how AAC technology can facilitate such speech, through AI powered interfaces. We focus on the least predictable and most high-paced type: humorous comments. We conducted seven qualitative interviews with people with speech disabilities, and performed thematic analysis to gain in-depth insights in usage and challenges of AAC technology, and the role humor plays for them. We designed four simple AI powered interfaces to create humorous comments. In a user study with five participants with speech disabilities, these interfaces allowed us to study how to best support making well-timed humorous comments. We conclude with a discussion of recommendations for interface design based on both studies.
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