People with disabilities that affect their speech, often use speech-generating devices (SGD), commonly referred to as Augmentative and Alternative Communication (AAC) technology. This technology enables practical conversation; however, there has been a growing interest in extending AAC to support more expressive forms of conversation such as humor. In this paper, we study how to extend AAC technology to support a subset of humorous expression: delivering timely humorous comments -- witty remarks -- through AI-powered interfaces. We conducted seven qualitative interviews with AAC users and performed thematic analysis to gain in-depth insights about their experiences and challenges with AAC technology, and the role humor plays for them. We developed four simple AI-powered interfaces designed to support users in creating timely humorous comments during real-time conversations. Through a user study with five AAC users, we explored how to effectively support the delivery of well-timed humorous remarks. We conclude with a discussion of recommendations for interface design based on both studies.
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