Designing Conversational AI systems to support older adults requires more than usability and reliability, it also necessitates robustness in handling conversational breakdowns. In this study, we investigate how older adults navigate and repair such breakdowns while interacting with a voice-based AI system deployed in their homes for medication management. Through a 20-week in-home deployment with 7 older adult participant dyads, we analyzed 844 recoded interactions to identify conversational breakdowns and user-initiated repair strategies. Through findings gleaned from post-deployment interviews, we reflect on the nature of these breakdowns and older adults' experiences of mitigating them. We identify four types of conversational breakdowns and demonstrate how older adults draw on their situated knowledge and environment to make sense of and recover from these disruptions, highlighting the cognitive effort required in doing so. Our findings emphasize the collaborative nature of interactions in human-AI contexts, and point to the need for AI systems to better align with users' expectations for memory, their routines, and external resources in their environment. We conclude by discussing opportunities for AI systems to integrate contextual knowledge from older adults' sociotechnical environment and to facilitate more meaningful and user-centered interactions.
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