BACKGROUND AND OBJECTIVES: Smart home auto-prompting has the potential to increase the functional independence of persons with dementia (PWDs) and decrease caregiver burden as instrumental activities of daily living (IADLs) are completed at home. To improve prompting technologies, we sought to inductively understand how PWDs responded to auto-prompting while performing IADL tasks. RESEARCH DESIGN AND METHODS: Fifteen PWDs completed eight IADLs in a smart home testbed and received a hierarchy of verbal auto-prompts (indirect, direct, multimodal) as needed for task completion. Two researchers viewed archived videos and recorded the observed behaviors of the PWDs and their reflections watching the PWDs. Using qualitative descriptive methods, an interdisciplinary analytic team reviewed transcripts and organized data into themes using content analysis. RESULTS: Context and Communication emerged as the major themes, suggesting that positive user experiences will require auto-prompting systems to account for a multitude of contextual factors (individual and environmental) such as level of cognitive impairment, previous exposure to task, and familiarity of environment. Communicating with another human rather than an automated prompting system may be important if individuals begin to exhibit signs of stress while completing activities. DISCUSSION AND IMPLICATIONS: Additional work is needed to create auto-prompting systems that provide specific, personalized, and flexible prompts. Holistic conceptualization of "successful task completion" is needed and a positive end-user experience will be key to utility. Such systems will benefit from including positive reinforcement, training, and exploration of how, and whether, direct human involvement can be minimized during the provision of in-home care.