Considering both demographic and technological changes in society, the potential of technology to support older adults has recently attracted much attention. For physically frail individuals with cognitive impairment, user-friendly technologies may facilitate activities of daily living. The current study assessed the performance of older adults without cognitive impairment (n = 27) and with mild cognitive impairment (n = 26) using three types of technology. Relationships between performance in the technology-based tasks and cognitive abilities (e.g., visual-spatial abilities), personality characteristics (e.g., self-efficacy), and previous technology experience were examined using a mixed-methods approach including video analyses and psychological testing. Findings underscore that both cognitive abilities and personality-related characteristics contribute to individual differences in users' performance. Nuanced knowledge of older adults' specific difficulties, abilities, and resources may help improve the fit between user needs and technological requirements, with implications for technology developers and practitioners.