The COACH is a prototype automated prompting system designed to encourage independent participation in daily tasks by older adults with dementia. Supervised, clinical trials with the COACH were promising, yet little was known about the capabilities of the system in an unsupervised, real-world environment or the needs of the system's users in such a deployment. To continue development of the COACH toward an unsupervised, real-world in-home deployment I employed an informed approach. First, the needs of the users of the system were identified through a national questionnaire completed by family caregivers of older adults with dementia and validated using a follow-up focus group. Participants indicated that the COACH should provide unobtrusive support of private or personal tasks by leveraging the remaining abilities of the older adults with dementia using the system, promoting independent task completion. Next, the performance of the COACH was evaluated in an unsupervised, real-world clinical deployment. One of the COACH modules responsible for tracking the interactions between the system users and objects in the environment was implicated as the cause of the majority of the failures, successfully identifying only 46.9% of the task steps completed by the trial participants. The technical factors limiting system performance in the real-world clinical deployment were synthesized with the needs of the users to develop technical design criteria which were used to guide the development of an improved COACH prototype. The performance of the new COACH prototype was evaluated in a second supervised deployment, resulting in the successful identification of 93.7% of the task steps completed by trial participants. Encouraged by these results, the COACH system is again ready for evaluation in an unsupervised, real-world environment.