The majority of reminder systems are inflexible; reminders are issued at static, prespecified times. To be effective, cognitive orthotics should reason about what reminders should be issued and when. This paper describes the personalized cognitive orthotic (PCO), a system that uses plan-based reasoning to attain flexibility. PCO relies on local search techniques to generate high-quality reminder plans based on knowledge of the user’s plans and her typical behavior. PCO is being developed in concert with other technologies aimed at improved plan management, including systems that update a user’s plans and track action execution. We describe the PCO as it is implemented in the Nursebot application: where it provides timely and relevant reminders to elderly people who have cognitive decline that necessitates assistance in managing their daily activities.