This project develops and evaluates HealthChecker, a web-based application. The design employs a cognitively accessible graphic user interface to lead an individual with cognitive disabilities through a daily self-assessment routine, querying the presence or absence of symptoms such as physical pain or discomfort. Simple self-care options are presented based on user input. HealthChecker is evaluated through self-assessment with authorized persons such as family members or caregivers through push notifications and web display; thereby letting them know when help is most needed and allocate their support as effectively as possible. Participants include a group of 20 individuals with significant cognitive disabilities in supported living situations to participate in focus groups, usability testing, and feasibility evaluation. Evaluation results are used to identify requirements for full development of a deployable system.