Background: Little is known about how health issues identified at the annual health check (AHC) are followed up and addressed, how participants self-manage their health in between AHCs, and what support they receive. This research aimed to explore this. Methods: People with intellectual disabilities (n = 12), and/or their supporters residing in Wales, were interviewed following their AHC and again at 6 and 11 months. A recurrent cross-sectional thematic analysis was undertaken. Results: Five main themes emerged from interview one: going for a health check, issues identified, and actions taken, supporting the self-management of health, the personal context, and addressing health inequities. Four main themes emerged from follow-up interviews: follow-up, supporting the self-management of health, the need for reasonably adjusted health services, and going for another health check. Conclusion: A broader system of support around the AHC is required if people are to achieve or maintain the best possible health.