Health self-advocacy is associated with positive health outcomes, though existing research indicates that older adults may be at a disadvantage when self-advocating within the health care and disability support systems. This study examined perceptions of older adults’ health self-advocacy behaviors and the context under which they self-advocate for their chronic conditions. The study involved in-depth interviews with 37 older adults with chronic illnesses and disabilities and 9 geriatric case managers in South and Central Florida. Data were systematically analyzed for themes. Thematic findings revealed that concerns over quality of life is the most common motivator for older adults to engage in health self-advocacy and that self-advocacy involves gathering information to prepare for decision-making and confronting providers about the information gathered. The findings suggest that providers may help facilitate self-determination by framing health communication within the context of quality of life.