The purpose of this grounded theory research was to determine what differentiates people with disabilities who leave Social Security Disability Insurance (SSDI) benefits due to increased income from those who cannot. Fifteen individuals, former and current participants in a Medicaid Buy-In program, were interviewed. Within the context of health and disability, four theoretical propositions were identified: education, opportunity to work, interpersonal support, and secure housing. Higher benefit levels were also found to be an effective barrier for many.