Decisions about transitioning from work to retirement centered life are common among most older adults. These choices are often limited for persons with developmental disabilities (DD). Through focus groups and in-depth interviews with service providers, family members, and a potential retiree, this study identifies three themes pertinent to retirement choices of people with DD: (a) lack of retirement culture; (b) apprehensions about retirement; and (c) structural barriers to retirement. These results are useful to begin to ground retirement supports for persons with DD in an ecological perspective, and for exploring a multitude of issues and barriers that affect retirement choices.