Although calls to expand integrated employment opportunities have permeated recent legislative and policy initiatives in the United States, substantial numbers of adults with severe disabilities still work in segregated settings. We examined findings from events held in eight communities to solicit the views of parents and other family members (n = 93) on the state's shift from sheltered to integrated employment. Our interest was in understanding what maintained their attraction to segregated work settings and which factors would lead them to consider community employment as an appealing alternative. The considerations raised by participants were wide-ranging and highly individualized. However, factors related to ensuring safety, the availability of personal supports, and opportunities for relationship development were pronounced across these geographically and economically diverse communities. We offer implications for research and policy aimed at changing the employment landscape for individuals with severe disabilities.