Work integration social enterprises (WISEs) in the United States represent a market based approach for workforce development and labor market integration that offer employment and training opportunities as well as bridges to the mainstream labor market. Historically developed to create separate spaces of work for populations considered less able to compete in mainstream labor markets, such as people with physical and developmental disabilities, as this article will show, WISEs have evolved to target other disadvantaged and marginalized communities such as individuals suffering from homelessness, youth disconnected from both school and labor markets, formerly incarcerated individuals seeking reentry into employment, and welfare recipients required to work for benefits or as benefits are timed out. This article traces the historic evolution of the WISE sector. The review highlights the ways in which the organizational model has been adapted in response to shifting social constructions about appropriate level of integration and employment norms for disadvantaged groups as well as the changing nature of jobs in the entry level labor market. Further, this paper illustrates that newer (non-disability related) WISE organizational models have different resource generation strategies compared to the older WISE models, may be more exposed to market forces in their social business niches, and must contend with the increased vulnerabilities faced by workers in an era of welfare safety net erosion.