Background: Employment is an important social determinant of health, and supporting individuals’ return to the workforce is likely to have robust impacts on their health and well-being. The aim of this study was to identify (a) the self-perceived employment needs and expectations of users of community employment services; (b) the assets, needs, and barriers to reemployment among users of community employment services; and (c) areas of priority for programmatic development, including implications for patient–worker needs assessment and care coordination in clinical settings.Methods: We conducted structured interviews with 71 adults recruited from three workforce development programs located in the Chicago metropolitan area serving vulnerable workers. Topics of discussion included job histories, financial and social assets, and the respondents’ motivation and expectations for their return to the workforce. We used descriptive statistics to analyze quantitative responses and performed content analysis for qualitative data.Findings: Users reported discrimination, legal barriers, family responsibilities, physical or mental health concerns, and needs related to transportation and housing as common challenges to reemployment. Concerns regarding navigating complex social support programs to meet individual and family needs, as well as uncertainty regarding what would qualify as sufficient employment in order to not be reliant on these programs in the future, were expressed.Conclusion/Application to practice: Health care providers have opportunities to identify those that may benefit from comprehensive referrals to reemployment programs and social services. Occupational health providers are also in a unique position to enhance workforce development programs through collaborations to better educate and support workers.