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The Affordable Healthcare Act has, among other changes, created greater incentives to reduce health disparities in low-income communities across the country, which heightened the importance and expectations of community health workers (CHWs) as part of the clinical care team. These heightened expectations have begun to transition what has historically been a paraprofessional role into one that involves more clearly defined competencies and development needs. In an effort to meet these needs in the city of Chicago, a CHW basic certificate program was developed and launched at Malcolm X college (one of the seven city Colleges of Chicago), in collaboration with several community partners. This article presents the experience of this program, the challenges faced in its implementation, and lessons from this experience that may be relevant to others involved in the professional preparation of CHWs.