As a pilot site selected to participate in Illinois' Shifting Gears (SG) initiative in 2007, Oakton Community College (OCC) partnered with Presbyterian Homes to develop a bridge course to prepare a cadre of their employed Certified Nursing Assistants (CNAs) to enter college-credit prerequisite courses to a Practical Nursing program. Oakton Community College, located in Skokie, Illinois, is a comprehensive community college serving 450,000 residents in suburban Chicago. Presbyterian Homes is a large, continuing care retirement community with over 1,600 residents among five campuses in Chicago and nearby suburban areas. The intended outcome of the contextualized bridge curriculum was to provide a short-term, engaging, accessible, developmental education experience to a select group of CNAs to prepare them for credit-level instruction. Shifting Gears is a workforce development initiative sponsored by the Joyce Foundation and in Illinois, also supported by the Illinois Department of Commerce and Economic Opportunity (DCEO). In the first phase of SG, ten community colleges received grants to develop bridge courses to provide low-skilled or low-income adults with the training necessary to prepare them for high-demand, middle-skill jobs that provide family supporting wages. Three high-demand occupational clusters were targeted in the SG initiative: transportation-distribution-logistics, manufacturing, and health care. This paper provides a practice description of the bridge program, describes the challenges faced by the partner institutions and the strategies they used to overcome them, and discusses the outcomes of the initiative.