Recently, apprenticeships have re-emerged as an effective means of preparing young people for the 21st-century workplace (Browning & Nickoli, 2017; OECD, 2018). Especially, community colleges have been actively implementing modern apprenticeships within their degree programs by offering degree apprenticeships (DAs). The purpose of this qualitative case study is to explore the opportunities, challenges, and strategies of implementing this new degree model as perceived by stakeholders at a community college. Harper College, based in the greater Chicago area, was chosen as the research site due to its well-established DA programs in modern occupations. The findings suggest that DAs serve as an outstanding tool for Harper to fulfill its core mission as a career technical education provider, successfully enhancing both academic achievement and job readiness among students Due to the programs' popularity and high completion rate of 66 percent, they also serve as a new income stream for Harper. However, implementing DAs comes with challenges since a paradigm shift is required to bridge the world of education and business. Finally, overall strategies for designing and delivering DAs are summarized as reconfiguration and coordination: a community college needs to reconfigure their existing resources to fulfill the apprenticeship framework and coordinate with various stakeholders to design and deliver the new learn-and-earn degree pathway.