Engaging employers with youth in workforce preparation activities is widely supported by program providers as a good practice. Research, although limited, supports this practice as well. This paper describes the findings from 58 interviews with youth program providers, employers, and policy-makers that explored the inclusion of employers in workforce preparation activities for disadvantaged youth. We examined the degree to which youth and employers are prepared to engage with each other, how race and culture influence the entire experience, and whether program and policy efforts to increase employer engagement are in scale with youth program demand. The research highlighted important disconnects between program providers and employers and the affect these disconnects may have on expanding employer involvement. Implications for program development are also discussed.