This article, published in the Journal of Education Placed at High Risk investigates the experience of 229 low-income students of color who participated in an innovative high school internship program between 2011 and 2015. Using mixed methods (interviews, observations, and survey), the authors aim to understand the types of knowledge, information, and supports these students develop and expand in relation to careers and the college-going process. The authors draw on students’ community cultural wealth to highlight the way the internship program supports students’ aspirational, navigational, linguistic, resistant, and social capital.