This constructivist case study examined how low-income students characterized their experiences with career development opportunities provided by a comprehensive college transition program designed to support their success. Overall, participants described career programming as advantageous since they honed skills (e.g., resume writing, interviewing) and learned unspoken rules (e.g., business etiquette) that would help them secure employment. They also benefited from practicing their interviewing and networking skills within a supportive environment. Although career programming was characterized as beneficial, some participants found narrow definitions of professionalism to be uncomfortable and a focus on business/industry to be limiting since they were distanced from their identities and interests. Furthermore, the programming was not value-added for some participants given their prior work and college preparation experiences. Our findings highlight the tensions of providing large-scale career development programming for low-income students with a range of other salient identities, interests, and employment experiences.