This study documents how organizational strategies underlying college counseling departments modify counselors’ ability to perform their academic and college advising duties. To examine this, fifteen semi-structured, in-depth interviews with public high school counselors in Southern California were conducted. A district’s commitment to college access and opportunity, as well as parents’ expectations for maintaining a college-going culture, shaped the nature of college counseling and organizational habitus in a school. Counselors reported that access to different forms of institutional support and resources diminish or exacerbate the structural constraints known to surface in public schools. This influenced when and how counselors advised students, which offered different views of the educational opportunity structure. Additionally, findings indicate that both college preparation programs and culturally sensitive counselors work to remedy educational disparities and increase the college enrollment rates of working-class minority students.