This qualitative study aimed to explore the experiences of Black and Latiné recent high school graduates in a large urban school district specific to the messages and support they received regarding course selection and postsecondary planning by comparing the type of school the participant attended. This research study aimed to understand how recent high school graduates experienced messaging about postsecondary pursuits and opportunities. The research considered Racialized Organization Theory and how Critical Race Theory, Critical White Studies, and Social Capital Theory intersect at the school system level to better understand the disproportionality in graduation rates between school types in a large urban school district. Interview participants were selected using snowball sampling. Questions about how participants experienced course selection, college-going conversations, and career exploration. This study unveiled stark differences in the experiences of study participants who attended catchment schools versus those who attended magnet schools. Participants who attended catchment schools appeared to be surviving high school while participations who attended magnet schools described thriving. Socialization, school climate, student and teacher mindset, course options, finances, and postsecondary planning played a role in participant experiences. A final analysis of how participants responded to direct questioning about school counselors uncovered that in this study, school counselors had a minimal impact, with two out of 21 participants articulating that a school counselor was a key support person. Using inquiry as a stance, the researcher provided a framework for thinking about how large urban districts can work towards creating support, structure, and equity in academic advising for Black and Latiné students in both catchment and magnet schools alike, with an intentional focus on catchment schools that show lower graduation and college matriculation rates. The researcher closes with suggestions for future research that centers on the experiences of young Black and Latiné high school students in the hope of improving student outcomes for urban high school graduates.