College and career readiness programs are critical for vulnerable student populations, including low-income, economically disadvantaged students, and students of color, because these students have been historically and consistently identified as not college and career ready. Many factors contribute to the culmination of readiness that goes beyond academic skill and ability. Under-served student populations face increased barriers to readiness that influence their engagement with college and career programs, and their overall degree of preparedness for postsecondary transition. This qualitative study captured the perspective of five counselors in Duval County Public Title 1 high schools to understand the level of access students have to college and career readiness programs, student holistic preparedness, and the barriers students face in postsecondary transition. This study adds to the literature by offering a viewpoint of day-to-day realities from educators tasked with preparing students for college and careers. The findings from this study resulted in seven themes: (a) students have more access to college and career counseling than programs; (b) fewer students are prepared for college; more are prepared for a career; (c) academic rigor, cognitive, and non-cognitive ability impact overall preparedness; (d) barriers to college enrollment play a leading role in students’ perception of preparedness; (e) parent engagement and involvement are pivotal in postsecondary transition planning; (f) district awareness of program outcomes and resource needs is a necessity, and (g) college and career readiness programs ought to start earlier. This study has significant implications for public school districts, including school administrators; higher education partners; parents; and city and community stakeholders.