The American education system has consistently produced disparate outcomes for Black students in terms of graduation rates and college readiness. A deep exploration of this problem reveals that Black students are oftentimes placed in less rigorous courses with less qualified educators who lack the skills to manage student behavior and provide high-quality instruction. A possible solution to this problem is the elimination of tracking, an approach to sorting students by ability levels that more often sorts students by privilege and social status. However, the removal of tracks (i.e., detracking) is a controversial change as it disrupts both teachers’ and the community’s deep-rooted idea of “what school should look like.” Teachers, who are on the front lines of detracking, must feel supported and heard when this initiative is in its initial implementation phase. More importantly, they must have a shared commitment, along with school leaders, to the program’s success. This qualitative study, which was done through individual teacher interviews, a review of training materials, and a focus group compiled of those interviewed to discuss initial findings, explores teacher perceptions of how they were prepared, engaged, and supported by school and system leaders during a detracking initiative that took place in three different high schools in one school district. The findings of this study will help educational leaders understand the complexities of this initiative and the planning and support needed to make it sustainable. Such themes that were discovered include the need for a pre-established collaborative culture and regular time for teacher collaboration. Most importantly though, this study reveals a larger issue with today’s educational practices. In a society that is rapidly changing, detracking should be considered an important re-structuring of our traditional school practices that better aligns with equity and the needs of today’s learners, rather than just another initiative.