This paper presents a qualitative, multisite comparative case study from two midwestern high schools investigating high school stakeholder perceptions of grading practices experienced while transitioning from a system that primarily utilized historical grading practices to a more contemporary, reformed system implementing an iteration of Standards-based grading. The review of literature provides a synthesis of the current state of grading practices and reform efforts that intersect with historical, traditional practices as well as literature related to stakeholder perceptions. Three primary themes emerged from the findings across both sites as it related to perceptions of implementation and transition of grading practices: comfort, academic relevance, and fidelity of implementation. The findings and analyses primarily focus on a student perception perspective of school interest and the school experience as well as student perception whether the grading reform transition still held on to previous, legacy grading practices. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]