This study explores the grading disparities among ninth-grade students within the American educational system, emphasizing the comparative analysis between economically disadvantaged students (indicated by Free or Reduced-Price Lunch status) and their more advantaged counterparts across urban, suburban, and rural locales. Drawing on a robust dataset of 65,017 first-time, full-time ninth graders from Arkansas, spanning the academic years 2020-21 to 2021-22, this research employs logistic regression analysis to uncover the nuanced relationships of socioeconomic status and geographical setting on course failure rates. The ninth grade is highlighted as a critical juncture in the U.S. educational trajectory, serving as a foundational year that significantly influences students' future academic and career pathways. My findings reveal that, although rural students initially present with lower failure rates, a detailed logit analysis accounting for individual and district-level characteristics demonstrates that rural ninth graders face the highest risk of course failure, especially among those with Free or Reduced Lunch (FRL) status. These results underscore the pressing need for implementing equitable grading practices and bolstering professional development for educators in rural areas to mitigate these disparities. This study contributes to the broader field of educational equity by highlighting systemic challenges and advocating for targeted interventions to support disadvantaged students, particularly in the pivotal year of ninth grade.