A successful freshman year of high school lays the foundation for the path to college: ninth-grade grades are powerful indicators of high school graduation, college access, and college degree attainment. However, the transition from eighth to ninth grade is a time when students' academic performance often declines. This report explores how Chicago Public Schools (CPS) students' grades declined during the transition to high school in more detail, and it considers how both eighth- and ninth-grade grades have changed since the original report was written. It examines GPA declines in arts and PE/health grades in addition to grades in the core subject areas, and it breaks down these declines by race/ethnicity, gender, and eighth-grade achievement and looks at how these patterns vary across schools. It also explores the relationships between failures in ninth-grade core and non-core courses, credit accumulation, and high school graduation. The report concludes by providing implications for high schools of the patterns in course performance and their relationship to high school graduation. This report is organized into the following chapters: (1) Changes in Core GPA between the Eighth and Ninth Grades; (2) Non-Core GPA Declines across the Transition; (3) Course Failure and High School Graduation; and (4) Implications. [This report was produced with the The To&Through Project and additional support was provided by the Consortium Investor Council.]