Students who successfully complete grade nine are substantially more likely to graduate from high school than are students who fail the freshman year. However, many middle grades students are not academically prepared for ninth grade. This report addresses five questions that can help school leaders ensure that middle grades students know the courses they need to take before ninth grade: (1) Are students enrolled in the right courses that will enable them to achieve their postsecondary goals?; (2) Do ninth-grade students feel prepared to succeed in rigorous high school studies and are they engaged in completing challenging assignments?; (3) Do ninth-grade students possess the literacy and numeracy skills needed to succeed in challenging high school studies?; (4) Do ninth-grade students possess the independent learning skills required for success?; and (5) Are students getting the extra help they need to pass challenging courses and the guidance they need to set and achieve postsecondary goals? (Contains 3 footnotes, 1 figure and 15 tables.)