Purpose - This investigation determined how students with Learning Disabilities (LD) navigate the difficult transition from grade 8 to grade 9 compared to their non-disabled peers. This longitudinal study assessed group and grade differences on three observable, measurable factors found to be important for school success in grades 7 through 10. Method - Participants included a group of students with LD (n = 29) and their non-disabled peers (n = 29). Academic performance, attendance, and problem behaviors were measured for each student in 7th through 10th grade. Students were identified as "at risk" of not meeting basic school success if they fell below an empirically derived cut-off risk criterion. Results - Students with LD exhibited significantly poorer academic performance, lower attendance rates, and were at greater risk of not meeting basic school success. Grade 7 and 8 academic performance and grade 8 attendance correctly differentiated 88.9% of those at risk and 93.5% of those not at risk of poor school success. While 2/3rds of students with no disability recovered from this risk, only a little more than 1/3rd of students with LD recovered. Grade 7, 8, and 9 academic performance and grade 8 attendance predicted 100% of students who recover and 100% of students who do not recover. Discussion - The findings heighten awareness of the challenges presented by the grade 9transition for students with LD. Identifying this challenge for this particular population is the first step towards implementing preventative measures to facilitate success during this critical transition. This work extends beyond the LD population by identifying predictors of students at risk for 9th grade and predictors of students who fail to recover from a poor high school transition, both of which can assist educational stakeholders to be proactive in supporting a successful transition for students pre-identified as at risk and reactive by providing supports for students who exhibited a poor transition and are unlikely to recover. [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.]