Organizational difficulties are major obstacles for many students with learning and behavior problems. These students often neglect to separate notebooks into various subject areas, forget to bring necessary items to class, and stuff assignments randomly into their book bags and pockets. Students' disorganization, including their inability to keep track of assignments and turn them in on time, can contribute to low grades and academic failure, particularly beginning in secondary school when teacher expectations are greater and supervision of students tends to be more limited than during the elementary years. Students with learning challenges may not acquire essential skills unless they are provided with systematic direct instruction; youth who fail to apply organizational skills may not have had the opportunity to acquire them through an explicit instructional approach. This oversight places struggling students at increased risk for unsatisfactory or failing grades and tends to heighten misperceptions of their academic performance in relation to that of their more successful peers. Can organizational skills instruction (OSI) help middle school students at risk behaviorally and academically? In this study, students who received training in self-monitoring of assignments were able to accurately monitor their academic performance and improved their grades in academic classes. (Contains 3 figures and 1 table.)