In this study we investigated the lives and academic histories of eight students enrolled in an alternative-school program in a mid-sized Midwestern city. Through the triangulation of interviews, fieldnotes, local newspaper articles, artifacts such as student work and information provided in cumulative folders, and a battery of measures of cognitive performance in reading, we constructed a case history of each student and an ethnographic portrait of the middle-school program in which they were enrolled. We then compared and contrasted these case histories and the program portrait to cognitivist, socioculturalist, and macrostructuralist explanations of school failure. Our findings suggest that no single explanation comprehensively accounts for the range or complexity of each or of all eight students' life histories or current patterns of school behavior. Our observation of instances of engaging and disengaging instruction for the students in the alternative program also provided some insight into how to approach the development of curriculum and instruction for students who struggle in school for a wide variety of reasons. (Contains 1 figure and 4 tables.)