Adolescents with learning disabilities disproportionately come from lower socioeconomic status backgrounds, show normative deficits in academic skills, and attend 2-year, public colleges instead of 4-year institutions. However, students with learning disabilities are well represented at the United States’ most expensive and selective postsecondary institutions. We examined the psychoeducational functioning of students receiving accommodations for learning disabilities at a private, selective, liberal arts college. We also determined whether students had objective evidence supporting their disability diagnoses and academic accommodations. Most students showed above-average cognitive abilities, average academic skills, and no evidence of impairment. Although nearly all students reported academic problems, most lacked objective evidence of academic difficulties prior to college as well as relative or normative deficits in broad academic skills or fluency. Results indicate a need for greater reliance on objective, multimethod/multi-informant data in the diagnostic process. Results also highlight limitations in the current professional guidelines for documentation decision making in higher education.