Given the increasing importance of education to socioeconomic attainment and other life course trajectories, early academic struggles can have long-term consequences if not addressed. Analysis of a nationally representative sample with official school transcripts and extensive data on adolescent functioning identified a social psychological pathway in this linkage between external feedback about early struggles and truncated educational trajectories. For girls, class failures absent of diagnosed learning disabilities engendered increasingly negative self-perceptions that, in turn, disrupted math and science course-taking, especially in family and peer contexts in which academic success was prioritized. For boys, diagnosed learning disabilities, regardless of class performance, engendered the same changes in self-perception and the same consequences of these changes for course-taking across family and peer contexts. These results reveal how ability labels and ability-related performance indicators come together to influence the long-term educational prospects of girls and boys attending mainstream schools in which the majority of students do not have learning disabilities or severe academic problems. Keywords: education, learning disability, academic failure, peers, and stigma.