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This historical study examines the issues surrounding the admission of underprepared students at Vassar College and Cornell University from 1865 to 1890. In doing so, the article discusses institutional controversies regarding the admission and subsequent education of academically inadequate students. Further, the article identifies educational practices aimed at remedying these deficiencies. Finally, the research considers Vassar’s and Cornell’s efforts to develop working relationships with emerging secondary schools. These efforts were intended to improve both Vassar’s and Cornell’s admission requirements and academic standards.