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Postsecondary students with disabilities face significant challenges accessing and realizing the opportunities offered by a college degree, yet postsecondary institutions often fail to collect and track data that can help. Utilizing the Loss/Momentum Framework, we surveyed 162 postsecondary students with disabilities from 27 institutions about supports and challenges during their first year. Over eight months, we observed curvilinear trends reflecting increasing self-rating of academic success and building relationships, and decreasing ratings of work-life balance, financial stability, mental health, and stress management. We also observed significant differences between the fall and spring semesters. Results can help postsecondary institutions about points of loss and momentum for students with disabilities on their path to a college degree.