The purpose of this article is to explore what college planning practices or demographic characteristics are associated with confidence in degree completion for college students with disabilities. A survey was used to gather retrospective data from undergraduate students with disabilities registered with a disability services office at a large doctoral-granting public four-year university (n = 260). A series of t-tests were conducted to test for significant differences in students' confidence of graduation by demographic factors and practices while in high school. Certainty in graduation was measured by students' self-reported likelihood of graduation on a five-point Likert-type scale. Results demonstrate that students at that university, who predict a high likelihood of graduation, report certain individual characteristics, attitudes, practices and activities as important to their eventual degree attainment compared to students not in those groups. These include talking with a college representative while in high school, registering with the disability service office during the first year of college, receiving special education services in high school and students who are deaf or hard of hearing self-report a higher likelihood of graduation. Students who were beneficiaries of the free and reduced lunch program in high school had a lower self-prediction of college graduation than non-free and reduced lunch program students.