Students with attention-deficit/hyperactivity disorder (ADHD) and/or learning disabilities (LD) experience significant challenges in making the transition from high school to college. This study examined the ways first-year college students with ADHD, LD, ADHD+LD, and comparison peers differ in engagement, core self-evaluation, high school preparation behaviors, and goals/expectations. Participants were from the 2010 Cooperative Institutional Research Program Freshman Survey, including students with ADHD (n = 5,511), LD (n = 2,626), ADHD+LD (n = 1,399), or neither disability (n = 5,737). Controlling for SAT/ACT scores, family income, and parent education, students with ADHD, LD, or ADHD+LD differed from peers on self-ratings of academic and creative abilities and psychosocial functioning; school disengagement, substance use, and emotional difficulties during their last year of high school; reasons for attending college; and expectations for college activities. Several differences were found between disability groups. Implications for college support services and future research are discussed.