While there have been steady increases in postsecondary education attendance by students with learning disabilities (LD), limited research has examined secondary schooling factors that may affect and promote their postsecondary educational aspirations and enrollment. Drawing on a sample of 370 students with LD from the National Longitudinal Transition Study 2 (NLTS2), the current study examined associations of a comprehensive set of factors (family, individual, school, and secondary schooling experiences) to postsecondary educational aspirations, enrollment, and alignment between the two, focusing on the role of secondary schooling experiences. Binary or multinomial logistic regression results showed that secondary schooling factors explained a significantly large amount of the variance in those outcomes; grades and school perceptions were the most consistent and critical predictors beyond other background characteristics. The schooling variables of grades, grade retention, overall school perceptions, and college entrance exams, were significantly associated with enrollment status, particularly for colleges. These findings highlight the importance of schooling experiences and the need for additional research in promoting educational aspirations and successful secondary transition to postsecondary education among students with LD. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]