This study examined how traditional-aged, first-year college students with specific learning disabilities adjusted to academic expectations as they moved from high school to a less monitored collegiate environment. Results of the study indicated that these students had difficulty moving beyond their established high school patterns by unrealistically expecting the same types and levels of services to be available in the postsecondary setting. The analysis suggested that these students struggled to develop the intellectual skills, practice emotional discipline, and move toward more independent behavior expected in the college environment. The purpose of the study was to examine systemic issues related to students with learning disabilities in their transition from the secondary to the postsecondary environment.