The number of students with learning disabilities (SLD) at postsecondary institutions has tripled over the past three decades and now constitutes about 11% of undergraduate students (Joyce & Rossen, 2006; U.S. Department of Education, 2013). Research has found that SLD who use accommodations at their postsecondary institution are more successful in university than those who do not (Denhart, 2008; Skinner, 1999). Yet, research suggests that SLD do not request accommodations at expected levels (Wagner, Newman, Cameto, Garza, & Levine, 2005). This study's purpose was to investigate differences in psychological attitudes and factors between SLD who disclose and who do not disclose. In addition, the study examined what factors SLDs consider when deciding if they will self-disclose their disability to university personnel. To achieve these goals, 31 undergraduate students with learning disabilities completed a mixed methods study comprised of quantitative scales (The Self-Determination Scale [SDS], the Attitudes Towards Requesting Accommodations Scale [ATRA], and the Revised Self-Disclosure Scale [RSDS]). Fifteen of these participants then were invited to complete a 30 minute semi-structured interview. Results indicate that the total scores on the ATRA, SDS, and the RSDS were significantly different between the groups of students who chose to disclose and those who did not. In addition, data from student interviews uncovered nine factors that students indicated influenced their decision to disclose and how deeply they disclosed.