A key issue in fostering transition to postsecondary education for students with disabilities is documentation verifying the nature of the disability and supporting the need for services and reasonable accommodations. Documentation guidelines assist postsecondary disability service providers in making decisions about eligibility and reasonable accommodations. However, documentation is often varied in scope, comprehensiveness, and quality, requiring a great deal of professional judgment during the review process. This study examined service provider decision-making when presented with documentation of learning disability with varying levels of information. Results indicated service providers’ value comprehensive Objective Evidence, but importance of the data used in decision-making varied by demographic variables, such as years of experience and type of training in reviewing disability documentation. Implications for practice are addressed.