Upon exiting high school, some African American students with disabilities experience difficulty accessing disability support services and appropriate accommodations. Many of these difficulties in access can be traced to high school transition planning as the source. To understand the underlying transitional barriers and sources of support, case studies were developed to examine the experiences of African American students with disabilities as they secured accommodations from disability services. The following themes resulting from the data were evident within the student portraits: (a) students believed deficit-ideologies undermined attempts at self-determination; (b) students emphasized the importance of adequate information prior to transition; and (c) students often refused to access services due to competing cultural identities. The theoretical frameworks of social and cultural capital were used to explore the transitional experiences of postsecondary African American students with disabilities.