The purpose of this qualitative multiple case study is to describe how culture, disability, and prospective first-generation college student status influenced the transition decisions of five native Hawaiian students with specific learning disabilities who attended a Hawaiian-focused charter school. Students had strong ties to their history and culture which influenced all facets of their lives including their decisions about the future. Accessing postsecondary education (PSE) was viewed as a means to employment that would enable them to support their family members. The lack of economic, social, and cultural capital may present a larger barrier to accessing PSE than disability. Implications for personnel who are tasked with developing and maintaining culturally appropriate curricula and programs for students are discussed.