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The School-to-Prison Pipeline (STPP) is a barrier for many students identified with disabilities, particularly those who are also from other historically marginalized groups. While special education transition research examines postschool outcomes in further education, employment, and community engagement, there is a gap between it and the research on the STPP phenomenon. This gap is partly attributable to a narrow paradigmatic focus in special education scholarship. A critical content analysis, coupled with a secondary analysis of a large-scale, longitudinal dataset, provides a two-pronged approach to understanding this gap and to illustrate a more complex relationship between the STPP and poor transition outcomes. Frameworks for expanding research for the purpose of dismantling the STPP and improving transition opportunities and outcomes are identified.