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This paper examines the presence of prior criminal history questions in undergraduate admissions among a unique set of postsecondary institutions: those that use the Common App and that sponsor higher education in prison programs. A sub-analysis examines these select institutions in the context of the U.S. Department of Education’s 2016 Second Chance Pell Pilot Program, an Experimental Sites Initiative that temporarily lifts the ban on Pell grant eligibility for incarcerated people. Using critical descriptive analysis and a framework of educational equity, we document changes in inclusion of prior criminal history questions among this set of institutions between 2018 and 2019, after the Common App removed required questions about criminal history from its standard platform in August 2019.