On Dec. 21, 2020, Congress lifted the 26-year ban on federal student aid--specifically, the Pell grant--for those who are incarcerated. The decision came after a long push for prison reforms that included calls for a greater emphasis on rehabilitation, reducing prison populations, and making prison sentences less harsh. New England has long been a decisive voice in providing postsecondary education behind bars, and the region persevered even after Pell grants were denied to inmates following the 1994 "Tough on Crime" laws. This brief explores the statistics and demographic information of incarcerated people in New England and in the U.S. It examines the impact of higher education on recidivism, employment outcomes, and self-concept of people in the region. The analysis also integrates qualitative data in the form of first-hand perspectives obtained in interviews with professors, Department of Corrections coordinators, and inmates themselves. The brief concludes by sharing promising practices that exist in the region can serve as models for creating postsecondary education programs in New England prisons.