This report, the first in the series for the St. Leonard’s Ministries’ evaluation, focuses on five case studies. St. Leonard’s Ministries operates two, transitional, residential programs with supportive services—St. Leonard’s House (SLH) provides housing for adult men exiting prison, and Grace House (GH) provides housing for adult women exiting prison. The goal was to learn about the life experiences of program participants before, during, and after the program.Illinois Criminal Justice Information Authority (ICJIA) researchers embarked on a multi-year, multi-component evaluation to identify program components that are effective in contributing to successful resident outcomes, learn about the programs’ residents and operations, and analyze resident outcomes. Collectively, the reports will educate criminal justice professionals and the public about the potential benefit of a structured, residential, reentry program for formerly incarcerated men and women.