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A great deal of research has been done examining the revolving door between homelessness and incarceration. This study contributes to that literature by examining the differences between homeless people with and without felony convictions. Using data collected during the 2014 Point in Time Count conducted in three counties in Central Florida, this study examines differences in length of time homeless, substance abuse, and health outcomes among a sample of nearly 600 people. Specifically, I examine if the amount of time since the most recent felony conviction has a more serious negative impact on someone’s lives compared to a felony conviction that is years or even decades old. This analysis is important in better understanding the role a felony conviction can play in the lives of homeless people.