Objectives: There is debate about the extent to which imprisonment deters reoffending. Further, while there is a large literature on the effects of imprisonment, methodologically sound and rigorous studies are the exception due to problematic sample characteristics and study designs. This paper assesses the effect of imprisonment on reoffending relative to a prison diversion program, Community Control, for over 79,000 felons sentenced to state prison and 65,000 offenders sentenced to Community Control between 1994 and 2002 in Florida. Methods: The effect of imprisonment on recidivism is examined within one-, two-, and three-year follow-up periods using Logistic Regression, Precision Matching, and Propensity Score Matching. Results: Findings indicate that imprisonment exerts a criminogenic effect and that this substantive conclusion holds across all three methods. Conclusions: The main contribution of this study is that various methods yield results that are at least in a similar direction and support overall conclusions of prior literature that imprisonment has a criminogenic effect on reoffending compared to non-incarcerative sanctions. Limitations and directions for future research are noted.