Objective: An important distinction in models of housing for the homeless is whether programs that require abstinence prior to program admission produce better outcomes than unrestricted programs. Data from a large transitional housing program were used to compare client characteristics of and outcomes from programs requiring abstinence at admission and programs not requiring abstinence. Methods: The U.S. Department of Veterans Affairs (VA) Northeast Program Evaluation Center provided records of individuals who were admitted into, and discharged from, the VA Grant and Per Diem program in 2003–2005. Records contained information from intake interviews, program discharge information, and descriptions of provider characteristics. Analyses were based on 3,188 veteran records, 1,250 from programs requiring sobriety at admission and 1,938 from programs without a sobriety requirement. Group differences were examined with t tests and chi square analyses; predictors of program outcome were determined with logistic regression. Results: Individuals using drugs or alcohol at program admission had more problematic histories, as indicated by several general health and mental health variables, and shorter program stays. There were significant differences between groups in the frequency of program completion, recidivism for homelessness, and employment on program discharge, but effect sizes for these analyses were uniformly small and of questionable importance. Regression analyses did not find meaningful support for the importance of sobriety on program entry on any of the outcome measures. Conclusions: The results add evidence to the small body of literature supporting the position that sobriety on program entry is not a critical variable in determining outcomes for individuals in transitional housing programs.