People with concealable stigmatized identities, such as a criminal record, often anticipate stigma from others. Anticipated stigma is thought to cause withdrawal from situations in which there is the potential for discrimination, which then negatively impacts behavior and functioning. This may have implications for offenders reentering the community, possibly hindering community integration and encouraging maladaptive behavior postrelease. Drawing upon a sample of 197 male jail inmates, we examine a theoretical model in which anticipated stigma during incarceration predicts behavioral outcomes 1 year after release from jail (i.e., recidivism, substance use disorder symptoms, mental health symptoms, community adjustment) through social withdrawal. Anticipated stigma during incarceration predicted social withdrawal three months postrelease, which then predicted more mental health problems 1 year postrelease. Stigma resistance and optimism buffered the effect of anticipated stigma on social withdrawal. Race moderated multiple paths in the model, suggesting that the relations between anticipated stigma, social withdrawal, and adjustment are more pronounced for White offenders.