Upon conviction, individuals receive the stigmatizing label “criminal offender.” Existing stereotypes about criminal offenders may be integrated into the self-concept, a phenomenon known as self-stigma. In many stigmatized groups, self-stigma is a robust predictor of poor functioning (Livingston & Boyd, 2010; Schomerus et al., 2011). However, little is known about how self-stigma occurs (Corrigan et al., 2006), and there has been limited research with criminal offenders. This study examines a theoretical model of self-stigma in which perceived stigma leads to stereotype agreement, internalized stigma, and then to anticipated stigma. A sample of 203 male jail inmates completed assessments of these constructs just prior to release. Results show a significant indirect path from perceived stigma to stereotype agreement to internalized stigma, but not to anticipated stigma. However, perceived stigma was directly related to anticipated stigma. In conclusion, perceived stigma affects the self through two processes: it indirectly leads to internalized stigma through one avenue, and directly leads to anticipated stigma through a separate avenue. Race, criminal identity, and attitudes toward criminals were examined as moderators.