Recidivism research on Hong Kong’s incarcerated population is limited, and little is known about the reoffending risk of incarcerated repeat offenders. The purpose of this study is to identify the reoffending risk of a sample of incarcerated male offenders with previous incarceration record based on their anticipation of reoffending. Using a self-reported methodological design, 351 incarcerated violent and nonviolent offenders are sampled. A number of self-anticipated reoffending risk factors are identified. The offenders’ age, illicit drug use, pro-offending attitudes, negative self-perception, familial detachment, deviant peer influence, poor prosocial attachment, and domestic and community criminogenic exposures are found to have significant predictive effects on their self-anticipated reoffending risk. Implications for intervention strategies with emphasis on these risk factors are discussed.