Previous research indicated a significant role of family variables (parental supervision and attachment) in the study of criminality. Social learning of criminal behaviour suggested that the intensity of criminal acts during adolescence is predicted by exposure to criminal peer groups. Based on a sample of recidivists (n = 312) incarcerated in a high-security prison, this article investigates the direct and indirect effects of parental attachment, parental supervision, and peer relations on associations with criminal friends and subsequent criminal behaviour. Two alternative models of criminal behaviour were specified and estimated in Mplus 6 with restricted maximum likelihood estimation, using structural equation modelling. Results suggest that parental attachment has a significant, positive direct effect on parental supervision and relationships with peers, and an indirect effect on associations with criminal friends via parental supervision. Results also indicate a direct negative effect of parental supervision on criminal associations and a strong, positive effect of criminal associations with criminal friends on criminal behaviour. The only indirect predictor of criminal behaviour was parental supervision via associations with criminal friends. Further implications in relation to theory and previous studies are discussed.