Prison violence has been a foundational concern within criminology, with previous research showing institutional factors and antisocial attitudes and behavior as among the most consistent predictors of prison misconduct. The current study used structural equation modeling to explore how inmate characteristics, inmate attitudes, self-control, affective experiences of prison such as perception of the environment, participation in inmate economy, and witnessing victimization predicted serious prison misconduct among 208 male inmates of a work-release facility. Survey questionnaires collected data on self-control, perceived prison environment, criminal attitudes, offending, and control measures. The analysis focused on a sequential model of the specific mechanisms of importation of offender characteristics into prison and their effect on prison life, and ultimately, prison misconduct. Results of structural equation modeling indicated support for lifestyle-exposure theories of prison misconduct and suggested that both the importation and deprivation models of inmate behavior are salient in the explanation of prison misconduct when their effects are understood as mediated by the inmate’s lifestyle while imprisoned. Participation in the inmate economy was singled out as the most significant predictor of prison misconduct. Continued research attention on the lifestyle characteristics of inmates is warranted for their effects on various facets of prison life. Tables, figures, references