Recently developed inmate behavior frameworks have expanded the discussion from deprivation/importation models to a life-course perspective. DeLisi and associates (International Journal of Offender Therapy and Comparative Criminology 55;1186–1207, 2011) presented the life-course importation model of inmate behavior based on a sample of state incarcerated offenders; however, their analyses were unable to distinguish indirect and direct effects of delinquent career and distal family background factors. The current study builds on the life-course importation model of inmate behavior by using path analysis to understand the direct and indirect effects of distal pre-incarceration indictors on gang-related inmate misconduct for 2,520 incarcerated youthful offenders. The findings lend support to the life-course importation model as the familial gang indicator was associated directly with individual gang affiliation, gang affiliation was associated directly with gang-related misconduct, and familial gang associations was associated indirectly with gang-related misconduct.