Since the earliest writings on immigrant adaptation scholars have speculated that assimilation may relate to delinquency through its effects on the family. Despite this longstanding line of inquiry, empirical research on family processes across immigrant generations has yielded equivocal findings, with some studies offering support for the mediating influence of the family on the assimilation-crime link, while others finding little variation across immigrant generations with respect to family functioning or its implication for behavior. Further, while research on immigrant adaptation has proliferated in recent years, consideration of how immigration relates to crime at the individual level has all but ignored the salient role of gender. The purpose of this research is to contribute to the growing literature on the individual level mechanisms linking immigrant status to offending behaviors in two important ways: First, using a diverse sample of youth from the Project on Human Development in Chicago Neighborhoods, I test the mediating role of five interstitial family processes--monitoring, attachment, support, harsh discipline and conflict--to determine whether generational differences in maladaptive behaviors are indeed attributable to differences in family characteristics. Second, I address a glaring gap in the immigrant-crime literature by examining the moderating influence of gender on the linkages among generational status, family processes and delinquency. Results of OLS and negative binomial regression analyses offer, at best, limited support for the hypothesized mediating role of family processes in the assimilation-crime link. For only one family process--family conflict--is generational status a significant correlate, net of controls. Sobel tests indicate that family conflict--which is higher among more assimilated youth--partially mediates the relationship between generational status and violence, but not substance use. Notably, however, I find important gender differences in the influence of assimilatory status on both family functioning and problem behaviors. Collectively, girls appear to be better "protected" by their immigrant status than boys. I discuss the implications of these findings and my proposed directions for future research.