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GST’s basic argument that strain can pressure individuals into committing crime has received much empirical support. However, the theory’s mediating hypothesis (i.e., negative emotion) and moderating hypothesis (i.e., various individual and environmental characteristics) have received less strong and less consistent support. These two components of the theory are usually tested as discrete phenomenon by testing the relationship between strain and crime for mediation (via negative emotion) or by testing the relationship between strain and crime for moderation (by various individual and environmental characteristics). However, Agnew has suggested that individuals’ emotional response to strain may itself be conditioned by various factors, and the moderating hypothesis as commonly interpreted implies that the relationship under consideration is not between strain and crime, but rather between the emotional response to strain and crime. Taken together, these three processes suggest that the effect of strain on crime may operate through a process of moderated mediation, whereby the mediating effect of negative emotion is moderated by various individual and environmental characteristics. We test this proposition using individual- and community-level data from the Project on Human Development in Chicago Neighborhoods. The results expand our understanding of the mechanism by which strain can pressure individuals into crime.