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The recent integration and centering of sexuality in criminological research has elicited important findings regarding individuals’ sexual identities and their trajectory from offending through the criminal justice system. In particular, researchers have found that sexual minorities may have higher propensities toward criminal and delinquent activities as compared to same-gender heterosexual peers, especially for women. However, insufficient research has explored the mechanisms behind these disparate propensities. Under the framework of general strain theory, I investigate potential contextual factors that may increase daily strain for sexual minorities and consequently their propensity to commit crime, including rural residency (compared to urban or suburban) and Southern residency (as compared to other regions of the country). Additionally, for adolescents, I investigate whether the number and proportion of sexual minorities within their school predicts delinquency. I use data from the National Longitudinal Study of Adolescent to Adult Health, with multiple measures of sexuality for robustness (attraction, behavior, and self-identification), to predict the frequency of delinquent acts. I find that, while context matters in predicting this frequency, individual factors remain the strongest predictors of delinquency for heterosexual and sexual minority individuals alike.