While strain theory at one time occupied a prominent position in criminology, it currently lurks near the fringes of criminological theory. Although Agnew’s (1992) focus on general strain theory has sparked renewed interest in strain theory, there has been little empirical study of the contextual effects described in traditional and contemporary strain theories. The current study explored whether opportunity structures lead to different outcomes, including delinquent outcomes, as specified by strain theory. Data were drawn from the National Education Longitudinal Study, which collected data every 2 years from 1988 to 1994 from a nationally representative sample of eighth grade students enrolled in private and public schools. The current analysis was based on responses from 12,421 students from 883 schools. Individual-level measures included delinquency during both years of the survey and demographic control variables. School-level measures for assessing opportunity structures included within school delinquency, student values concerning delinquency, and school quality. Results of statistical analyses indicated mixed support for aspects of both traditional and contemporary strain theories; specifically, changes in stressful life events were significantly related to changes in delinquency across the study period. The findings also revealed that the disjunction between educational expectations and future economic aspirations was associated with greater delinquency involvement over time and strain was found to negatively impact self-concept over time. The impact of stress or strain on delinquency, however, did not vary across opportunity structures. Future research should focus on additional contextual measures of access to illegitimate opportunities. Tables, references