Much of the criminological literature testing rational choice theory has utilized hypothetical scenarios presented to university students. Although this research generally supports rational choice theory, a common criticism is that conclusions from these studies may not generalize to samples of actual offenders. This study proceeds to examine this issue in two steps. First, a traditional sample of university students is examined to determine how various costs and benefits relate to their hypothetical likelihood of offending. Then the same data collection procedures are employed with a somewhat different sample of younger, adjudicated, and institutionalized offenders to determine whether the conclusions drawn from the student sample generalize to this offender sample. Results generally suggest that the content and process of hypothetical criminal decision making differ in the sample of known offenders relative to the university students. Limitations of the current study, as well as suggestions for future research, are discussed.