An increasing problem of great concern for academic institutions around the world is the pervasiveness of academic cheating among students. However, there is a dearth of prior research on cheating in cross-national contexts. The present study examines the relationships between structural measures of strain and principals’ reports of problematic cheating in schools across 35 nations, derived from the 2007 Trends in International Math and Science Studies survey. The study employs multilevel logistic regression analysis to evaluate whether indicators of economic disadvantage, educational achievement, and educational inequalities influence the level of problematic cheating reported by school principals cross-nationally. Additionally, we identify which socioeconomic and demographic characteristics of nation-states are most related to perceptions of problematic academic cheating as reported by school principals. The findings indicate that schools with resource shortages, greater levels of economic disadvantage, and those with larger national average grade sizes experience higher levels of problematic cheating.