We analyze school attrition among youth in Kanchanaburi province, Thailand. We find that family investments in schooling are shaped by both household and local community contexts. There is an enrollment advantage for girls across different households and communities. We find that youth whose mothers have migrated and youth in immigrant households are at greater risk of leaving school. Attrition is negatively associated with household educational and economic resources. The local labor market, especially the supply of professional and managerial work, positively affects family investment in children's education. For girls, but not boys, the odds of leaving school are lower in communities dominated by manufacturing and services occupations, which disproportionately employ young women. Our findings highlight the obstacles to achieving universal secondary schooling completion in societies characterized both by entrenched inequalities as well as new inequalities brought about by uneven development, feminization of labor, migration, and other processes related to globalization. (Contains 6 footnotes, 3 tables, and 1 figure.)