Background: The purpose of this study was to examine the prospective associations between 17 individual, family, and community level youth assets and truancy among adolescents living in 1-parent and 2-parent households. Methods: Five waves of data were collected annually over a 4-year period from a racially/ethnically diverse sample of adolescents (N = 722, 51.5% female, mean age = 14.1 years). Generalized linear mixed models were used to identify prospective associations between youth assets and truancy while stratifying by family structure and controlling sociodemographic characteristics. Results: Five of the 17 youth assets were significantly associated (p < 0.05) with reduced odds of truancy among adolescents living in 1-parent households compared to 10 of 17 assets for adolescents living in 2-parent households. The significant asset/truancy associations were stronger for adolescents living in 1-parent households, whereas for adolescents living in 2-parent households, more of the community assets were significantly protective (p < 0.05) from truancy. Conclusion: Assets that focus on supporting adolescents' future aspirations and expectations may reduce truancy among those living in 1-parent households, whereas assets that promote community involvement and increased interaction with teachers and peers may protect adolescents living in 2-parent households from truancy.