Background: Two risk factors for negative outcomes in Latina/o youth are acculturation dissonance (i.e., discrepant family cultural orientations) and the endorsement of an assimilation strategy of acculturation (i.e., valuing dominant mainstream culture over culture of origin). Though these have been uniquely studied as risk factors for maladaptive behaviors among Latina/o youth, their interaction in relation to both externalizing and internalizing symptoms has yet to be fully examined. Objective: The present study examined the unique and interactive effects of acculturation dissonance and assimilation on both depressive symptoms and delinquent behaviors among Latina/o adolescents. Methods: Participants were 135 Latina/o adolescents (ages 14-20) recruited from a charter high school. Students responded to a paper-and-pencil survey assessing demographic information, acculturation strategy, acculturation dissonance, depressive symptoms, and delinquency. Results: Acculturation dissonance was uniquely associated with depressive symptoms, but interaction effects suggested this association depended on levels of assimilation. At high levels of assimilation, acculturation dissonance was not associated with depressive symptoms, since depressive symptoms were consistently high. In contrast, at low levels of assimilation, acculturation dissonance was positively associated with depressive symptoms. In contrast, acculturation dissonance was uniquely associated with delinquency, and this association did not depend on the level of assimilation. Conclusions: Dissonant cultural orientations within families of Latina/o youth confer risk for negative outcomes across internalizing and externalizing domains. For youth adopting an assimilation strategy of acculturation, risk for depressive symptoms may be increased. Implications of these findings and future directions are discussed.