We test two models in which Latina/o students' school connectedness partially mediates the relationship between barriers (discrimination experiences at school and other educational barriers, respectively) and thoughts of dropping out of high school. Results of a moderated mediator analyses in a sample of 896 Latina/o high school students were consistent with hypotheses. Latina/o students who reported greater frequency of discrimination experiences and those who reported greater frequency of other barriers that affect how they are doing in school were more likely to have thoughts of dropping out, and these relationships were attenuated by school connectedness. A hierarchical regression indicated that discrimination experiences, other educational barriers, and school connectedness each contributed unique variance to thoughts of dropping out. Findings highlight the salience of efforts to reduce discrimination in schools and enhance school connectedness as a potential protective factor for Latina/o youth. Implications for dropout prevention are discussed.