Research has shown that more efforts are needed to increase high school completion and postsecondary enrollment among Latino youths. However, little is known regarding efforts that engage both Latino youths and their parents. To address this gap, we surveyed Juntos Oregon participants to examine the school and community context Latino youths and their families face in the educational journey and identify effects of the Juntos program. Results showed that in a context of persistent discrimination and unfair treatment, Juntos workshops increased the sense of school and community connectedness among Latino parents. Increases in academic planning and motivation occurred as well. Extension may increase its educational impact by strengthening connections and promoting engagement between schools and Latino families.