Innovation in English as a Second Language (ESL) services to support Latino immigrant parents and their children is needed, and this study examines a novel program that suggests future directions for the field. The Community Action Project of Tulsa County, Oklahoma's two-generation ESL program recruits parents of children enrolled in Head Start and delivers an ESL curriculum that is contextualized to child development and children's early school experiences. This mixed methods study explores the progress and the perspectives of parents and staff in this ESL program over two semesters (n = 35). Among enrollees in each semester, parents had high levels of completion (83% in semester 1; 70% in semester 2) and class attendance (94% in semester 1; 88% in semester 2). Yet, only about half (46%) of the parents completed both semesters 1 and 2. Parents who completed either semester 1 or semesters 1 and 2 did exhibit advancement in their English language skills, moving on average from beginner ESL levels to high intermediate levels based on National Reporting System benchmarks. Data from focus groups with parents and staff suggest that involvement in a two-generation ESL program can support parents' focus on their children, including: (a) alignment of parent curriculum with child development, (b) bidirectional parent and child learning, and (c) an improved sense of parent agency with their children's schooling and other child-related domains. Implications for future two-generation ESL programming are discussed. (author abstract)