This phenomenological study examines Mexican immigrant parents' experiences of helping their children navigate and succeed in school and their perceptions regarding differences between the U.S. and Mexican educational systems. Findings highlight parents' challenges in helping their children succeed in a new and unfamiliar school system and the often serious implications for the success of their children. Challenges identified include language barriers, difficulties in understanding and dealing with unfamiliar rules, requirements and expectations for children, and feelings of ineptness in unfamiliar territory. Findings also highlight the importance of cultural resources in response to challenges. Educational and programming implications are discussed.