This study investigated the relationship of perceived financial stress and strain within the family with work hope beliefs among 119 adolescents in the United States. As expected, higher levels of perceived financial stress and strain related to lowered work hope. Using a test of moderation, we explored how this relationship was influenced by adolescents’ perceptions of support for educational success from their primary caregiver. Results indicated that caregiver support for educational success moderated the relationship between perceived financial stress and strain and work hope such that the negative relationship between financial stress and strain was strengthened among those who reported heightened perceived caregiver support for educational success. Limitations and implications for research and practice are discussed.