ObjectiveThis cross-sectional survey study investigated the association between family cumulative risk and meaning in life among Chinese secondary vocational school students, examining the mediating role of self-esteem and the moderating role of labor education support perception.MethodsA questionnaire survey comprising the Family Cumulative Risk Scale, Meaning in Life Questionnaire (MLQ), Rosenberg’s Self-Esteem Scale (RSES), and Labor Education Support Perception Scale (LESPS) was administered to 1536 secondary vocational school students from various grades.ResultsFamily cumulative risk was significantly and negatively associated with meaning in life (β = –0.34, p < 0.001), and the indirect association through self-esteem was significant. Labor education support perception, assessed using a newly developed scale with preliminary psychometric support, moderated the theoretically specified associations between family cumulative risk and self-esteem, and between self-esteem and meaning in life. Specifically, the negative association between family cumulative risk and self-esteem was stronger at higher levels of labor education support perception, consistent with the “drop in the bucket” model, although alternative explanations are also possible. The positive association between self-esteem and meaning in life was weaker at higher levels of labor education support perception, consistent with the “exclusion hypothesis.”ConclusionFamily cumulative risk was negatively associated with meaning in life, partially through lower self-esteem, and the strength of this indirect association varied as a function of labor education support perception. These findings identify a theoretically meaningful pattern of associations and highlight the importance of strengthening context-specific school-based support that helps secondary vocational school students develop self-esteem, construct positive vocational identities, and perceive their future work as meaningful.