The current study investigated the relationships between self-esteem, personal and parental valuing of education, andacademic stress amongst two samples (sample sizes of 139 and 271, respectively) of undergraduates in Thailand.Multiple regression analyses revealed that self-esteem was the most powerful predictor of academic stress for bothsamples. While personal and parental valuing of education did not predict stress in either sample, in Sample 1, selfesteemmoderated the relationship between parental and personal valuing of education. Investigation of simpleregressions and scatter plots for the Sample 1 data indicated that parental valuing of education was the most influentialfactor in increasing personal valuing of education for students with low and average self-esteem. The differencesbetween the samples in terms of SES, geographic region, and university status are also discussed as possibleexplanations for the dissimilar findings across the two samples. The results are then contextualized in terms of Asianculture, and possible implications for research, policy, and practice are discussed.