Asian immigrant parents often expect their children to pursue higher education and to succeed academically; this may be reinforced as parents lose social status upon arrival to the host country. In response, Asian immigrant youth often experience psychological distress and alienation from their parents. We studied Asian immigrant youth’s exposure to parental expectations and parents’ struggles post-migration to Canada, in conjunction with Asian immigrant youth’s career and academic choices and level of distress. Forty-nine first- and second-generation Asian immigrant university students from a single Canadian university institution completed an on-line survey assessing their migration trajectory, parents’ expectation and influence in choosing their field of study, and distress. Parental difficulties and participants’ awareness of those were highly correlated with perceptions of high parental expectations and filial piety. Whereas second-generation youth focused more on how they received direct pressure from parents to succeed according to parental standards, first-generation youth placed higher emphasis on how their own awareness of parental difficulties acted as a source of internal motivation. The average depression score of first-generation respondents was significantly higher than that of second-generation respondents, and association between family’s financial struggle and guilt was observed. This study provides insight on possible contributors to distress in Asian immigrant youth related to parental expectations and struggles post-migration.