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Due to a defaulted “continuation” approach to postgraduate education, whether college graduates delayed the investment in response to the labor market remains poorly understood. This speaks highly relevant for underemployed individuals holding jobs that do not require BA expertise, given that postgraduate education may help enhance the job prospect. Pooling two longitudinal datasets from National Survey of College Graduates, this study examines whether underemployment pushes individuals to pursue postgraduate education. Preliminary findings suggest that, although underemployed graduates face more unfavorable occupational contexts and lower job quality that positively shape the investment, they are less likely than adequately employed workers to pursue, net of controls. Unequal postgraduate investment by underemployment status raises concerns for widening economic inequality in the long run.