This study examines the impact of three types of underemployment, i.e. level underemployment, content underemployment and contingent employment, on subsequent objective (i.e. salary) and subjective career success (i.e. job satisfaction) using a 10-year longitudinal dataset with 335 Dutch university graduates. Thanks to our longitudinal design, we were able to examine the impact of preceding underemployment and the specific timing of the underemployment in one’s career, in that way explicitly addressing the role of time in career success research. We tested our hypotheses through multilevel analyses. Level and contingent underemployment, but not content underemployment, were found to have a negative impact on future pay; whereas content employment, but not level or contingent underemployment, were found to affect job satisfaction five years later. In addition, for one type of underemployment (i.e., level underemployment), also the timing of the underemployment turned out to matter, indicating that the signal that level underemployment sends to employers may differ depending on when in one’s career it happens. Taken together, these findings point to the importance of using a path-dependency perspective when trying to understand people’s career success.