Thus far, research on perceived overqualification has focused on either maladaptive, strain-based versus more adaptive, self-regulatory reactions in isolation. Following person-environment fit theory, we seek to advance this one-sided focus by uniting both types of adjustment reactions and to consider their implications for perceived person-job fit, and performance and wellbeing outcomes. In line with theory, we also examine contextual boundary conditions in the form of indicators of formal work arrangements (i.e., permanent vs. temporary employment contract and job tenure). Utilizing three-wave data from 453 employees, we found that perceived overqualification indirectly and sequentially related to decreases in task performance, organizational citizenship behavior and job satisfaction via anger toward employment situation and lower levels of perceived person-job fit—thus reflecting the strain-based pathway. For the self-regulatory pathway, findings did not align with our initial proposition that the positive relationship between perceived overqualification and work organization (a form of structural job crafting whereby employees improve their work processes) would be weaker among temporary employees and those with longer tenure. Instead, having a temporary employment contract or having longer job tenure resulted in a negative relationship between perceived overqualification and work organization, which further contributed to a decrease in performance and satisfaction via lower levels of perceived person-job fit. Our study highlights the demotivating role of a temporary employment contract and long job tenure for overqualified employees to reorganize their work. In discussing our findings, we point to the importance of job stage and develop recommendations for managing overqualified employees.