The recent global economic downturn has stimulated a growing interest among scholars in how employees interpret and respond to the circumstance of being overqualified. However, the overqualification literature has been hindered by uncertainty regarding the extent to which employees’ perceptions of being overqualified are based in reality. The present study sought to address this concern by proposing and testing a theoretical model of objective overqualification, perceived overqualification, job satisfaction, and well-being using a cross-sectional sample of full-time employees who had recently graduated from college. Additionally, the present study investigated cognitive ability, achievement striving, and trait negative affectivity as potential moderators of several relationships delineated in the proposed model. Results indicated that the data were consistent with the proposed model, which argues that objective overqualification predicts employees’ perceptions of being overqualified, which creates feelings of relative deprivation and ultimately manifests in poorer job satisfaction and reduced well-being. Importantly, however, the pattern of relationships among study variables suggested that strain outcomes were mostly driven by perceived overqualification. Furthermore, employees’ perceptions of being overqualified appeared to be influenced considerably by unmeasured factors besides objective overqualification, potentially including dissatisfaction with other aspects of the job. There was no support for the hypothesized individual moderators. Overall, the study highlights the importance of taking a more nuanced approach to studying overqualification phenomena and cautions against the assumption that being objectively overqualified is a necessarily undesirable circumstance for individuals and their employers.