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Grade retention is a common educational practice across OECD countries. Despite its widespread use, during recent years there has been a debate, both in policy and academic circles, concerning the effectiveness of this practice to remedy pupils’ learning deficits (Brodaty et al., 2013; Cockx et al., 2019; Eide and Showalter, 2001; Knipprath, 2013; Reschly and Christenson, 2013). While empirical research on the effect of grade retention on further academic attainment is abundant, the effect on labor market outcomes has rarely been studied. The aim of this study is, departing from queuing theory (Thurow, 1975), to examine the effect of retention in primary, secondary, and/or tertiary education on repeaters’ later labor market success. A field experiment was conducted, in which various treatments of grade retention were randomly assigned to 1,592 fictitious résumés sent in application to 796 real vacancies. We conducted this experiment between November 2014 and April 2015, applying for vacancies that were open for one of the following diplomas within the broad field of business: the secondary education degrees of (a) accountancy, (b) commerce, and (c) secretary-languages; the Bachelor degrees of (d) accountancy and tax, (e) finance and insurance, (f) legal practice, (g) logistics management, (h) marketing, and (i) SME management; and the Master degrees of (j) accountancy and taxation, (k) finance and risk management, (l) management and IT, (m) marketing management and (n) strategic management. The reactions of employers to our fictitious applications were received via email and mobile phone voicemail. Following Baert (2018), we defined a positive call‐back as the situation in which the applicant received (a) an invitation to a job interview concerning the job for which the candidate applied, (b) a proposal of an alternative position, (c) an inquiry to provide the employer with more information, or (d) an inquiry to contact the employer that reveals some interest. We also registered whether a temporary (versus permanent) contract and whether a part-time (versus full-time) contract was offered in the vacancy. Findings indicated that grade retention does not significantly affect positive call-back by employers. However, when narrowing in on vacancies for occupations where on-the-job training is important, job candidates with a record of grade retention are 16% less likely to receive a positive reaction, consistent with queuing theory. Based on these findings, we suspect that grade repetition is interpreted by employers as a sign of lower trainability. From a societal point of view, our findings indicate that anyone who repeated a year would do well to highlight their trainability when applying for a job. This can be done, for example, by emphasizing successfully completed training courses outside formal education or by explicitly signaling one’s own eagerness to learn. Moreover, if there is a reason for retention that has nothing to do with intellectual agility (and does not evoke any other stigma), it may be interesting to mention it in one’s motivation letter.