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Retirement can be difficult, and experiences vary greatly. Although health, financial status, and family responsibilities have been associated with retirement adjustment, individual psychosocial characteristics may also play a role. Moreover, relatively little is known about the impact of perceived “job lock”—the belief that retirement is impossible due to financial or health constraints—and its relationship with later retirement adjustment. The current study addresses these limitations in the literature by examining the retirement transition over 4 years in a large sample of United States adults, with a particular focus on the ways in which personality may affect this transition. Data collected at baseline (2008/2010) and again 4 years later (2012/2014) included the Big Five personality traits, preretirement job lock, self-rated health, and multiple indicators of postretirement well-being, such as global and experienced well-being (anchored within activities in a single day). Participants were drawn from the Health and Retirement Study (HRS; N = 716; Mage = 61.9 at baseline). Results indicated that experienced positive affect was the only postretirement well-being outcome with a significant association with job lock, although only for those with low Conscientiousness. Findings also suggest that preretirement personality and subjective health play an important role for postretirement well-being. Thus, the current study highlights the importance for researchers and practitioners to consider both preretirement personality and health when evaluating individuals’ management of the retirement transition.