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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 four years in a large sample of U.S. adults, with a particular focus on the ways in which personality may affect this transition. Data collected at baseline (2008/2010) and again four years later (2012/2014) included the Big Five personality traits, pre-retirement job lock, self-rated health, and multiple indicators of post-retirement 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 ( N = 716; M age = 61.9 at baseline). Results indicated that experienced positive affect was the only post-retirement well-being outcome with a significant association with job lock, although only for those with low conscientiousness. Findings also suggest that pre-retirement personality and subjective health play an important role for post-retirement well-being. Thus, the current study highlights the importance for researchers and practitioners to consider both pre-retirement personality and health when evaluating individuals' management of the retirement transition. Word Count: 224.