Research grounded in self-determination theory confirms the importance of different types of work motivation for well-being and job performance. Less is known about the role of work motivation at the end of one's working life and its association with adjustment to retirement. We investigated the association between preretirement work motivation and retirement adjustment in a subsample of the Health, Aging and Retirement Transitions in Sweden (HEARTS) study. We included participants (n = 572) who retired between two annual waves in this longitudinal study. Retirement adjustment was operationalized as change between waves in satisfaction of the three basic psychological needs (autonomy, competence, and relatedness). The association between preretirement work motivation and retirement adjustment varied depending on the subdimension of motivation (intrinsic, identified, introjected, external, or amotivation), type of transition (full vs. partial), and the particular need (autonomy, competence, and relatedness). In line with our expectations, low intrinsic work motivation was associated with gains in autonomy satisfaction for full-time retirees, which may be interpreted as a relief from dissatisfying jobs. Among those who continued to work, high intrinsic motivation was related to increases in relatedness satisfaction, that is, retirees who were intrinsically motivated for their work seem to benefit from continuing to work in retirement. In contrast to our expectations, amotivation before retirement was associated with gains in relatedness satisfaction for those continuing to work. Our results highlight the complexity of retirement and the need to study postretirement adjustment as a multifaceted and multidirectional process.