With increasing percentages of the population in retirement, or approaching retirement, it is important to better understand how an individual's health and well-being may change during the retirement transition and for whom this transition may be particularly beneficial or problematic. Toward this end, the present study evaluated borderline personality disorder features as predictors of well-being and health trajectories from pre-to-post retirement, using up to seven waves of longitudinal data from the St. Louis Personality and Aging Network study. Participants were 590 older adults (aged 55-65, M = 60.6 at baseline) who retired over the course of their participation in the study (55% women, 45% men; 65% White/Caucasian, 32% Black/African American). Nonlinear change models were used to assess participants' patterns of life satisfaction, physical functioning, and depressive symptoms throughout the retirement transition. Results showed that older adults with higher borderline personality disorder features tended to report worse well-being and health in general. However, counter to expectations, there was limited evidence suggesting that the retirement transition yielded differential trajectories for health and well-being based on borderline personality disorder features. Notably, there were modest moderation effects observed for depressive symptoms. Key findings are discussed in terms of how the current work contributes to the field's existing understanding of retirement as a significant life transition affecting personal well-being.