Late life involves a variety of different challenges to well-being. This study extends upon and qualifies propositions drawn from the paradox of well-being in aging using 15-year longitudinal data on depressive symptoms from old and very old participants in the Australian Longitudinal Study of Ageing (at baseline n = 2,087, M age = 78.69 years, range = 65-103 years; 49.40% women). We first examined age-related trajectories in depressive symptoms from young-old to oldest-old, taking into account (changes in) relevant correlates, pathology, and mortality, and, second, investigated gender differences in these trajectories. Results revealed that age-related trajectories of depressive symptoms were indeed predictive of mortality hazards. The unique predictive effects of both level of, and change in, depressive symptoms were independent of one another and hold after taking into account education as well as changes in marital status, living arrangements, cognitive function, and illness burden. In addition, results indicated that depressive symptoms were elevated among participants suffering from arthritis, and increased with age more markedly in men than in women. In particular, the significant age by gender interaction indicated that the gender gap in depressive symptoms reduced from young-old to oldold and reversed in very old age when men showed more depressive symptoms than women.Qualifying the paradox of well-being in aging, findings demonstrate that depressive symptoms increased from young-old to oldest-old and suggest that age-, pathology-, and mortality-related changes should be examined in concert to advance our understanding of individual differences in Late life involves many challenges with consequences for changes in well-being (Baltes, 1997; Berg, 1996; Birren & Cunningham, 1985). Yet, in contrast to age-normative declines in physical health and cognitive functioning, a myriad of studies provide empirical evidence of a relative stability or even improvement in well-being in old age (Charles & Carstensen, 2010; Charles, Reynolds, & Gatz, 2001;Mather, 2012;Mroczek & Kolarz, 1998). This preservation of well-being despite age-related losses has been coined "the stability paradox of well-being in aging" (Kunzmann, Little, & Smith, 2000;Mather, 2012). From our perspective, however, the empirical evidence for the paradox has three important limitations. First, evidence mostly concerns age-related changes in the cognitive component of subjective well-being (e.g., life satisfaction; Diener, Suh, Lucas, & Smith, 1999;Gana, Bailly, Saada, Joulain, & Alaphilippe, 2013), whereas results regarding age-related changes in affective components of subjective wellbeing are less clear (Schilling, 2006). Second, the well-being paradox may hold only until early old age and less is known about life periods for which major loss experiences are frequent such as old-old and oldest-old age (Baltes & Smith, 2003). Third, a major challenge for research examining age-related changes in well-being pertains to the fact that ...