This study examined the relationship between three midlife transitions and depressive symptoms among 952 women 50 to 59 years of age. Using longitudinal data from women interviewed for the 1992 and 2000 Health and Retirement Study, the study described changes in marital status, change to a parental caregiving role, and changes in perceived health across the eight years. Further, it examined the impact of these changes on mental health. The findings indicate that becoming widowed, becoming a caregiver, and perceiving health declines significantly increased depressive symptoms in the year 2000, even when controlling for pre-transition levels of depressive symptoms. The findings are consistent with the lifecourse perspective that individual development occurs in context and across the lifespan. The findings confirm and add to current midlife research literature.