To determine associations between menopausal status, reproductive hormone levels, menopausal symptoms, and poor sleep quality. The present study examines subjective sleep quality over an 8-year period in participants in an ongoing longitudinal study of ovarian aging in a randomly identified cohort of African American and Caucasian women. The Penn Ovarian Aging Study, a population-based cohort of 436 women from Philadelphia County who were 35 to 47 years of age and had regular menstrual cycles at enrollment. N/A. The primary outcome measure was the Sleep Quality factor score, derived from the St. Mary's Hospital Sleep Questionnaire, which was adapted for this population and collected at each assessment period over the 8-year follow-up. Associations between menopausal status, reproductive hormone levels, menopausal symptoms, sleep quality, age, and race were examined in multivariable linear mixed regression models for repeated measures. Menopausal status was not significantly associated with sleep quality (P = 0.12). In the adjusted model, independent predictors of sleep quality were hot flashes (P < 0.0001), Center for Epidemiological Studies Depression Scale scores (P < 0.0001) and levels of the reproductive hormone inhibin B (P = 0.05). Sleep quality was predicted by hormone levels and symptoms that occur in the menopausal transition but did not worsen with advancing menopausal status alone. Lower inhibin B levels, hot flashes, and symptoms of depression were all strong and independent predictors of difficulty sleeping. Race was not a significant contributor to sleep quality. Together, the findings demonstrate that women who experience other perimenopausal symptoms are likely to experience sleep problems during the menopausal transition.