Poor sleep is one of the most common problems reported during menopause, and is known to vary throughout the menopause transition. The objective of this study was to describe the dynamics of poor sleep among participants of the Midlife Women's Health Study and to identify risk factors associated with poor sleep during the menopausal transition. Annual responses to surveys that included questions about the frequency of sleep disturbances and insomnia were analyzed to determine the likelihood of persistent poor sleep throughout the menopausal transition and the correlation of responses to the different sleep-related questions, including frequency of restless sleep during the first year of the study. Responses to questions about a large number of potential risk factors were used to identify risk factors for poor sleep. Poor sleep in premenopause was not predictive of poor sleep in perimenopause, and poor sleep in perimenopause was not predictive of poor sleep in postmenopause. Frequencies of each of the measures of poor sleep were highly correlated. For all sleep outcomes, high frequency of depression was related to a high frequency of poor sleep. Vasomotor symptoms were also significantly related with a higher frequency of all poor sleep outcomes. A history of smoking was also associated with higher frequencies of insomnia and sleep disturbances. The risk factors identified for poor sleep, depression and vasomotor symptoms, were consistently associated with poor sleep throughout the menopausal transition. The likelihood of these risk factors changed from premenopause, through perimenopause, and into postmenopause, however, which could explain changes in sleep difficulties across the menopausal transition. Treatment of these risk factors should be considered when addressing sleep difficulties in menopausal women.