Perimenopause, or the menopausal transition, represents a period of time during which newly arising symptoms can present complex management decisions for providers. Many women present to care with complaints of hot flashes, vaginal and sexual changes, altered mood and sleep, and changing bleeding patterns. The effect of these symptoms on quality of life, even before a woman enters menopause, can be significant. The appropriate evaluation and evidence-based management of women in this transition is reviewed in this article. Two case vignettes are used to highlight certain evaluation and treatment challenges.