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Vasomotor symptoms (VMS), encompassing hot flashes and night sweats, may be associated with diabetes, but evidence is limited. We sought to estimate these associations.Among 150,007 postmenopausal Women's Health Initiative participants from 1993 to 2014, we prospectively examined associations of incident diabetes with VMS characteristics at enrollment: any VMS, severity (mild/ moderate/severe), type (hot flashes/night sweats), timing (early [premenopausal or perimenopausal]/late [postmenopausal]), and duration. Cox proportional-hazards models estimated hazard ratios (HRs) and 95% confidence intervals (CIs).Mean duration of follow-up was 13.1 years. VMS prevalence was 33%. Reporting any VMS was associated with 18% increased diabetes risk (95% CI 1.14, 1.22), which increased with severity (mild: HR 1.13, 95% CI 1.08, 1.17; moderate: HR 1.29, 95% CI 1.22, 1.36; severe: HR 1.48, 95% CI 1.34, 1.62) and duration (4% per 5 years, 95% CI 1.03, 1.05), independent of obesity. Diabetes risk was more pronounced for women reporting any night sweats (night sweats only: HR 1.20, 95% CI 1.13, 1.26; night sweats and hot flashes: HR 1.22, 95% CI 1.17, 1.27) than only hot flashes (HR 1.08, 95% CI 1.02, 1.15) and was restricted to late VMS (late: HR 1.12, 95% CI 1.07, 1.18; early and late: HR 1.16, 95% CI 1.11, 1.22; early: HR 0.99, 95% CI 0.95, 1.04).VMS are associated with elevated diabetes risk, particularly for women reporting night sweats and postmenopausal symptoms. The menopause transition may be an optimal window for clinicians to discuss long-term cardiovascular/metabolic risk with patients and leverage the bother of existing symptoms for behavior change to improve VMS and reduce diabetes risk.