Over the last 70 years, oestrogen therapy for the management of menopausal symptoms has undergone a metamorphosis from perceived cardiovascular protection to perceived cardiovascular risk. The former perception is based on the very convincing evidence from the Nurses Health Study cohorts and the epidemiological data surrounding early menopause. The latter, and later, perception is based on the very disquieting results from the randomised controlled studies of Heart and Estrogen/Progestin Replacement Study (HERS) and the Women’s Health Initiative study (WHI). The reality is probably more nuanced than the conclusions presented by any of these studies. When face to face with a patient, the clinician must negotiate the appropriate decision pathway around the interaction between cardiovascular risk, cardiovascular disease, menopause, and oestrogen +/- progestogen containing hormone therapy. This presentation will attempt to do just that.