HRT/MHT prescribing requires careful risk-benefit assessment and monitoring. The WHI timing hypothesis: MHT initiated within 10 years of menopause or before age 60 provides net benefit (reduced mortality, cardiovascular protection, bone protection), while starting >10 years post-menopause increases cardiovascular and VTE risk. Risk assessment before prescribing: breast cancer risk (family history, BRCA status), cardiovascular risk, VTE history, liver disease, and migraine with aura (relative contraindication). Absolute contraindications: active/history of breast cancer, unexplained vaginal bleeding, active VTE/PE, active liver disease, known thrombophilia. Prescribing principles: lowest effective dose, shortest needed duration; transdermal preferred (lower VTE, gallbladder, triglyceride risk); progestin required if uterus intact (micronized progesterone preferred over synthetic progestins for metabolic and breast safety); vaginal estrogen for isolated genitourinary symptoms. Monitoring: annual breast exam/mammography, bleeding pattern assessment, blood pressure, cardiovascular risk reassessment, annual taper consideration.