What medical expenses are HSA eligible?

The rule of thumb: if it diagnoses, treats, or prevents a medical condition, it almost certainly qualifies - and the IRS master list (Publication 502) is longer than most people expect. The everyday yeses: doctor and specialist visits (in-person or telehealth), urgent care and ER, prescription drugs, over-the-counter medicines and menstrual care products - both qualified since 2020, as Publication 969 notes - dental work and cleanings, eye exams, glasses and contacts plus solution, mental health therapy and psychiatry, lab tests and imaging, medical equipment from crutches to blood-sugar monitors, chiropractic and physical therapy, and smoking-cessation programs. Travel to get medical care, at a per-mile rate, even qualifies. The common noes catch people out: health insurance premiums (with narrow exceptions like COBRA and Medicare premiums in retirement), gym memberships and general wellness, cosmetic procedures, vitamins taken for general health rather than a diagnosed deficiency, and anything you were already reimbursed for by insurance. Using HSA money for a non-qualified expense before 65 means income tax plus a 20 percent penalty - after 65, the penalty drops away and it works like a retirement account, so the stakes are real but the boundaries are forgiving once you know them. When in doubt, the test is medical purpose, and Publication 502 answers almost every edge case. Pymander is a free AI doctor, 24/7 by text, and can help you sanity-check a specific expense.