Oura Ring 4 Silver Smart Ring, Exclusive Bundle, Ring + Additional Charger Included

Yes, when you buy it primarily to help diagnose, treat or prevent a specific condition, not for general fitness or wellness (IRS FAQ Q15). No letter is required: pay with your HSA or FSA card.

No letter is required. What makes a wearable a medical expense is why you buy it: primarily for a specific condition. A clinician's recommendation, your symptoms, a diagnosis, abnormal test results or risk factors all count; a general wish to track or improve your health does not.

Maybe — LSA coverage is set by your employer's plan, so it varies by person. Caeli reads your employer's LSA categories and tells you whether you can pay this way — often with no paperwork. If you have both an LSA and an HSA, Caeli steers you to spend the LSA first (it can expire) and protect the HSA (it compounds).