HSA Strategy (Part 1)
Posted by Mark on August 14, 2025 at 06:57 | Last modified: February 24, 2026 12:22As mentioned in the second paragraph here, today I will begin discussing Health Savings Accounts (HSA) with the goal being how to invest mine.
Here is a legal disclaimer for the current blog mini-series.* This is not professional advice and not intended to replace the advice of a tax advisor or attorney. HSA contributions, distributions, and eligibility are IRS-governed and subject to change. As the account holder, you are responsible for verifying eligibility, tracking transactions, and complying with IRS regulations. While some HSA funds are FDIC-insured, investment options are not bank-guaranteed and may lose value. Information provided here is [mostly] accurate at time of writing but subject to change based on new legislation or IRS guidance.
Given that disclaimer, let me define HSAs as tax-advantaged personal savings accounts for individuals enrolled in high-deductible health [insurance] plans (HDHP).
HSAs offer the triple tax advantage:
- Tax-deductible contributions lower taxable income by corresponding amount.
- Tax-free growth means interest or capital gains on investment are not taxed [unlike tax-deferred 401(k) earnings].
- Tax-free withdrawals means proceeds used to pay for qualified medical expenses are not taxed.
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Upon turning 65 years of age, HSA funds may be withdrawn for purposes other than qualified medical expenses but taxed as regular income [like the 401(k)]. If used for purposes other than qualified medical expenses prior to age 65, then HSA funds are taxed as regular income and subject to a 20% penalty.
Qualified medical expenses (always keep receipts as documentation) are rather extensive:
- Medical services including ambulance services, doctor visits, hospital stays, laboratory fees, surgery, and X-rays.
- Dental and vision services including braces, cleanings, contact lenses, dentures, eyeglasses, fillings, and LASIK.
- Prescriptions and OTC (no prescription required) products including acne treatment, insulin, and menstrual products.
- Equipment and supplies such as bandages, blood sugar test kits, breast pumps, crutches, hearing aids, and masks.
- Acupuncture, addiction treatment, chiropractic care, physical therapy, psychiatric care, and smoking cessation programs.
- Capital expenses to accommodate disabilities (e.g. grasp bars, railings, and ramps).
- Costs for [primarily] medical-care transportation and related travel (i.e. mileage, tolls, parking, bus/airfare).
- Doctor-recommended special education (e.g. tutoring for children with learning disabilities due to mental impairment).
- Medicare (ages 65+) premiums (A-D) [can no longer contribute once Medicare-enrolled but may spend existing balance].
- Premiums paid for COBRA [medical, dental, and vision] continuation coverage if job lost to a qualifying event.
- Premiums paid while receiving federal or state unemployment compensation.
- Premiums paid for qualified long-term care insurance subject to age-based caps on annual tax-free withdrawal amount.
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I will continue next time.
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* — In case my buddy Marc (with a “c”) is out there reading