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What clients miss about HSAs — and how advisors can help

Kathryn Miller at Financial Planning wrote about what clients miss about health savings accounts: the covered expenses go well beyond copays and dental, into physical therapy, chiropractic care, mental health treatment and, with a doctor's letter, things like air purifiers and fitness programs.

My contribution was the boundary. An HSA is not a wellness fund. Cosmetic procedures are almost always denied on audit, and the account holder faces a penalty on top of the full amount being treated as taxable income. The same procedure can go the other way: Botox to correct a deformity or treat a documented medical condition qualifies, while Botox for appearance does not. The line is medical necessity, not medical-adjacent.

The overlooked expenses I pointed to: therapy and counseling, acupuncture, a slice of long-term care insurance premiums on a sliding scale by age, and even home modifications like a ramp if medically necessary. The real boundary is the test itself. Not "Is this health related?" but "Is this primarily for the diagnosis, treatment, cure or prevention of a condition?"

For clients who let an HSA grow for retirement, that test matters twice: once when the expense happens, and again years later when they reimburse themselves tax-free and need the receipt to prove it.

Read the full article at Financial Planning →

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Jeff Judge Managing Partner
Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.
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