The FSA Christmas Gift Loophole Nobody Talks About

A middle-aged man in business casual clothing stands in a pharmacy aisle late at night, overloaded with an absurd number of health and wellness products stacked across his shoulders and arms. He looks wide-eyed and determined as items like braces, bottles, and therapy supplies spill out around him. A shopping cart beside him is already overflowing with more medical products under bright fluorescent store lighting.

You’ve got $500 in your FSA account. You’ve got twelve names on your Christmas list. You have two weeks before both deadlines are due.

And you’ve just discovered that massage guns, heating pads, and knee braces are all FSA eligible.

This isn’t coincidence. This is strategy.

What an FSA Actually Is (And Why It’s Not Ideal)

A Flexible Spending Account lets you set aside pre-tax dollars for medical expenses. Money comes out of your paycheck before taxes, which means you’re saving roughly 20-30% compared to paying with after-tax dollars. Smart, right?

Here’s the problem: FSAs operate on a “use it or lose it” model. Whatever you don’t spend by your plan’s deadline—usually December 31st—vanishes. Some employers offer a grace period until March 15th or allow a $640 rollover, but most people have no idea which option their plan includes until it’s too late.

Compare that to an HSA (Health Savings Account), which rolls over indefinitely, earns interest, and follows you from job to job. HSAs are objectively better. They’re retirement accounts disguised as healthcare spending. The money grows tax-free and never expires.

But HSAs require a high-deductible health plan. If your employer doesn’t offer one, you’re stuck with the FSA. And if the FSA is all your organization offers, that’s what you’ve got.

Which brings us back to December, that expiring balance, and the creative spending strategies people deploy to avoid donating their own money back to the system.

The Game Everyone Plays

December rolls around, the FSA balance is staring you down, and suddenly, everyone in your life develops medical needs that align perfectly with gift-giving.

Your spouse’s tight shoulders? Massage gun. FSA eligible. Merry Christmas.

Mom’s back pain? Heating pad—the nice one. FSA eligible. Happy holidays.

Dad’s blood pressure? Home monitor. FSA eligible. Festive.

Your running buddy’s knees? Compression sleeves. FSA eligible. ‘Tis the season.

You’re not buying Christmas gifts. You’re purchasing medical devices for people who happen to need them. The wrapping paper is purely coincidental.

The Mental Gymnastics Hall of Fame

Every justification sounds reasonable until you say it out loud.

“It’s not really a gift if they need it medically.” Sure. And that bottle of wine at dinner isn’t really drinking if you’re pairing it with food.

“I’m helping them prioritize their health.” Noble. Especially when that help arrives under a Christmas tree.

“They wouldn’t buy it for themselves.” Neither would they buy themselves socks, but we don’t pretend socks are medical devices.

“It’s not a gift, it’s an intervention.” Classic. Usually said while wrapping a posture corrector in Santa paper.

A bathroom medicine cabinet and linen closet are thrown open, completely stuffed with an absurd amount of last-minute FSA purchases. The medicine cabinet is jammed with thermometers, ointments, pill bottles, and gadgets no normal person needs three of, while the linen closet overflows with knee braces, back braces, yoga blocks, resistance bands, a TENS unit box, neck pillows, compression wraps, and enough therapy gear to outfit an entire physical therapy clinic. One lonely towel is squeezed into a corner like it lost the fight for shelf space. Harsh bathroom lighting makes the chaotic scene look even more real—capturing the comedy of someone panic-spending their remaining FSA dollars on “Christmas gifts.”

What’s Actually FSA Eligible (And Giftable)

Drop the pretense. Here’s your shopping list.

The Crowd Pleasers:

  • Massage guns ($50-400)—everyone’s shoulders hurt, nobody buys themselves one
  • Heating pads ($30-80)—your entire family has back pain they mentioned once
  • Foot massagers ($60-150)—universal truth: feet hurt

The “Thoughtful” Options:

  • Blood pressure monitors ($40-100)—says “I care about your longevity” and “you’re getting old”
  • Pulse oximeters ($25-50)—stocking stuffers that scream “I remembered COVID happened”
  • Digital thermometers in bulk—give one to everyone, call it a “family health kit”

The Fitness Adjacent:

  • Knee braces, ankle braces, wrist supports—does your recipient have joints? They qualify
  • Foam rollers—”I support your fitness journey” without requiring you to exercise with them
  • Compression socks—they come in colors now, fashion meets function meets FSA eligibility

The Self-Care Spin:

  • Blue light blocking glasses—anyone with a screen, which is everyone
  • TENS units—electric muscle stimulation for that person who “carries stress in their back”
  • Acne treatment kits—for your teenager’s “skincare routine”

The Line You Shouldn’t Cross

There’s gaming the system and there’s fraud. Know the difference.

Gray area but probably fine: Buying FSA-eligible items for people with genuine medical needs, even if you’re giving them as gifts. The item is legitimate. The recipient has the condition. The timing is convenient.

Actually problematic: Buying items for people with zero medical need just to drain the account. Healthy 25-year-olds don’t need blood pressure monitors. Toddlers don’t need compression socks.

Definitely fraud: Submitting reimbursement claims for non-eligible items or claiming purchases that never happened.

The massage gun for a spouse with documented shoulder tension? Efficient use of pre-tax dollars while being a thoughtful partner.

The massage gun for a coworker who mentioned stress once? That’s lying to the IRS.

Your December Checklist

Legitimate medical spending first:

  • Dental cleaning that’s been postponed
  • Year supply of contacts
  • OTC medications that actually get used
  • First aid supplies the kit actually needs

Gray area gift territory:

  • Massage equipment for people with actual muscle tension
  • Braces for people with joint issues
  • Monitoring devices for people with chronic conditions

Save receipts religiously. FSA administrators ask for documentation. “It was for mom’s back” isn’t a receipt.

Next year: Set a calendar reminder for October. Three months to spend strategically beats two weeks to spend creatively.

The FSA balance doesn’t care about anyone’s Christmas list. But when those two things happen to align?

That’s not fraud.

That’s December.


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