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529 to Roth IRA: The Ultimate Rollover Guide (New IRS Rules for 2025!) – Don't Leave Free Money on the Table!

  529 to Roth IRA: The Ultimate Rollover Guide (New IRS Rules for 2025!) – Don't Leave Free Money on the Table! Alright, Future Millionaires and Master Budgeteers! Your favorite financial trainer is here, ready to drop some serious knowledge bombs that will make your wallet sing and your future self high-five you. Today, we're tackling a game-changer that's got the financial world buzzing: how to roll over those glorious 529 plan funds into a Roth IRA . Yes, you heard that right! The IRS, in a rare moment of what appears to be pure financial generosity, has cooked up some new rules for 2025 that could transform your leftover education savings into a powerful retirement war chest. Think of it like this: your college fund just got a superhero upgrade, and its new superpower is tax-free retirement growth . 🦸‍♀️💰 So, if you’ve been sweating about overfunding your kid’s 529, or if Junior decided that becoming a TikTok star was a more viable career path than a neurosurgeon (hey...

💸 What Can You Really Spend Your HSA Money On?



💸 What Can You Really Spend Your HSA Money On?

A Full List of Eligible Expenses (That'll Make You Say—Wait, That's Covered?!)

Let’s play a game:
What do sunscreen, pregnancy tests, acupuncture, and allergy meds have in common?
Give up?
They're all covered by your HSA—that magical unicorn of a financial tool that too many people severely underuse.

If you've ever asked yourself, "Can I really use my HSA for that?"—this post is your new best friend.
We’re diving deep into what counts as an eligible HSA expense, separating fact from fiction, and sprinkling in a little fun along the way.


🧠 First, a Quick Refresher: What’s an HSA?

An HSA (Health Savings Account) is a tax-advantaged savings account for people with a High Deductible Health Plan (HDHP) in the U.S.
It lets you:

  • Contribute pre-tax dollars 💵

  • Grow funds tax-free 📈

  • Withdraw money tax-free for qualified medical expenses 🏥

That’s a triple tax win, baby!

🌍 Heads up for global readers: While most countries don’t have HSAs, you may have something similar like Canada’s TFSA or the UK’s ISA. But they usually don’t cover medical expenses in quite the same way—or with this many perks.


🛒 So… What Can You Actually Buy With an HSA?

You’d be surprised how many everyday items are eligible. Let’s break it down by category:


🧴 Everyday Health & Wellness Products

  • Sunscreen (SPF 15+) – Protect your skin, protect your wallet

  • First aid kits – Because paper cuts are a thing

  • Menstrual products – Pads, tampons, cups (yes, all of them!)

  • Thermometers – Fever checks? Covered.

  • Contact lens solution – No more excuses for crusty lenses

  • Reading glasses & contact lensesLooking sharp, tax-free

✨ Pro Tip: Most of these can be bought using your HSA card at checkout on sites like Amazon or Walgreens — just look for “FSA/HSA eligible” labels.


💊 Medications & Treatments

  • Prescription drugs – You already knew this, right?

  • Over-the-counter meds (yes, with no Rx required now!)

    • Allergy meds

    • Pain relievers (Ibuprofen, acetaminophen)

    • Cold & flu remedies

    • Heartburn meds (Tums, Prilosec)

  • Smoking cessation products – Nicotine gum, patches, lozenges

  • Fertility treatments – IVF, egg storage, even sperm banking

  • Birth control – Pills, condoms, IUDs, and more


🧘 Alternative & Holistic Care

  • Acupuncture – Pinpoint your pain (and your savings)

  • Chiropractic care – Snap, crackle, tax-free

  • Massage therapy (with a doctor’s note) – Not just a spa day

  • Hypnotherapy (also with a note) – Even for smoking or stress!


🧍 Medical Devices & Services

  • Crutches, braces, and wheelchairs

  • CPAP machines & supplies for sleep apnea

  • Blood pressure monitors – Check yourself before you wreck yourself

  • Diabetic supplies – Glucose meters, test strips, insulin

  • Medical alert systems – Peace of mind, paid in pre-tax dollars


🧠 Mental Health & Therapy

  • Psychologist or psychiatrist visits

  • Licensed counselors – Including marriage and family therapy

  • Substance abuse programs – Rehab and recovery included

  • Support groups – If medically recommended

Mental health is health. Your HSA gets it.


👶 Pregnancy & Parenting

  • Prenatal vitamins

  • Breast pumps and lactation supplies

  • Childbirth classes (if for medical purposes)

  • Doula and midwife services (in many cases)

  • Baby monitors with medical features

💡 Tip: Check with your provider on specifics. Some expenses (like doulas) can be a grey area, but are often accepted with a doctor’s recommendation.


✈️ Travel & International Use

Yes, your HSA can go global with you… if you're careful.

  • Medical care abroad – As long as the provider is licensed

  • Travel expenses for medical care – Flights, hotels, and meals if you’re traveling over 50 miles for treatment

  • Medical tourism – Think: dental care in Mexico or eye surgery in India (if IRS-qualified)


🚫 What Doesn’t Count? (Nice Try, Though)

  • Cosmetic surgery (unless medically necessary)

  • Gym memberships (unless prescribed for a condition)

  • Vitamins (except prenatal or prescribed)

  • Toiletries, makeup, or beauty products

  • Pet care (even if Fluffy is your emotional support animal)


📱 Tools to Make It Easier

  1. WageWorks HSA Store – Shop for HSA-eligible products

  2. GoodRx – Compare prescription prices before using HSA cash

  3. IRS Publication 502 – The official guide to qualified medical expenses (a thrilling read… if you're into tax codes)

  4. ReceiptBank or Expensify – To track and store those tax-deductible expenses


🎬 Final Word: Your HSA is a Tax-Free Treasure Chest

If you’re just using your HSA for co-pays and checkups, you’re leaving money on the table — and nobody likes that.
You could be stocking up on everyday essentials, prepping for parenthood, investing in your mental wellness, or even planning future procedures abroad.

Maximize the power of your HSA — it's not just a savings tool, it's a lifestyle enhancer.


📚 Suggested Reading & Free Tools

  • [The Hidden Benefits of an HSA That Most People Overlook]

  • [Can You Use an HSA for Medical Tourism?]

  • [Bank of America HSA vs. Other Banks: Which One Offers the Best Perks?]

  • Free HSA Eligibility Checker Tool

  • IRS HSA Contribution Limits Calculator

  • HSA Shopping List Generator – Personalized by your health needs!



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