Is the High-Deductible, Health Savings Account Medical Plan Right for You and Your Family?

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For many, your airline benefits open-enrollment period is quickly approaching. You will have many choices during this annual open enrollment and this article addresses one of the most important choices of all; what type of healthcare plan is right for you and your family? More specifically, we’ll discuss the pros and cons of the high-deductible health plan (HDHP) paired with the Health Savings Account (HSA). 

A Health Savings Account is what the name implies: a tax-advantaged savings account used for healthcare expenses. The HSA account is like no other investment account because it is the only one that offers triple tax savings.

  1. Contributions to a Health Savings Account (HSA) are tax deductible.
  2. For example, if you are in the 24% marginal tax bracket, married filing jointly, and you maximize your HSA annually, your tax savings could be $2,052 ($8,550 x 0.24).
  3. You can invest the contributions to your HSA and they grow tax-free, similar to a 401(k) or IRA.
  4. Depending on the employer, HSAs typically require a minimum balance of $2,000 before allowing investment of additional funds.
  5. When monies are withdrawn for qualified medical expenses, there is no tax due on the distribution.  Note: There could be a 20% penalty and taxes for using the HSA for non-qualified expenses.
  6. If you withdraw funds from the HSA after you turn 65, you will not be penalized for non-medical expenses. For example, you could use your HSA to purchase a car at age 65, but you will owe ordinary income taxes, similar to a pre-tax 401(k)/IRA distribution. 

Possible HSA strategy

Many people (including me) plan to use the HSA as a medical 401(k). Consider saving the maximum annual amount and only withdraw monies for large medical expenses you can’t cover with your regular cash flow. Qualified medical expenses still count towards your annual deductible, whether you used the HSA or out-of-pocket cash to pay the expenses. This strategy allows the most savings, investing and tax deferral to work for you over time. 

Log Your Expenses and Save your Receipts!

Be sure to save all medical-expense receipts regardless of whether you use your HSA or out-of-pocket cash to pay. Even years later, since the IRS does not impose a time limit, you may reimburse yourself tax-free from your HSA for the qualified medical expenses you paid out-of-pocket. This strategy not only preserves the tax advantages of the account but also creates a reserve of reimbursable expenses that can be tapped in the future. In the event of an unexpected non-medical emergency, you could withdraw funds from your HSA tax-free by matching them to unreimbursed medical receipts.

Here is a short list of typically eligible medical expenses that qualify to be paid from the HSA:

  • Prescriptions and medications
  • Dental work
  • Vision care
  • Over-the-counter drugs and medical supplies
  • Preventative care
  • Physical therapy, chiropractic and psychiatric care
  • Medicare premiums
  • Long-term-care premiums

Here is a short list of non-eligible medical expenses

  • Cosmetic surgery
  • Medical insurance premiums: exceptions noted above
  • Vitamins

For a more detailed listing of eligible expenses see IRS Publication 502. 

 

The Numbers: HDHP and HSA Details

After enrolling in your airline’s HDHP, your contributions to an HSA are immediately vested and can be made by both you and your employer. Your new HSA is also portable; in case you’re worried about an employer change in the future. The 2025 annual contribution limit is $4,300 if single, $8,550 if married. Individuals aged 55 and older may contribute an additional $1,000 annually as a catch-up contribution.

Are the HDHP and HSA Right for You?

Although HSAs have great tax savings attributes, the most important factor in your decision on whether to select a High-Deductible Health Savings Plan is your current medical circumstances.  Below are a few factors to consider when determining whether an HDHP and HSA are right for you:

  • Health History
  • If your family’s health circumstances require frequent doctor visits or ongoing treatment, dealing with the higher and consistent out-of-pocket costs for care associated with the HDHP may be too much of a burden on both your finances and peace of mind.
  • Health Care Coverage
  • To contribute to an HSA, the IRS requires that you be exclusively covered by an HDHP. Examples of disqualifying coverage include TRICARE or Medicare. (I.e., if you use TRICARE as primary or backup healthcare, you cannot contribute to an HSA.)

Important note: For Medicare specifically, there is a lookback period of coverage for six months prior to enrolling, meaning you cannot contribute to an HSA for that period.

  • VA Medical Benefits
  • You may be temporarily ineligible to contribute to an HSA if you have received Veterans Affairs medical benefits within the past three months.

Okay, so HSAs are great and could be helpful if they fit with what you need. Fantastic. That said, there are a few important considerations you should be aware of, apart from the bullet points mentioned above.

  • Paperwork
  • Besides filing the IRS Form 8889 with your tax return, the IRS recommends keeping receipts for medical services and evidence of whether or not you were reimbursed. The lookback period for an audit can extend up to seven years, so there’s a bit of due diligence that’s required for keeping track of everything.
  • Penalties for Non-Medical Use
  • If you find yourself needing to dip into your HSA for non-medical expenses, you’ll be penalized. On top of income tax being subtracted from the amount you withdraw, the IRS excises a 20% penalty.

HSAs May Be Worth the Effort … or Not!

If you’re weighing the decision, remember that HSAs are best used as a long-term strategy. They reward patience, diligent tracking, and the willingness to take on some risk for long-term gain. If the paperwork and potential out-of-pocket expenses seem manageable, and you like the idea of combining retirement planning with tax-advantaged healthcare spending, then opening an HSA this enrollment season may be a smart move. If not, that’s fine too. The best plan is the one that gives you peace of mind and helps you sleep at night.


Charles Mattingly, MBA, CFP® | CEO & Lead Planner

Leading Edge Financial Planning

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Leading Edge Financial Planning LLC (“LEFP”) is a registered investment advisor. Advisory services are only offered to clients or prospective clients where LEFP and its representatives are properly licensed or exempt from licensure. For additional information, please visit our website at www.leadingedgeplanning.com. The information provided is for educational and informational purposes only and does not constitute

investment advice, and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status, or investment horizon. You should consult your attorney or tax advisor. The views expressed in this commentary are subject to change based on market and other conditions. These documents may contain certain statements that may be deemed forward-looking statements. Please note that any such statements are not guarantees of any future performance, and actual results or developments may differ materially from those projected. Any projections, market outlooks, or estimates are based upon certain assumptions and should not be construed as indicative of actual events that will occur. All information has been obtained from sources believed to be reliable, but its accuracy is not guaranteed. There is no representation or warranty as to the current accuracy, reliability, or completeness of, nor liability for, decisions based on such information, and it should not be relied on as such.




SOURCEAero Crew News, September 2025
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Charlie Mattingly
Charlie Mattingly, a CERTIFIED FINANCIAL PLANNER™ professional, is a first officer for one of the "big 4 airlines," based in Atlanta. Charlie and his team of dedicated professionals specialize in helping pilots create, grow and protect their wealth so they can have as much fun in retirement as they did flying airplanes for a living. Originally from Louisville, Kentucky, Charlie earned his Bachelor of Science degree in Mechanical Engineering from the University of Tennessee in 1997. He then served with the United States Air Force for ten years as an officer and F-16 fighter pilot. While serving in the Air Force, Charlie shared his passion for personal financial planning by administering Dave Ramsey’s Financial Peace University to his fellow military servicemen and women. After the Air Force, Charlie wanted to begin a new career helping others understand and thrive in personal finance which drove him to earn his MBA in Financial Planning from California Lutheran University. Charlie also received the CERTIFIED FINANCIAL PLANNER™ (CFP®) professional designation in 2012. Charlie’s passion is to understand each client’s unique situation and their family’s goals and dreams for the future. His objective is to take the worry out of personal finance. He works hard to be worthy of his clients’ trust, providing absolute transparency, a high level of integrity and objective advice. Charlie believes his prior life and work experiences as an Air Force officer and pilot have helped him understand the discipline, knowledge and leadership it takes to be an effective financial advisor for his clients. Charlie was hired by the airlines in 2007 and is fortunate to have the flexibility to continue to fly for the same company today. Charlie commutes to Atlanta from his home in Maryville, Tennessee where he enjoys spending time with his wife Leisa and their three beautiful girls Emma, MaryJo and Ellison. In his spare time, Charlie loves to read, play golf and even sometimes pretends to be a horse farmer!

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