09/22/2026
🩺 Medicare mistakes don't all work the same way.
Some create penalties that can follow you for years. Others create taxes or higher premiums you may be able to fix. And some simply leave you paying for care you assumed was covered.
Part B timing. Your first window runs seven months: the three months before your 65th birthday month, that month, and the three after. If you're still working and covered by a current employer's plan, you can generally delay without penalty.
COBRA and retiree coverage don't count as current employer coverage. Otherwise, the penalty is 10% of the standard premium for each full 12 months you went without, and it usually lasts as long as you have Part B.
Drug coverage. Going 63 days or more in a row without Part D or other creditable drug coverage can add a penalty. It's 1% of the national base premium for each month without coverage, and it's added to your premium for as long as you have Part D. The base is $38.99 in 2026, and Medicare has set it at $41.33 for 2027.
HSAs. Once Medicare starts, you can't contribute to an HSA. If you sign up after 65, Part A can backdate up to six months, though not before the month you turned 65, so stop contributions ahead of time. Excess contributions face a 6% excise tax each year until corrected.
IRMAA. Medicare surcharges are based on your income from two years earlier, and a one-time spike like a large bonus or home sale can trigger them. If retirement or another life-changing event lowered your income, you can ask Social Security to use newer numbers with Form SSA-44.
Coverage gaps. Original Medicare generally doesn't cover routine dental, routine vision, most hearing aids, or long-term custodial care. Some Medicare Advantage plans add extra benefits, so compare what each option actually includes.
Which of these did you not know before?
P.S. Once a week, I email the best money article I read, with my take on this week's top Facebook posts and what's new on the Ways to Wealth blog. It's free, and you can sign up on the Ways to Wealth home page.
R.J. Weiss, CFP®
The content shared here is for educational and informational purposes only. It is not personalized investment, tax, legal, or financial advice. Consult a licensed professional before making decisions based on your specific situation.
