Medicare · June 27, 2026 · 2 min read
Three Medicare mistakes that cost real money
The penalties are permanent, the windows are short, and almost nobody tells you the rules ahead of time. Here are the three that catch people most often.
Medicare is not complicated because the coverage is complicated. It is complicated because the calendar is complicated. Nearly every expensive Medicare mistake is a timing mistake.
Mistake one: missing the initial enrollment window
Your Initial Enrollment Period runs seven months around your 65th birthday — the three months before, your birthday month, and the three months after.
Miss it without other qualifying coverage and Part B costs 10% more, permanently, for every full year you went without. That penalty does not expire. It follows the premium for life.
Mistake two: assuming employer coverage always protects you
Working past 65 with employer coverage can legitimately delay enrollment without penalty — but only if the employer is large enough and the coverage qualifies. Retiree coverage and COBRA generally do not count.
- Confirm in writing that your plan is creditable coverage before you decline Part B
- Ask your HR department for the specific letter — they know the one
- If you are on a small-employer plan, assume you need to enroll on time
Mistake three: skipping Part D because you take no medications
This is the one that stings most, because the logic feels sound. No prescriptions, no drug plan, no cost.
Except the Part D late-enrollment penalty accrues for every month you go without creditable drug coverage, and you pay it once you finally enroll — which nearly everyone eventually does.
A drug plan you barely use is inexpensive. A lifetime penalty on the plan you eventually need is not.
The window that opens exactly once
One more, since it is the least known: your Medigap guaranteed-issue window opens for six months after Part B begins. Inside it, you can buy any supplement regardless of health. Outside it, insurers in most states can decline you or price you on your medical history.
If you are approaching 65, put a reminder on your calendar four months before your birthday and call us. There is no charge for the conversation, and the timing is the whole game.
This article is educational and is not individualized financial, tax, or legal advice. Please speak with a licensed professional about your own situation.
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