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The Turning-65 Checklist
The short answer: start about six months before your 65th birthday: confirm in writing whether your employer coverage is creditable, mark your seven-month enrollment window, and enroll in the three months before your birthday month so coverage starts on time. The checklist below walks it step by step.
Print this, stick it on the fridge, and check things off as you go. It covers the windows that matter and the mistakes that cost people — in plain language, with no numbers to memorize.
The timeline at a glance
| When | What to do |
|---|---|
| 6–12 months before 65 | Mark your seven-month enrollment window; ask HR in writing whether your coverage is creditable; list your doctors and prescriptions |
| 3–4 months before | Enroll, or confirm your automatic enrollment; plan your last HSA contribution if you have one |
| During your window | Decide on drug coverage and how you’ll cover Medicare’s gaps; enrolling in the three months before your birthday month starts coverage on time |
| Birthday month and after | Verify the cards arrived and coverage actually started; put a yearly coverage review on the calendar |
6 to 12 months before your 65th birthday
- Mark your Initial Enrollment Period. It runs seven months: the three months before your birthday month, your birthday month, and the three months after.
- If you’re still working: ask HR whether your employer coverage is creditable — this one answer decides whether you can delay without penalties. Get it in writing.
- List your doctors and prescriptions. This list — not the premium — is what actually determines which coverage fits you.
- Check your Social Security status. If you’re already drawing benefits, Parts A and B enrollment is automatic. If not, you’ll need to enroll yourself.
3 to 4 months before
- Start comparing your two routes: Original Medicare with a Supplement and drug plan, or a Medicare Advantage plan. Neither is right for everybody.
- Read the 2026 Medicare Roadmap — the plain-language walkthrough of how the parts fit together.
- Talk it through with someone — a friend who’s been through it, or an independent agent. There’s no cost either way, and a second set of eyes catches things.
During your enrollment window
- Enroll early in the window — enrolling in the three months before your birthday month generally means coverage starts without a gap.
- Don’t skip drug coverage because you take nothing today. The Part D late penalty is small monthly but permanent — it follows you for as long as you have drug coverage.
- Confirm your doctors and prescriptions are covered under whichever plan you choose — before you sign, not after.
- Keep every confirmation letter. A folder for Medicare mail saves real headaches later.
After you’re enrolled
- Watch for your Medicare card and check the effective dates.
- Recheck your coverage every fall. Open Enrollment (October 15 – December 7) is when you can change plans for the next year — plans change what they cover, even if you don’t.
- Ask questions when letters arrive. If something doesn’t make sense, it’s worth a phone call before it becomes a problem.
Want a hand with any of it?
Call or text 770-765-7007 — plain-language answers at no cost, and someone who’s still there after you’re enrolled. Or start with the Medicare basics.