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Turning 65? Your Medicare Guide Starts Here.

Your Initial Enrollment Period is a 7-month window around your 65th birthday. Use it on purpose — not in a rush.

The enrollment window

IEP typically starts 3 months before your 65th birthday month and lasts 7 months total. Signing up earlier in the window can help coverage start when you want it to. Waiting until after the window can create gaps or penalties unless an exception applies.

If you have employer coverage

If you or a spouse is still working at a company with 20 or more employees, you may be able to delay Part B without a late penalty. Get written confirmation that the coverage is creditable. HSA contributions generally must stop once you enroll in Medicare.

Decisions after Parts A and B

Once Original Medicare is in place — or you have chosen Medicare Advantage — you still need a plan for prescriptions and for the remaining medical costs. That is the Advantage vs. Supplement decision, plus Part D.

Common mistakes at 65

Missing IEP, assuming a Marketplace plan can continue unchanged, delaying Part B without a valid reason, forgetting Part D, and choosing a plan because a friend likes it are all avoidable. Your doctors, drugs, and travel habits are the better starting point.

Want the full story? Get my book. Medicare 2026: Choose the Right Plan & Avoid Costly Mistakes walks through how Medicare is built. It does not pick a plan.

For the other pages on this topic, open the Medicare at 65 guide.

2026 figures

Medicare eligibility date

See when Part A and Part B can start at 65, and your Initial Enrollment window.

Read: Turning 65? Your Medicare timeline

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Worksheet

Still working at 65?

A sketch of delaying Part B with employer coverage, HSAs, and the clock after coverage ends.

Read: Do I need Medicare at 65 if I’m still working?

Does the employer have 20 or more employees?
Whose job is the coverage from?
  • Ask the benefits office how many employees the group has, in writing. Size decides whether you can delay Part B.
  • HSA contributions generally must stop once you enroll in Medicare Part A. Timing Part A with an HSA is worth a Social Security conversation.
  • After qualifying coverage ends, a Part B Special Enrollment Period typically lasts eight months. Do not wait for fall Annual Enrollment to sign up for Part B.
  • Part D has its own creditable-coverage rules (including a 63-day gap). Ask whether the drug coverage is creditable.
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Worksheet

HSA stop date when Part A starts

The last month you can contribute to an HSA is the month before Medicare Part A starts.

Read: HSAs and Medicare Part A

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Worksheet

COBRA vs Medicare at 65

COBRA is not the same as current employer coverage. Delaying Part B for COBRA can mean a penalty.

Read: COBRA vs Medicare at 65

Where are you?

COBRA is continuation coverage after a job ends. It is not the same as current employer coverage. It generally does not let you delay Part B without a late-enrollment penalty. If you are turning 65, enroll in Part B on time unless you still have coverage from a current employer with 20 or more employees.

If you have both Medicare and COBRA, Medicare pays first on covered services. This is not a determination. Ask the COBRA administrator and Social Security.

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