Medicare Enrollment Guide

Medicare Resources

Turning 65? Your Medicare checklist.

Medicare deadlines come with lifelong penalties if you miss them. Enter your birthday to see your dates, then check off each step from six months out through your first year.

Step 1 · Your birthday

Enter your date of birth to see your Medicare sign-up window, when coverage can start and your Medigap window.

Your progress

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We help marks the steps Security First can walk you through, at no cost.

Your birthday and checkmarks are saved only in this browser, so you can come back and pick up where you left off.

Avoid These

Four mistakes that cost people for years

Still working at 65?

Delaying Part B the wrong way

It’s only safe to delay when you have coverage from current work at a large enough employer. Retiree plans and COBRA don’t count, and the penalty lasts for life.

Have an HSA?

Contributing after Medicare starts

Money added once you have Medicare can mean a tax penalty. Backdated Part A coverage catches a lot of people who sign up late.

Take no prescriptions?

Skipping drug coverage

Going without Part D or other creditable coverage adds a penalty to your premium for as long as you have drug coverage later.

Happy with your plan now?

Missing the Medigap window

Your 6-month window is the easiest time to get any Medigap plan. After it, companies may ask health questions or turn you down.

Keep Your Progress

Want a copy in your inbox?

We’ll email you your dates and what’s left to do. No sales calls unless you ask for one.

More Medicare Resources

Guidance for your Medicare decisions.

Which plan pays what?

Medigap Chart

All 10 Medigap plans side by side, with 2026 costs.

Learn More →

Advantage or Medigap?

Medicare Options Compared

The two paths compared, plus a 30-second quick check.

Learn More →

Lost in the jargon?

Health Insurance Glossary

Deductibles, coinsurance and more, in plain English.

Learn More →

Turning 65 is easier with a guide.

We’ll walk you through enrollment, compare Medigap, Medicare Advantage and Part D plans for you and make sure no deadline slips by. In-person or virtual.

Prefer to call?
810-230-1266

Sources

General guidance, not legal or tax advice. Dates shown by the tool are estimates; Social Security confirms your enrollment dates. Security First Benefits is not connected with or endorsed by the U.S. government or the federal Medicare program.