Pearl Insurance Services

Tool · Medicare Timeline

When do you need to do what?

Medicare has windows that open and close on a schedule. Your timeline depends on a few things — work coverage, Social Security, HSA. Tell us yours and we'll branch the calendar accordingly.

About you

Already receiving Social Security?
Still working at 65?
Have insurance through that employer?
Contributing to an HSA?

Heads up

✨ Because your birthday falls on the 1st of the month, Medicare counts you as turning 65 on the last day of the prior month. Your timeline has been adjusted one month earlier than most people’s.

  1. May 2027

    Your Initial Enrollment Period opens

    A 7-month window: the 3 months before your birth month, your birth month, and the 3 months after. Enrolling in the first 3 months gets you coverage the fastest.

  2. August 2027

    Turn 65 — Medicare eligible

    You must actively enroll through Social Security (online, by phone, or in person). Part A is free for most people; Part B has a monthly premium.

  3. August 2027

    Medigap Open Enrollment begins (6 months)

    Starting the month your Part B is effective, you have a 6-month one-time window to buy any Medigap policy with guaranteed acceptance — no health questions. After this window, insurers in most states can deny you or charge more.

  4. October 2027

    Annual Election Period (Oct 15 – Dec 7)

    Every year, this is when you can switch Medicare Advantage plans, join or drop a Part D plan, and make changes effective January 1.

  5. November 2027

    Initial Enrollment Period closes

    Miss this window without other creditable coverage and you'll face a Part B late enrollment penalty of 10% per full year late — for life.

Timeline based on the rules in effect today. Individual situations can shift dates — when in doubt, confirm before assuming.

Want Adam to review this with you?

Your results are yours — no form required.

If you’d like help applying this to your actual doctors, prescriptions, ZIP code, budget, and timing, you can book a 30-minute review with Adam at Pearl Insurance Services.

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