Medicare Enrollment & Deadlines – When and How to Enroll

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Turning 65: Initial Enrollment Period

If you’re already receiving Social Security, you may be auto-enrolled. If not, you’ll apply through the Social Security Administration. You can delay Part B when covered by qualifying employer insurance—but rules matter. We’ll help you determine whether delaying Part B makes sense and how to document employer coverage correctly.

Medicare Enrollment Periods 101

Know the key windows:

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Initial Enrollment Period (IEP)

A 7-month window around your 65th birthday.

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Annual Enrollment Period (AEP) 

Oct 15–Dec 7 each year to review Advantage and Part D plans.

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Medicare Advantage Open Enrollment

Jan 1–Mar 31 to make a one-time change if already in an MA plan.

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Special Enrollment Periods (SEP)

Triggered by qualifying events like retiring from employer coverage or moving.

Realegacy Partners keeps you on schedule so you don’t miss time-sensitive opportunities.

Annual Enrollment Period (AEP)

Each fall, you can review or change your Medicare Advantage or Part D plan for the next year. Plans and costs change—AEP is the ideal time for a checkup with Realegacy Partners.

Special Enrollment Periods

Common SEPs include: leaving employer coverage after 65 (generally an 8-month window for Part B), moving out of your plan’s service area, or losing creditable drug coverage. We’ll help document your situation and choose next steps promptly.

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Avoiding Late Enrollment Penalties

  • Part B – A 10% premium increase for each full 12-month period you delayed without creditable coverage.
  • Part D – Roughly 1% of the national base premium per month without creditable drug coverage.

Realegacy Partners helps you plan ahead so deadlines don’t become costly surprises.

FAQs on Medicare Enrollment

  • Is enrollment automatic at 65?

    Only if you’re already receiving Social Security.

  • What if I’m still working?

    Employer size matters; large employers often allow a Part B delay without penalty.

  • What documents do I need?

    Your SSA info; if delaying Part B, employer verification forms.

  • Can I change plans later?

    Yes—AEP (and MA OEP for Advantage) allow changes; Medigap switches may require underwriting outside protected windows.

How to Enroll in Medicare

Apply online via Social Security, by phone, or at your local SSA office. For Medicare Advantage or Part D, you’ll choose a private plan during the appropriate window. Need a hand getting started? Contact us and we’ll map out the steps.