The MedicarePROFESSOR
Lesson 3 of 5

Every Medicare enrollment window, one calendar.

Seven windows govern when you can enroll or switch, and two of them carry lifetime penalties for missing. Here is the whole calendar, in order, with the traps flagged.

1. Initial Enrollment Period (IEP)

Your personal seven-month launch window: the three months before your 65th birthday month, your birthday month, and the three months after. Enroll in the three months before your birthday month and coverage starts the first of your birthday month; enroll later in the window and the start date slips.

When you sign up (relative to 65th birthday month)When Part B starts
1 to 3 months beforeFirst day of your birthday month
During your birthday monthFirst of the following month
1 to 3 months afterFirst of the month after you enroll

2. Medigap Open Enrollment

Six months starting the month you are both 65+ and enrolled in Part B. Carriers must accept you with no health questions. This window does not repeat. If a Supplement is on your shortlist, this is when to buy it; details in the Medigap lesson.

3. Annual Enrollment Period (AEP): October 15 to December 7

The fall window everyone advertises. Anyone on Medicare can join, drop or switch Advantage and Part D plans, effective January 1. Plans re-file their networks, formularies and copays every year, so the plan you love can quietly change underneath you; your Annual Notice of Change letter, mailed in September, is the early warning.

4. Medicare Advantage Open Enrollment (MA-OEP): January 1 to March 31

A do-over window exclusively for people already on an Advantage plan: one switch to another Advantage plan, or back to Original Medicare plus a Part D plan. Medigap underwriting may still apply on the way back, which is why we treat this as a safety net, not a strategy.

5. General Enrollment Period (GEP): January 1 to March 31

The catch-up window for people who missed their IEP without other coverage. Coverage begins the month after you enroll, and the Part B late penalty usually rides along.

6. Special Enrollment Periods (SEPs)

Life events open personal windows: leaving employer coverage (8 months for Part B), moving out of a plan service area, qualifying for Extra Help or Medicaid, plan terminations and more. SEPs are the reason you should never assume you are stuck; ask before you resign yourself to a bad plan year.

The two penalties to respect

PenaltyHow it accruesHow long it lasts
Part B late penalty+10% of the Part B premium per full 12 months without coverage after eligibilityFor life
Part D late penalty+1% of the national base premium per month without creditable drug coverageFor life
Professor's note

Write two dates on the kitchen calendar: the first day of the month you turn 64 and 9 months (start planning), and October 15 every year after (re-shop). Every Medicare disaster story we have ever untangled began with a missed date.

Ask the professor

Lesson 3 questions

What happens if I miss my Initial Enrollment Period?

If you had no other creditable coverage, you wait for the General Enrollment Period, January 1 to March 31, with coverage starting the month after you enroll, and you may owe a permanent Part B late penalty of 10 percent for each full 12 months you delayed. The fix is expensive and lifelong, which is why we set calendar reminders for every client approaching 65.

I am still working at 65. Do these windows apply to me?

If your employer has 20 or more employees and you are actively covered, you can usually delay Part B penalty-free, then use an 8-month Special Enrollment Period when employment or coverage ends. COBRA and retiree coverage do not count as active employment, a trap that catches thousands of people every year.

What is the difference between AEP and the Advantage OEP?

AEP, October 15 to December 7, is for everyone: switch, add or drop Advantage and Part D plans for a January 1 start. The Advantage OEP, January 1 to March 31, is only for people already on an Advantage plan and allows one switch or a return to Original Medicare. Medigap purchases are governed by separate rules year-round.

Do Special Enrollment Periods really cover moving?

Yes. Moving out of your plan service area, losing employer coverage, moving into or out of a care facility, gaining Extra Help and several other events each open a window, usually two months, to change plans without waiting for fall. Tell us when life changes and we will tell you what it unlocks.

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