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Medicare Enrollment Basics: Parts A, B, C, and D

Medicare & HealthcareUpdated 2025-06-05

Medicare enrollment looks simple — you turn 65 and sign up. The reality is a labyrinth of four "Parts," a seven-month enrollment window, and late-enrollment penalties that follow you for the rest of your life. Getting the mechanic right at 65 saves you thousands of dollars over the next 20 years.

The four parts

The Initial Enrollment Period (IEP)

The IEP is a 7-month window: the three months before your 65th birthday month, your birthday month, and the three months after. Enroll during this window and coverage starts the month you turn 65 (or the following month if you enroll in the back-half months). Miss it and you face the General Enrollment Period (January 1–March 31 each year, coverage starting the following month) plus permanent late penalties.

The late-enrollment penalties

Working past 65 — the employer-coverage exception

If you are still working at 65 and covered by an employer group health plan from a company with 20 or more employees, you may delay Part B without penalty. When you eventually leave that coverage, you get an 8-month Special Enrollment Period (SEP) under §1837(i) to enroll in Part B without penalty. The SEP starts the month after employment or coverage ends, whichever comes first.

The 20-employee threshold matters: at a smaller employer, Medicare becomes the primary payer at 65 and the group plan becomes secondary. Failing to enroll in Part B leaves you effectively uninsured for the share Medicare would have paid. Confirm with HR whether your employer is "large" or "small" for Medicare secondary-payer purposes.

COBRA and retiree coverage do not count

COBRA and most retiree health plans are not "creditable coverage" for the Part B SEP. Relying on COBRA past 65 and delaying Part B triggers the lifetime penalty when you finally enroll. The federal rule is clear, and the mistake is common.

Social Security and Medicare

If you start Social Security before 65, you are automatically enrolled in Parts A and B at 65 (you can decline B if you have qualifying employer coverage). If you have not yet started Social Security, you must actively enroll in Medicare via the SSA — visit ssa.gov, call SSA, or go to a Social Security office.

Common mistakes

Sources

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