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Medicare Enrollment Timeline: What to Do Before You Turn 65

The seven-month Initial Enrollment Period, working-past-65 rules, and the deadlines that cause the most penalties.

7 min readUpdated March 5, 2026Zaki Enterprise Advisors

Miss a Medicare deadline and you can face lifetime late-enrollment penalties. Use this timeline to enroll in the right window.

Initial Enrollment Period (IEP)

Starts three months before your 65th birthday, includes your birthday month, and ends three months after.

Working past 65

If you have credible coverage through a large employer, you can delay Part B without penalty. Get a written credible-coverage letter from HR.

Special Enrollment Periods

Losing employer coverage or moving out of a plan's service area opens an SEP — usually 63 days from the qualifying event.

Annual Enrollment (Oct 15 – Dec 7)

Every year you can switch Advantage plans or drug plans. Even if you love your plan, review the drug formulary — it changes yearly.

About the author

Written by Zaki Enterprise Advisors — Licensed Insurance & Tax Professionals.

Reviewed by the same Texas advisors who work with our clients on tax preparation, ACA, Medicare, and property & casualty coverage.

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