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The Medicare Enrollment Checklist

Seven questions to answer before you sign anything. Based on official CMS documents.

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1. Know your exact enrollment window dates. Your Initial Enrollment Period opens 3 months before the month you turn 65. Do not wait until your birthday. Verify your exact dates at Medicare.gov.
2. Confirm whether you’ll be automatically enrolled. Auto-enrollment only happens if you’re already receiving Social Security benefits. If not, you must apply at SSA.gov or by calling 1-800-772-1213.
3. If still working: verify your employer plan is qualifying coverage. The employer must have 20 or more employees. Get this confirmed in writing — “creditable coverage.”
4. Get the creditable drug coverage letter from your employer. This letter protects you from the Part D late enrollment penalty. Request it now. Keep it. Do not wait until retirement.
5. If you’re on COBRA — enroll in Part B during your IEP anyway. COBRA is not considered qualifying coverage by Medicare. The penalty clock starts if your enrollment window passes. You can have Medicare and COBRA simultaneously.
6. Compare plans with YOUR specific doctors, drugs, and zip code. Use the official Plan Finder at medicare.gov/plan-compare. Do not rely on general ratings — your network and formulary matter most.
7. Mark the Open Enrollment deadline in your calendar. October 15 – December 7 every year. Missing this window means waiting a full year to make changes.

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Get the printable PDF version

The PDF includes additional notes, source links (CMS.gov, Medicare.gov, SSA.gov) and the appeal process for each item. Enter your email and it will be delivered instantly.

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No spam. One email when new investigations publish. Unsubscribe anytime. Educational content only — not insurance advice. Source: CMS.gov · Medicare & You 2026 · SSA.gov