Turning 65 — Your Tech + Benefits Checklist

The 7-month window (and beyond)

Medicare calls this your Initial Enrollment Period. It starts 3 months before your birthday month, includes the birthday month itself, and ends 3 months after. Missing it can mean lifetime late penalties — so the earlier you start, the better.

1. 7 months before 65

   Initial Enrollment Period opens

   Your 7-month Medicare sign-up window begins 3 months before the month you turn 65. Start by logging in at ssa.gov to see your benefit estimate and confirm your records are correct.

2. 6 months before 65

   Decide your Medicare path

   Choose between Original Medicare (Parts A + B, often paired with Medigap and Part D) or Medicare Advantage (Part C). A SHIP counselor in your state gives free, unbiased help — no sales pitch.

3. 3 months before 65

   Enroll in Medicare

   Apply at medicare.gov or by calling Social Security at 1-800-772-1213. If you already get Social Security benefits, enrollment in Parts A and B happens automatically.

4. 2 months before 65

   Coordinate with employer coverage

   If you are still working with group coverage, talk with HR about whether to delay Part B. If you leave the job, you get a Special Enrollment Period — COBRA does not count as creditable coverage in most cases.

5. The month you turn 65

   Coverage begins

   Medicare coverage starts on the first day of your birthday month (or the month before, if your birthday is on the 1st). Watch the mail for your red-white-and-blue Medicare card.

6. 1 month after

   Set up your MyMedicare account

   Go to mymedicare.gov and create an account. This is where you track claims, find in-network providers, and compare plans during Open Enrollment.

7. 3 months after

   Review prescription coverage

   Medicare Annual Enrollment runs October 15 through December 7. Use Plan Finder on medicare.gov to compare Part D drug plans with your actual prescriptions entered.

8. 1 year and ongoing

   Annual Medicare review

   Each fall, double-check your plan still covers your doctors, pharmacies, and medications. Plans change their drug lists and provider networks every year.