Your Medicare Checklist

Everything you need to do before your Medicare starts, in order. Use the date finder to see your personal deadlines, then book a call with us once you have your Medicare number.

Find your dates

Sign-up window opens
Sign up by (no gap)
Medicare starts
Sign-up window closes
Medigap open enrollment ends

Assumes you sign up for Part A and Part B when you turn 65. If you are still working and keeping employer coverage, see Working past 65 instead. Your date of birth stays in your browser; it is not sent anywhere.

Turning 65: your checklist

  1. 16 months before your 65th birthday

    Decide whether Medicare will be your main coverage

    • If you or your spouse are still working, ask HR: does the employer have 20 or more employees, and is the prescription coverage “creditable”? Their answers decide whether you can delay Part B (see Working past 65).
    • Contributing to an HSA? Stop contributions 6 months before you start Medicare, because Part A can be backdated up to 6 months.
    • On a Marketplace (ACA) plan? Plan to cancel it the day before Medicare starts. Premium tax credits end once you qualify for premium-free Part A.
  2. 23 months before your birthday month

    Sign up for Part A and Part B

    • Apply online at ssa.gov/medicare/sign-up, or call Social Security at 1-800-772-1213 (TTY 1-800-325-0778).
    • Already collecting Social Security? You are enrolled automatically. Your red, white and blue card arrives about 3 months before your birthday month, so there is nothing to file.
    • Sign up before your birthday month and coverage starts on the 1st of that month with no gap.
  3. 3As soon as your Medicare card arrives

    Book your plan review with us

    • Your card shows your Medicare number and Part A and Part B start dates. We need both to enroll you.
    • On the call we compare Medicare Supplement (Medigap) plans, Medicare Advantage plans and Part D drug plans for your doctors, prescriptions and budget. There is no cost for our help.
    • Pick a time online or call 312-800-0751.
  4. 4Before your Medicare start date

    Enroll in your plan and close out old coverage

    • We submit your Medigap, Medicare Advantage or Part D application so it starts the same day as Part B.
    • Cancel employer, COBRA or Marketplace coverage only after your new plan is confirmed, effective the day before Medicare begins.
  5. 5Every year, October 15 to December 7

    Annual review

    • Drug plans and Medicare Advantage plans change their prices and drug lists every January. We review your plan each fall and let you know if a switch saves you money.

Working past 65 or covered by a spouse’s employer plan

Employer has 20 or more employees

The employer plan pays first, so you can delay Part B without a penalty. Many people still take premium-free Part A at 65, unless they want to keep contributing to an HSA.

Employer has fewer than 20 employees

Medicare pays first. Sign up for Part A and Part B at 65 even if you keep the employer plan, or claims may not be paid.

When you retire or the employer coverage ends

  • You have 8 months to sign up for Part B with no penalty. Apply 1 to 2 months before your last day of coverage so there is no gap.
  • Apply online at ssa.gov/medicare/sign-up/part-b-only with two forms: the CMS-40B (Part B application) and the CMS-L564 (your employer completes this to confirm your coverage).
  • Join a Part D or Medicare Advantage plan within 63 days of losing employer drug coverage.
COBRA and retiree plans do not count. They do not let you delay Part B. If your only coverage after 65 is COBRA or a retiree plan, sign up for Part B to avoid a lifetime penalty.

Deadlines that cost money if you miss them

WhatDeadlineIf you miss it
Part BYour 7-month sign-up window around 65, or 8 months after employer coverage endsPremium goes up 10% for each full year you went without it, for life. Next chance to enroll is January to March, with coverage starting the next month.
Part D (drug coverage)When you first get Medicare, or within 63 days of losing creditable drug coverageAbout 1% of the national base premium for every month without coverage, for life.
Medigap open enrollment6 months starting the month your Part B begins (age 65 or older)Insurers may ask health questions and can decline you or charge more. Some states give extra rights.

Have these ready for our call

  • Your Medicare card (or Medicare number and Part A and Part B start dates)
  • A list of your doctors and specialists
  • Your prescriptions with dosage and how often you take them
  • Your preferred pharmacy
  • The end date of your current coverage
  • Any questions from your HR department or spouse

Questions? Talk to a licensed agent.

We will walk you through every step and help you choose a plan. There is no cost for our help.

Official sources: When can I sign up? and When does coverage start? on Medicare.gov; current Medicare costs.

We do not offer every plan available in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) for information on all of your options. Independent Health Agents is not connected with or endorsed by the U.S. government or the federal Medicare program.

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