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Preparing for Medicare Worksheet

Using this worksheet may help you or a SHIBA counselor understand your Medicare options and deadlines. Get a printable PDF of this worksheet.

1. Know your Medicare choices

If you are still working, ask your employer:

  • Should I enroll in Part A hospital coverage (no monthly premium to most people) and keep my group health insurance? Yes No

  • Do I need to enroll in Medicare Part B (doctor/outpatient coverage with a monthly premium)? Yes No

  • Does my insurance offer “creditable coverage” for Medicare Part D (prescription drug insurance)? Yes No
    (If no, you may need to enroll in Medicare Part D)

  • When I retire, do I have any retiree health insurance benefits? Yes No

Do you have medical insurance through a spouse?

  • Does your employed spouse have employer benefits? Yes No

  • Is he or she working (not on COBRA or retiree coverage)? Yes No

  • Are you eligible for health benefits through your spouse’s employer? (When you ask the employer, be clear that you are Medicare eligible.) Yes No
    If “yes,” you may be able to decline Medicare Part B but ask the employer about this.

Are you a government employee/veteran? 

Ask your benefit specialist how government insurance works with Medicare – as an employee or as a retiree. 

2. Will your Medicare card arrive automatically?

Are you now collecting Social Security early retirement benefits? 

  • If yes, you should be automatically enrolled in Medicare Part A and Part B. Your Medicare card will arrive about three months before you turn 65. You must decide whether to keep or decline Part B.
    If you do not automatically receive your card, contact your local Social Security office.

Retired early but delaying Social Security until full retirement age?

  • If no, contact Social Security up to three months before you turn 65, or within three months after, to enroll in Medicare. Contact Social Security for Part B premium payment options/questions.

3. Chart your deadlines

  • I start Medicare: On the first of the month you turn 65 (or one month earlier if your birthday is on the first day of the month.)

  • 7-month Initial Enrollment Period (applies to Parts A, B, C, and D):

    • Starts (3 months before your birthday month) __________________ .

    • Ends (3 months after your birthday month) ___________________ .

  • Disability initial enrollment period
    • Starts (Parts A & B automatically start in 25th month; Parts C & D, 21st month of disability) __________________ .
    • Ends (Parts C & D, 27th month of disability) __________________ .
  • Insurance companies must accept my application for a Medigap plan:
    • Starts (date your Part B starts) __________________ .
    • Ends (6 months later) ___________________ .

4. Consider additional plans to your Medicare

Original Medicare consists of Parts A and B (hospital/doctor coverage). People with only this coverage don’t have prescription drug coverage unless they enroll in a plan. They pay deductibles, 20 percent of doctor bills and other costs. Many people add coverage with one of the following options:

  • Original Medicare (Parts A and B) can go along with:

    • a Medigap (also called a supplement) and

    • a Part D plan (prescription drug coverage)

  • Medicare Advantage (This is Part C), bundles Parts A and B and often includes drug coverage

Other coverage, from VA, Tricare, Medicaid, or an employee/retiree program, may also be available to you.

If you want Rx coverage:

  • Medicare Advantage plan: Drug coverage is usually integrated in your plan. You won’t choose separate drug coverage. (Exception: Private Fee-For-Service plan members can choose separate Rx plans.) Be sure you know if it is included.

  • Original Medicare (Parts A and B): You must select and enroll in a drug plan. Visit Plan Finder. Find tips for using this plan finder here: Part D Step by Step.

  • VA, Tricare, or employer Rx coverage: If this is available to you, contact them to see if the coverage meets your needs.

5. Do I qualify for help with Part D costs?

  • Is your annual monthly income less than $1,615 (2020) for a single person or $2,175 (2020) for a married couple living together? Yes No

  • Are your resources less than $14,610 (2020) for a single person or $29,160 (2020) for a couple? (bank accounts, investments, and IRAs count, but don't count a home or car) Yes No

You may review eligibility and apply for assistance through Social Security. SHIBA is also happy to help you with this application.

6. Ask your doctor’s billing office what insurance it takes.

"Do you accept and bill Medicare?" (also known as Original Medicare or Fee-For-Service Medicare.) "Private Fee-for-Service" is a type of Medicare Advantage plan. Yes No

List the Medicare Advantage plans your doctor will bill; is she/he “in network”?
__________________________________________________________ __________________________________________________________ __________________________________________________________
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7. Select your Medicare insurance

In most areas, there are multiple Medicare supplements, multiple Medicare drug plans and multiple Medicare Advantage plans. Ways to review plans:

  • Oregon publishes a Guide to the Medicare plans available in Oregon.

  • A SHIBA counselor can explain your choices: 800-722-4134 (toll-free)

  • Visit to compare drug, health, and Medigap plans.


  • Get your Medicare enrollment information from the source that protects you!

    • Part A or Part B Questions: Social Security – Document it!

    • Part C (Medicare Advantage) or Part D (Rx): Medicare – Document it!

  • If you delay Part B enrollment because of other coverage, confirm your decision with Social Security to avoid a late enrollment penalty.
  • Keep a log (spiral notebook works)
    • Document phone calls: include names of people you speak with, dates, and times