The Turning-65 Medicare Checklist: A Step-by-Step Guide to Secure Your Coverage

As Medicare Open Enrollment gets closer each year, there is a barrage of Medicare marketing by mail, on TV, and on the radio. If you’re just turning 65 and moving from an employer’s plan to Medicare, it can be especially daunting having so many options to choose from and such a different type of coverage. But taking a little time to understand Medicare and the types of plans that are offered can go a long way toward giving you peace of mind.

For most retirees, Original Medicare paired with a Medigap policy (like the gold-standard Plan G) provides both predictable out-of-pocket costs and comprehensive healthcare coverage. Read on to find out what you need to know to enroll smoothly in Medicare at 65.

Medicare Enrollment timeline

The first chance most people have to sign up for Medicare is when they turn 65 (unless you have a special circumstance like having end-stage renal disease or ALS). Your initial enrollment period lasts three months before the month you turn 65, your birthday month, and three months after. During this time, you can enroll in Original Medicare and the Part D prescription drug plan.

Your eight-step Medicare enrollment checklist

• Step 1: Calculate your Initial Enrollment Period (IEP). Identify your seven-month window when you can enroll in Medicare. It begins 3 months before your birthday month, includes your birth month, and ends three months after your birthday month (for a total of 7 months).
• Step 2: Decide whether to delay Part B. If you turn 65 and are still employed, you may be able to stay on your employer’s health plan. Your employer is required to notify you if their coverage qualifies as “creditable.” If it doesn’t, you’ll need to enroll in Medicare to avoid late-enrollment penalties later.
• Step 3: Create your My Social Security account. If you already receive Social Security benefits, you’ll be ready to enroll in Medicare – in fact, the Social Security Administration will automatically enroll you in Original Medicare unless you choose another plan. If you aren’t getting Social Security yet, and don’t already have an online account, you’ll need to set one up by visiting SSA.gov.
• Step 4: Enroll in Original Medicare. Original Medicare is comprised of different types of coverage. Part A, which pays for hospital care and Part B, which pays for doctor visits and other outpatient care. You can begin the signup process for Original Medicare on the Social Security Administration’s website. Medicare Part D, Part C or Medicare Advantage and Medicare Supplement are considered private Medicare plans created to fill in the gaps of coverage not covered by Original Medicare.
• Step 5: Compare your supplemental options. Many people over 65 want more coverage than what Original Medicare supplies. Supplemental plans like Medigap or Medicare Advantage help pay for Medicare copays and other out-of-pocket expenses you’re left with when you just have Original Medicare. Medigap plans, specifically, provide comprehensive health coverage and no restrictions on your healthcare providers. And some plans, like Plan G, cover nearly all your expenses, making it a good choice for new enrollees who want a predictable healthcare budget.
• Step 6: Secure your Medigap policy during your Open Enrollment Period. Once you have enrolled in Medicare Part A and Part B, you can sign up for a Medicare Supplement plan. You need to make sure you enroll during your Medigap Open Enrollment Period, so you have what is known as guaranteed issue. This means you can sign up for a plan and don’t have to undergo medical underwriting – meaning the carrier can’t deny you a plan because of your health status. Your Medigap Open Enrollment lasts for six months, beginning the first day of the month you are both 65 and enrolled in Part B.
• Step 7: Choose a standalone Part D prescription drug plan. When you choose a Medigap plan, you’ll also need to pick a Part D prescription drug plan. You must have a Part D plan, or you could have a monthly fee added to your Medicare premiums. You can compare Part D plans on our sister site SmartMatch’s Medicare’s plan compare site.
• Step 8: Set up premium payments and finalize coverage. You can pay for your Medicare Part B plan by having it automatically deducted from your Social Security benefits. If you don’t get Social Security, you can pay for your Part B bill (which you’ll receive every three months):
  • Through your online Medicare account,
  • By setting up recurring payments via Medicare Easy Pay,
  • Directly from your bank account via a draft,
  • By sending a check in the mail.

Note: Your Medigap premiums can be paid through your Social Security benefits (if your insurance company allows this) or directly through your carrier. After you’ve enrolled in a plan, contact your carrier to find out how to pay your monthly premiums. Most insurers accept bank drafts, debit or credit cards, and checks.

What documents do I need for Medicare?

When you’re preparing to enroll in Medicare, it’s best to have the documentation you need on hand. It will speed up the process and make it go more smoothly. Documents needed for Medicare enrollment, and information to have at the ready, include:

• Your Social Security card.
• Birth certificate to prove your age.
• Proof of citizenship, like a passport or green card, if you weren’t born in the United States.
• Information on your military service (like discharge papers), if you served.
• W-2 forms or tax returns to prove recent work status and determine if you qualify for an income-related monthly adjustment amount (IRMAA). This only applies to high-income earners.
• Health insurance information, including start and end dates of your current, or last, group health plan.
• A valid email address and mailing address.

You’ll also want to have a list of your doctors, preferred pharmacy, and the medications you take before enrolling in a plan. This will help you choose a plan that includes your preferred providers and covers as many of your prescription drugs as possible.

Should I choose Medicare Advantage or Medigap at 65?

Original Medicare (Part A and Part B) and a Part D drug plan cover hospitalizations, doctor’s visits, and prescription drugs only. But you will have to pay copays, coinsurance, and deductibles on these services. Medicare Advantage and Medigap plans are more comprehensive coverage that lower your out-of-pocket costs, which is especially beneficial if you have one or more chronic health conditions. There are pros and cons to both kinds of plans, so make sure to talk with a trusted agent like those from United Medicare Advisors before making your choice.

Medicare Advantage

• Pros: Low monthly premiums.
• Cons: Has provider networks that may not include your doctor. May require prior authorization for some treatments. Can come with higher copays and coinsurance. Out-of-pocket maximums change annually.

Medigap

• Pros: Accepted by all doctors that take Medicare assignment. Allows you to travel around the country and be covered. Reduces unexpected out-of-pocket costs, especially Medigap Plan G or Plan N, which cover 100% of the gaps left by Part A and B after you meet your annual Part B deductible.
• Cons: Higher monthly premiums.

What happens if I miss my Medicare enrollment window?

It’s vital that you enroll in Medicare during your Initial Enrollment Period (unless you have creditable coverage through an employer) to avoid late penalties. Most people don’t receive a Part A penalty, but you’ll have to pay Part B and Part D late enrollment penalties for the rest of the time you are enrolled in Medicare.

If you miss your enrollment window, you’ll have to pay:

• Medicare Part B penalty is 10% of the standard premium (anticipated to be $221 in 2027) for each 12-month period you should have had Part B coverage.
• Medicare Part D penalty is 1% of the national base beneficiary premium ($41.33 in 2027) for each month you should have had Part D coverage but didn’t.

Why expert guidance beats doing it yourself

You can enroll in Medicare during your Initial Enrollment Period on your own. It’s wiser, however, to work with a guide. There are so many plan options, sorting through them can take hours of research — and that’s if you have trusted resources at your disposal. The plan you choose will have such a major impact on your health and budget that choosing a trusted, licensed advisor should be a key component of your enrollment decisionmaking.

A checklist is a great tool to have when enrolling in Medicare at 65. But doing so is a complicated process. Getting additional help can make it go more smoothly and ensure you have the policy you need at a price you can afford. Talk with a licensed United Medicare Advisors agent and consider a Medigap Plan G policy during your open enrollment window.