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An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

Medicare

How to enroll in Medicare: A simple step by step sign up guide to walk you through it

By
Erin Prater
Erin Prater
Down Arrow Button Icon
By
Erin Prater
Erin Prater
Down Arrow Button Icon
October 26, 2023, 5:00 AM ET

You just turned 65 and are eligible for Medicare. Congrats! And also, apologies, because the process of applying can be a beast—seemingly so, anyway.

It really shouldn’t be, because you’ve got things to do. Perhaps you’re still working, or enjoying retirement. Spending time with the grandkids or taking up a new hobby.

To help, we’ve created a visual guide to applying that should make the process simpler.  But first, answers to a few questions you might have.

What is Medicare?

Medicare is a federal health insurance program for legal citizens 65 and older, or younger people who have disabilities and/or end-stage renal disease.

Will I automatically be enrolled for Medicare when I turn 65?

It depends, according to Medicare. If you applied for retirement benefits from Social Security or the Railroad Retirement Board at least four months before you turn 65, you’ll automatically be enrolled in Part A and Part B on your 65th birthday.

If you haven’t applied for retirement benefits yet, you’ll need to sign up for Medicare when you turn 65. However, if you have health insurance through an employer, you may want to wait to sign up or just elect one part. In some instances, even if you and/or your spouse are still working and have private insurance, you may be required to sign up for Part B. Be sure to talk to your company’s benefits department for more details.

When should I apply for Medicare?

You may enroll in Medicare as early as three months before your 65th birthday month, during your 65th birthday month, and as late as three months after your 65th birthday month, for a total of a seven-month enrollment window, referred to as your initial enrollment period. For instance, if your 65th birthday is Jan. 1, 2024, you can apply for Medicare as early as Oct. 1, 2023, and as late as April 30, 2024.

Additionally, there’s a general enrollment period that runs from Jan. 1-March 31 each year. If you’ve missed out on your initial enrollment period and don’t have a special enrollment period, you’ll need to wait for another general enrollment period to apply.  Note that there may be a lifetime penalty if you’re applying further out than three months after your 65th birthday, assessed in the form of indefinite higher premiums.

The annual open enrollment period Oct. 15 through Dec. 7 gives those already enrolled the chance to drop coverage or change their Medicare plan effective Jan. 1.

What is a special enrollment period?

If you missed your initial enrollment period, you may be allowed to enroll penalty-free during a special enrollment period. These usually last six months and may last as long as a year. Special circumstances include:

  • experiencing a natural disaster or emergency during your initial enrollment period
  • receiving inaccurate or misleading information from your health plan or employer
  • being imprisoned during your initial enrollment period
  • losing health insurance coverage from your job or your spouse’s
  • volunteering or serving in a foreign country during your initial enrollment period

When does my Medicare coverage start?

If you apply during that three-month window before your birthday month, your coverage will start on the first day of your birthday month. For instance, if your birthday is July 31 and you applied June 1, your coverage will start July 1.

If you apply during your birthday month or during the three-month window after, your coverage will start on the first of the month following the month you applied. For instance, if your birthday is July 31 and you apply Oct. 28, your coverage will start Nov. 1.

What is the difference between Medicare Part A and Part B?

Part A helps pay for hospitalizations, nursing home care, and home health care. Most people don’t pay a premium for Part A, if they or their spouse paid Medicare taxes while working at some point. 

Those who don’t qualify for premium-free Part A can buy in for a fee. In 2023, it was $506 per month for those who paid Medicare taxes for less than 30 quarters, and $278 per month for those who paid Medicare taxes for 30-39 quarters.

Part B helps cover services from doctors and other medical professionals, outpatient care, home health care, durable medical equipment like wheelchairs and walkers, and preventative services like screenings, shots, vaccines, and “well visits.” 

Everyone pays a premium for Part B, which may be adjusted down based on your income. In 2023, it was $164.90 per month, but higher for those who make over $97,000 a year if they’re single, or $194,000 a year jointly if they’re married. There are also savings programs to help lower-income individuals afford premiums.

Will I pay anything aside from potential premiums?

Yes. You’ll pay a 20% coinsurance on Part A after a $1,600 deductible, meaning that you’ll pay 20% of the negotiated cost of whatever services were provided. There are additional costs you might encounter, like a daily coinsurance of $400 on the 61st-90th days of hospitalization. With Part B, you’ll pay 20% of costs after a $226 deductible.

Is this test, item, or service covered?

You can search and find out here, on the Medicare website.

What isn’t covered by Medicare?

Some Medicare plans offered by privately run companies, like Medicare Advantage or Medicare Cost plans, cover some services that original Medicare doesn’t. But, in general, the following are not covered:

  • Long-term care
  • Most dental care
  • Eye exams performed so you can get prescription glasses
  • Cosmetic surgery
  • Dentures
  • Massage therapy
  • Routine physical exams
  • Hearing aids and exams for fitting them
  • Concierge care (retainer-based care)

How do I know which one I should sign up for, or if I should sign up for both?

The right answer varies depending on your situation, and looks different based on factors like whether or not you or your spouse are still employed and, if so, whether or not the employer has 20 or more employees.

Medicare has an explainer on what to do in various situations, including if you’re still employed, if you’re on insurance bought off the marketplace, Medicaid, or COBRA. You can find that here. It’s a part of a larger website that helps guide you through the Medicare decision-making process. You can find that site here.

A step-by-step guide through the online enrollment process

1. Register for an account. It may seem counter-intuitive, but to sign up for Medicare, you’ll need to go to the Social Security Administration website. Use this link to get there. Under “Sign up for Medicare,” click the “Apply online” button, then accept the terms of service and click “Next.”

2. Apply for benefits. On this screen, under “Apply & Complete,” click the “Start a New Application” button.

3. Indicate whether or not you already have a Social Security account. If you do, you’ll be asked to sign in. If not, you’ll need to create one. Have your social security number ready, in addition to your driver’s license. You’ll be asked to verify your identity in one of two ways: by live-chatting with a video agent, or by clicking a button that sends a link to your mobile phone. That link will help you submit pictures of the front and back of your driver’s license, as well as a digital “selfie” to confirm your identity. The latter will require you to hold your phone in front of your face with your glasses off, if applicable.

If this is all too difficult—or if you don’t have the right technology—you can always make an appointment to apply in-person by calling Social Security at 1-800-772-1213 (for TTY users, 1-800-325-0778). Or you can contact your local Social Security office here. Realize that wait times might be long, both on the phone and in person.

4. Log in to your Social Security account.

5. Provide some personal information like your name, social security number, date of birth, danger, et cetera.

6. Answer the question on this next screen.

7. Opt in to Medicare Part B, if you so desire.

8. Provide information on your other insurance, if applicable.

9. Sign the application when you’re ready, and then submit it. You’ll no longer be able to modify information in your application after you click “Submit Now.”

Congrats—you made it through!

In about two weeks, you’ll receive your Medicare card in the mail, in a Welcome to Medicare package. Bring the card with you to all medical and pharmacy visits as of the date listed on the front of the card.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
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By Erin Prater
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