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Whether you’re months away from your 65th birthday or plan to work past retirement age, here are the steps to secure your Medicare coverage and avoid costly mistakes.
By
Donna LeValley
published
15 January 2026
in Features
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If you are turning 65 in 2026, you have a critical seven-month window to sign up for Medicare — and missing it can be an expensive mistake. While some people are enrolled automatically, millions of others must take proactive steps to avoid gaps in their health coverage.
With new 2026 changes now in effect — including a $2,100 out-of-pocket cap on prescription drugs and lower negotiated prices for high-cost medications — there has never been a more important time to get your enrollment right. Here is exactly how to sign up, what documents you need, and the deadlines you cannot afford to miss.
This article will focus on those who become eligible for Medicare upon turning 65. There are people under the age of 65 who qualify for Medicare due to disability or a limited slate of diagnoses. This article doesn't address those circumstances.
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Sign upAutomatic enrollment for (most) people already receiving benefits
You will generally be automatically enrolled in both Medicare Part A and Part B if you are already receiving Social Security (SS) benefits at least four months before you turn 65.
There are two groups of 65 year-olds that need to sign-up on their own: those that haven't signed up for Social Security and those who must pay a premium for Part A.
Here's what happens when you are automatically enrolled :
- You will receive your Medicare card in the mail approximately three months before your 65th birthday
- Your coverage will start automatically
What to do if you don't want Medicare- If you are automatically enrolled but choose to decline Part B, usually because you have coverage through a current employer, you must follow the instructions on your welcome package/card to opt out.
You can't disenroll from Part A. This would only be a problem if you are employed and want to continue to contribute to a health savings account (HSA). Otherwise, most people sign up for Part A because it is free for most enrollees, and can serve as secondary hospital insurance that might pick up the costs not covered by your employer-provided health insurance.
Enrollment if you are NOT receiving benefits
If you are not yet collecting Social Security when you become eligible for Medicare at age 65, you must sign up yourself. You have three primary ways to enroll in Part A and Part B through the Social Security Administration (SSA):
Swipe to scroll horizontallyMethod
Where
Process
Online- This is generally the fastest and easiest method.
SSA.gov, the official Social Security Administration website
You can apply online for Medicare Part A and Part B, or Part A only, in about 10 minutes.
By Phone- You can call the SSA to apply or to schedule an appointment to apply in-person
Social Security Administration, 1-800-772-1213 (TTY users 1-800-325-0778)
You can call between 8 am and 7 pm local time M-F. Wait times are shorter earlier in the morning, week and month.
In Person
You can visit a local Social Security office to apply for Medicare
It is best to make an appointment to avoid waiting.
Row 4 - Cell 0 Row 4 - Cell 1 Row 4 - Cell 2Signing up for Medicare Advantage and Part D drug plans
Once you are enrolled in Medicare, you can choose to enroll in a Medicare Advantage plan or top up your original Medicare coverage with a Part D drug plan and/or Medigap insurance.
If you do nothing other than enroll, by default, you will be enrolled in original Medicare. Those in original Medicare should consider adding a Part D plan to defray prescription costs and avoid late enrollment penalties. Even if you don't have many prescriptions now, your needs will change over time. Not adding this policy when you first join Medicare could be a costly mistake. A Medigap policy helps to cover co-payments, coinsurance and other expenses not covered by original Medicare.
Swipe to scroll horizontallyMedicare Part
What it covers
How to enroll
Part C- Medicare Advantage
All-in-one alternative to original Medicare that often includes Part D
You enroll directly with a private insurance company that offers the plan or through Medicare.gov
Part D- Prescription drug coverage
Stand-alone prescription drug coverage
You enroll directly with a private insurance company that offers the plan or through Medicare.gov
Medigap- Medicare supplemental coverage
Helps pay some costs original Medicare doesn't cover
You enroll directly with a private insurance company that offers Medigap policies
Key enrollment periods
Regardless of how you sign up, you must do so during a valid enrollment period to avoid potential late enrollment penalties.
Although most people become eligible for Medicare when they turn 65, not all people decide to enroll at this point. If you have employer-provided coverage through yourself or your spouse, you can delay enrolling until that coverage ends. As long as you have credible coverage, you won't pay late enrollment penalties when you do switch to Medicare.
Swipe to scroll horizontallyPeriod
Time frame
Purpose
Initial Enrollment Period (IEP)
The 7-month window around your 65th birthday: 3 months before, your birthday month, and the three months after.
The first time you can sign up for Part A and Part B.
Special Enrollment Period (SEP)
An enrollment window triggered by life events, most commonly losing job-based health insurance.
Allows you to sign up for Part A and/or Part B outside of the IEP or GEP without penalty.
General Enrollment Period (GEP)
January 1 to March 31 every year.
For those who missed their IEP and do not qualify for a SEP. Coverage starts on July 1 and late penalties will apply.
You're near the finish line
Whether you choose to apply online via SSA.gov, by phone, or through an appointment at your local SSA office, the key is to be proactive. Starting your preparation at least three months before your 65th birthday ensures a seamless transition without gaps in your healthcare.
Ultimately, while the technical steps are your gateway into the system, the peace of mind that comes with secure, lifelong health coverage is the real reward. Once your enrollment is confirmed, your next step is to look forward to your "Welcome to Medicare" visit, where you can partner with your doctor to build a personalized health care prevention plan for the years ahead.
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Donna LeValleyRetirement WriterDonna joined Kiplinger as a personal finance writer in 2023. She spent more than a decade as the contributing editor of J.K.Lasser's Your Income Tax Guide and edited state specific legal treatises at ALM Media. She has shared her expertise as a guest on Bloomberg, CNN, Fox, NPR, CNBC and many other media outlets around the nation. She is a graduate of Brooklyn Law School and the University at Buffalo.
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