Important Disclaimer: We are not Medicare, the Social Security Administration (SSA), or any federal government agency. To officially sign up for Medicare, you must enroll directly through the Social Security Administration. You can begin your Medicare application here: Sign Up for Medicare at SSA.gov.
Our role is different. We help individuals compare and enroll in Medicare Supplement (Medigap) plans after they have Medicare Parts A and B in place. If you are turning 65 or preparing to retire, this guide will walk you through when and how to sign up for Medicare — and what to do next.
When to Sign Up for Medicare
The most common time to sign up for Medicare is during your Initial Enrollment Period (IEP).
Your Initial Enrollment Period lasts 7 months:
For example, if your 65th birthday is in June, your enrollment window runs from March 1 through September 30.
Learn more directly from Medicare here:
When to Sign Up for Medicare – Medicare.gov
Medicare Enrollment Timeline Chart
The chart below shows how your enrollment window works around your 65th birthday.
| Timeline | What Happens |
|---|---|
| 3 Months Before 65 | Best time to sign up. Coverage typically starts the month you turn 65. |
| Month You Turn 65 | Enrollment still allowed. Coverage timing depends on application date. |
| 1–3 Months After 65 | You can still enroll, but coverage may be delayed. |
| After Initial Enrollment Period | You may face late enrollment penalties unless you qualify for a Special Enrollment Period. |
How to Sign Up for Medicare
You can sign up for Medicare in one of three ways:
1. Online (Fastest and Easiest)
Apply online through Social Security:
Apply for Medicare at SSA.gov
2. By Phone
Call Social Security at 1-800-772-1213.
3. In Person
Visit your local Social Security office.
If you are already receiving Social Security retirement benefits at least four months before turning 65, you will usually be automatically enrolled in Medicare Parts A and B.
Do You Have to Sign Up at Age 65?
Not always.
If you are still working and covered under a large employer health plan (20+ employees), you may qualify for a Special Enrollment Period (SEP) and delay Part B without penalty.
However, COBRA coverage does not count as active employer coverage for Medicare enrollment purposes.
If you delay incorrectly, you may face:
- Permanent Part B late enrollment penalties
- Permanent Part D late enrollment penalties
What Happens After You Sign Up for Medicare?
Once you enroll in Medicare Parts A and B, you’ll need to decide how to receive your coverage:
- Original Medicare + Medigap + Part D
- Medicare Advantage (Part C)
If you choose Original Medicare, you may want to compare Medicare Supplement plans to reduce out-of-pocket costs.
Learn more about Medigap here:
Medigap Plan G Explained
Or compare Medigap vs Medicare Advantage:
Medigap vs Medicare Advantage
Common Medicare Enrollment Mistakes
- Waiting too long to enroll in Part B
- Assuming COBRA counts as employer coverage
- Missing your 7-month Initial Enrollment Period
- Not coordinating Medicare with HSA contributions
Enrolling correctly the first time prevents penalties and coverage gaps.
Key Takeaways: Sign Up for Medicare the Right Way
To sign up for Medicare, apply through Social Security during your Initial Enrollment Period. The best time is 3 months before your 65th birthday month. If you are still working, confirm whether you qualify for a Special Enrollment Period before delaying Part B.
Once Medicare is active, compare your coverage options carefully to avoid unnecessary out-of-pocket costs.
Frequently Asked Questions About Signing Up for Medicare
Do I automatically get Medicare at 65?
You are automatically enrolled only if you are already receiving Social Security retirement benefits at least four months before turning 65.
Where do I sign up for Medicare?
You must enroll through the Social Security Administration at SSA.gov or by calling Social Security directly.
Can I delay Medicare if I’m still working?
Yes, if you have active employer coverage from a company with 20 or more employees. Otherwise, penalties may apply.
What happens if I miss my enrollment window?
You may have to wait until the General Enrollment Period and could face lifetime penalties.
When should I compare Medigap plans?
You should compare Medigap plans once your Part B effective date is set. Your Medigap Open Enrollment Period begins when Part B starts.
Ready to Compare Medigap Plans?
Once you have signed up for Medicare Parts A and B, the next step is protecting yourself from out-of-pocket expenses.
Compare Medicare Supplement (Medigap) plans here:
Get Medigap Quotes
We help you compare carriers, pricing methods, and underwriting considerations so you can enroll confidently.












