Medicare Enrollment Checklist: Steps, Deadlines and Documents

Medicare Enrollment Checklist: Steps, Deadlines and Documents

To enroll in Medicare, work through five things in order. Confirm your enrollment window. Gather your documents. Apply for Part A and Part B online through Social Security. Choose how you will fill the gaps (Medigap, or Medicare Advantage, plus drug coverage). Then put a yearly review on your calendar. This checklist covers each step, including how to apply for a Medigap policy once Part B is in place.

TL;DR

• Most people get a seven-month Initial Enrollment Period: three months before the month you turn 65, the birthday month, and three months after. Delaying can mean a coverage gap and a lifelong Part B penalty.
• Apply for Part A and Part B online through your my Social Security account. It is the fastest route.
• Medigap has its own one-time six-month Open Enrollment Period that starts when you are 65 or older and have Part B. Protections are strongest during that window.
• Before you pick any plan, check your doctors, your prescriptions, your pharmacy and your total yearly costs.
• Review your coverage every fall. Plans change, and so can your health.

Table of Contents

• Step 1: Find your enrollment window
• Step 2: Gather what you need before you apply
• Step 3: Apply for Part A and Part B
• Step 4: Choose how you will fill the gaps
• Step 5: How to enroll in Medigap
• Step 6: Review your coverage every year
• How we can help
• Free, impartial places to get help
• The full checklist on one page
• FAQ
• Sources

Step 1: Find your enrollment window

Your deadline depends on your situation, so start here.

Turning 65 with no job-based coverage. Medicare.gov says most people sign up for Part A and Part B when first eligible. That window generally starts 3 months before you turn 65 and ends 3 months after the month you turn 65. Signing up in the first three months gives you the smoothest start.

Still working, or covered by a spouse’s job. If you or your spouse have current employer group health coverage, you can generally enroll in Part B while covered or within 8 months after the job or coverage ends. The 8-month Special Enrollment Period starts when employment ends, even if other coverage continues.

Not every kind of coverage counts. Medicare.gov states that COBRA, retiree coverage and Marketplace coverage do not qualify for the employment-based Special Enrollment Period. If you are leaving a job and considering COBRA, read our guide to COBRA versus Medicare before you decide.

Missed your window. The General Enrollment Period runs January 1 through March 31 each year. Medicare.gov says coverage generally starts the month after you enroll and a late-enrollment penalty may apply.

Why timing matters. According to Medicare.gov, delaying past your first eligible period can mean waiting for coverage and paying a monthly Part B penalty for as long as you have Part B, unless an exception applies. Our article on the Medicare late enrollment penalty explains how it works. If you want the full picture of every period, see Medicare enrollment periods, explained simply.

A quick window checker

Step 2: Gather what you need before you apply

A few minutes of preparation keeps the application short. Have these ready:

• Your Social Security number
• Your date and place of birth
• Your citizenship or lawful residence status
• Your current health insurance details, including any employer plan
• Dates your employment or group coverage started and ended, if you are delaying Part B
• A list of your doctors, your pharmacy and every prescription with its dose

The last item is not for the Social Security application. You will need it in Step 4 when you compare plans.

Forms you may run into

Most people never touch paper. Still, the forms are worth knowing. Medicare.gov says that if you are enrolling in Part B after job coverage, you apply online and submit form CMS-L564, which your employer completes. If the employer cannot complete it, you fill out Section B and submit proof of your coverage.

CMS also lists other forms for specific cases (Original Medicare eligibility and enrollment):

• CMS-18-F-5: for people without Part A who want Part A and possibly Part B
• CMS-40B: for people who have Part A and want Part B
• CMS-4040: for people not entitled to Social Security or Railroad Retirement benefits who want Part B
• CMS-43: for end-stage renal disease (ESRD) enrollment
• CMS-10797: for certain exceptional-condition Special Enrollment Periods

If your situation involves kidney failure or ALS, our pages on ESRD and Medicare and ALS and Medicare walk through the basics.

Step 3: Apply for Part A and Part B

Medicare.gov calls applying online through Social Security the easiest and fastest way to enroll. You use a secure my Social Security account.

1. Create or sign in to your my Social Security account.
2. Start the Medicare application and enter your personal and coverage details.
3. If you are delaying Part B because of employer coverage, submit form CMS-L564 with it.
4. Submit, and save your confirmation.
5. Watch your mail for your Medicare card and your start date.

If you would rather talk it through, we do enrollment support for people in Northern Illinois and Southern Wisconsin. See our Medicare enrollment assistance page.

Step 4: Choose how you will fill the gaps

Original Medicare (Parts A and B) does not cover everything. Most people pick one of two paths, and add drug coverage.

Path one: Original Medicare plus Medigap plus Part D. You keep Original Medicare, buy a Medicare Supplement (Medigap) policy to help with your share of costs, and join a separate Part D drug plan.

Path two: Medicare Advantage (Part C). A private plan bundles Parts A and B, usually with drug coverage and sometimes extra benefits.

Neither is right for everyone. What matters is how each fits your doctors, your prescriptions, your budget and how much you travel. Our simple guide to getting started with Medicare covers the pieces if the alphabet soup is new.

What to check on any plan

Medicare.gov’s guidance on joining a plan points to these checks:

• Compare the plans available where you live.
• Enter your prescriptions to see what each plan covers.
• Verify that your doctors and pharmacies are in the plan.
• Review premiums, deductibles and estimated yearly costs.
• Confirm the plan has the benefits you need.
• Coordinate with any employer or other insurance you keep.
• If you spend part of the year elsewhere, verify coverage there too.

Benefits are worth a close look, because extras differ from plan to plan. Dental is a common one: this overview of Medicare dental coverage explains when it is covered and how claims work.

Don’t forget drug coverage

If you already have prescription coverage, ask whether it is creditable. Medicare.gov says that going 63 days or more without creditable drug coverage can generally create a Part D late-enrollment penalty that lasts as long as you have drug coverage. Our explainer on Part D costs and formularies shows what to compare.

Step 5: How to enroll in Medigap

Medigap works differently from Part A and Part B. You do not apply through Social Security. Once you have Part B, you apply directly to an insurance company that sells the lettered Medigap plan you want in your state, according to Medicare.gov’s Choosing a Medigap Policy.

Medigap checklist

1. Confirm you have Part B. You need it before a Medigap policy can start.
2. Note your Medigap Open Enrollment Period. It is a one-time, six-month window that begins when you are 65 or older and have Part B. Medicare.gov calls it the best time to buy.
3. Decide which lettered plan you want. Standardized plans offer the same basic benefits no matter which company sells them, so you can compare companies on price and service.
4. Get quotes from several insurers in your state. Prices for the same plan can differ.
5. Complete the application carefully. Answer every question accurately.
6. Keep records. Save the policy summary and your payment records, and confirm the effective date in writing.

Why the six-month window matters

During that period, insurers generally must sell you any plan they offer without medical underwriting or health-based price increases. Outside protected periods, Medicare.gov says an insurer may use medical underwriting, so you might not be able to buy a policy or might pay more. Guaranteed-issue rights can limit that, and they vary by qualifying event and by state. Some states also protect people under 65.

If you have been denied coverage or think your rights were not honored, contact your State Insurance Department. If you want help comparing Medigap options, our Medicare Supplement and Medigap guidance page explains how we work with it.

Step 6: Review your coverage every year

Enrolling is not a one-time task. Plans change their costs, networks and drug lists each year. Medicare.gov says Open Enrollment happens every year from October 15 to December 7, and changes made then take effect January 1. During that period you can change your Medicare Advantage or drug plan, or switch between Original Medicare and Medicare Advantage.

Here is a yearly routine:

• Read your Annual Notice of Change. Your plan sends it in the fall. It lists what is changing in costs, benefits and coverage.
• Compare plans at Medicare.gov/plan-compare. Your Yearly Medicare Review lists what to look at: costs, benefits, prescription coverage, providers and networks, estimated out-of-pocket costs and quality ratings.
• Update your prescription list. A new medication can change which plan costs you least.
• Re-check your doctors. Networks shift, and so do your own needs.
• Decide, then act before the deadline. The plan must receive your request by December 7.

If you switch to Original Medicare, Medicare.gov notes you may need a separate drug plan and may want to add Medigap, so start with Step 5 early.

How we can help

Almond Insurance is a Medicare agency in Rockford, Illinois. We help individuals and caregivers in Northern Illinois and Southern Wisconsin with new-to-Medicare guidance, comparing Medicare Advantage, Medicare Supplement and Part D plans, and yearly coverage reviews. We explain things in plain language, step by step, and our advice does not cost you anything directly: we are paid by the insurance carrier if you enroll in a plan through us.

If you are turning 65, retiring or just want a second look at your current plan, start with our new-to-Medicare guidance, or see what happens next. If you already have a plan, our annual coverage review is built for exactly this checklist. You can also browse all our services.

Free, impartial places to get help

You have options beyond an agency, and you should know them. Medicare.gov and 1-800-MEDICARE answer general questions. Your State Health Insurance Assistance Program (SHIP) offers free, personalized counseling, and you can find yours at shiphelp.org. For Medigap rights or a coverage denial, contact your State Insurance Department. These are all listed in Choosing a Medigap Policy.

The full checklist on one page

• [ ] Identify your window: Initial Enrollment Period, 8-month Special Enrollment Period or General Enrollment Period
• [ ] Check whether your current coverage qualifies (COBRA and retiree plans generally do not for Part B)
• [ ] Gather your Social Security number, birth details, citizenship status and employment dates
• [ ] Apply for Part A and Part B online through Social Security
• [ ] Submit CMS-L564 if you are enrolling in Part B after job coverage
• [ ] List your doctors, pharmacy and prescriptions
• [ ] Choose Original Medicare with Medigap and Part D, or Medicare Advantage
• [ ] Mark your six-month Medigap Open Enrollment Period if you want a Medigap plan
• [ ] Save your policy summary, payment records and effective dates
• [ ] Review your plan every fall

FAQ

When should I start enrolling in Medicare?

Start three months before the month you turn 65. Your window runs from then until three months after your birthday month. Signing up early gives your coverage time to begin when you want it to, and avoids penalties tied to late enrollment.

How do I apply for Medicare?

Apply online through Social Security with a my Social Security account. It is the easiest and fastest route, according to Medicare.gov. If you are delaying Part B because of job coverage, you will also submit form CMS-L564, completed by your employer.

How do I enroll in Medigap?

After you have Part B, apply directly to an insurance company that sells the plan letter you want in your state. The best time is the one-time six-month Medigap Open Enrollment Period, which starts when you are 65 or older and have Part B. Keep your policy summary and payment records.

Can I be turned down for Medigap?

Outside protected periods, insurers in many cases can use medical underwriting, so you might be denied or pay more. Guaranteed-issue rights can limit that, and they vary by state and situation. Your State Insurance Department can explain your rights.

Where can I get free help with Medicare?

Call 1-800-MEDICARE or visit Medicare.gov. For free one-on-one counseling, contact your State Health Insurance Assistance Program through shiphelp.org.

Sources

• When can I sign up for Medicare? | Medicare.gov
• When to sign up for Medicare | Social Security Administration
• When does Medicare coverage start? | Medicare.gov
• Ready to sign up for Part A & Part B | Medicare.gov
• Original Medicare (Part A and B) Eligibility and Enrollment | CMS
• Joining a plan | Medicare.gov
• Choosing Medicare drug coverage | Medicare.gov
• Choosing a Medigap Policy | Medicare.gov
• Open Enrollment | Medicare.gov
• Your Yearly Medicare Review | Medicare.gov
• Medicare dental coverage overview

Recommended

• Medicare Enrollment Periods, Explained Simply
• Medicare Late Enrollment Penalty: Costs and How to Avoid It
• ALS and Medicare: Eligibility and Enrollment Basics
• A Simple Guide to Getting Started with Medicare