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When to Enroll in Medicare

Reviewed by Russell Noga, Licensed Medicare Insurance Broker (all 50 states) — Last updated October 8, 2026

Most people should enroll in Medicare during their Initial Enrollment Period, the seven months around their 65th birthday month, ideally in the first three months so coverage starts on the first day of their birthday month.

If you or your spouse has group health coverage from current employment, you may be able to delay Part B without penalty and enroll later during a Special Enrollment Period.

See Medicare plans 2027.

✔ Licensed in all 50 states
✔ Based on CMS 2027 data
✔ Free plan comparison

Key Highlights

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Best time: 3 months before 65.

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Delay only with active work coverage.

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Disability: after 24 months.

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Missing windows costs money.

Compare plans and enroll online

When to Enroll, by Situation

Your Situation When to Enroll Notes
Turning 65, no employer coverage First 3 months of your Initial Enrollment Period Coverage starts your birthday month
Turning 65, on Social Security Automatic Card arrives before your birthday month
Working past 65 with large-employer coverage Part A at 65 (optional); Part B when coverage ends Use the 8-month Special Enrollment Period
Working past 65 with small-employer coverage Usually at 65 Medicare may pay first; ask your employer
Under 65 with disability benefits Automatic after 24 months of benefits ALS has earlier rules
End-stage renal disease Apply based on dialysis or transplant timing Special rules apply

Confirm your situation with Social Security.

Turning 65 in 2027

If you turn 65 in 2027, your Initial Enrollment Period lasts seven months: the three months before your birthday month, your birthday month and the three months after. Signing up during the first three months means your coverage starts on the first day of your birthday month.

Turning 65 Checklist

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Sign up for Part A and Part B, unless you have qualifying employer coverage and choose to delay Part B

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Decide between Medicare Advantage and Original Medicare with Medigap

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Join a drug plan, or a Medicare Advantage plan with drugs, to avoid a Part D late penalty

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If you choose Medigap, buy during your six-month Medigap Open Enrollment Period

Know the Right Time to Enroll in Medicare

Find & Compare Plans Online

Speak with a licensed insurance agent

1-855-398-0716TTY 711

Mon-Fri: 8am-9pm ET

The Cost of Waiting Too Long

10% a Year

Part B penalty for each full 12 months late.

1% a Month

Part D penalty per uncovered month, based on $41.33 for 2027.

Medigap Window

Starts with Part B; missing it can mean health questions.

Before You Delay Part B

Check First

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Confirm the coverage is from current employment, yours or your spouse’s

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Ask whether Medicare or the employer plan pays first

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Check whether you contribute to a health savings account

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Keep written proof of coverage dates

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Plan to enroll within eight months after coverage ends

How Medicare Advantage Works

Medicare Advantage, also called Part C, is a way to get your Medicare benefits through a private insurance company approved by Medicare. The plan covers everything Original Medicare Part A and Part B cover, except hospice care, which Original Medicare still pays. Most plans also include Part D drug coverage, and many may add extras such as routine dental, vision and hearing benefits.

In exchange, Medicare Advantage plans generally use networks of doctors and hospitals, and may require referrals or prior authorization for some services. Every Medicare Advantage plan has a yearly out-of-pocket maximum for covered medical care, which Original Medicare does not have. You keep paying your Part B premium, plus your plan’s premium if it has one.

Feature HMO PPO
Out-of-network care Not covered except emergencies and urgent care Covered at a higher cost
Referrals for specialists Usually required Usually not required
Premiums Usually lower Usually higher
Out-of-pocket maximum In-network limit In-network limit plus a higher combined limit
Best for Lower costs, local care Flexibility, travel, keeping specific doctors

Avoid Medicare Enrollment Penalties

Help Paying Medicare Costs

If your income and savings are limited, two programs can cut your Medicare costs sharply:

Medicare Savings Programs

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Run by your state Medicaid office

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Can pay your Part B premium, and sometimes deductibles and coinsurance

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Income and asset limits vary by state

Extra Help (Part D)

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Run by Social Security

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Lowers Part D premiums, deductibles and copays

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People in a Medicare Savings Program qualify automatically

Those who are eligible for Medicare along with full Medicaid might also have the option of enrolling in a Dual Special Needs Plan. Learn more about help for low-income Part D beneficiaries.

Reading Your Annual Notice of Change

Check Every Line

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Your 2027 premium and deductible

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Copays for doctors, specialists and hospital stays

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The out-of-pocket maximum

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Updates to your formulary, drug tiers and coverage requirements

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Whether your doctors, hospitals and pharmacy are still in network

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Changes to dental, vision, hearing and other extras

Plans must send the Annual Notice of Change by September 30. It is the single most useful document you get each fall, because it tells you exactly how your plan changes on January 1.

Special Enrollment Periods

Outside the fall and early-year windows, you generally need a Special Enrollment Period to change plans. Common reasons include:

You May Qualify If

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Your plan is leaving your area or ending

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You move outside your plan’s service area

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You lose employer or union coverage

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You qualify for Extra Help or a Medicare Savings Program, or your Medicaid status changes

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You want to join a 5-star plan, once a year

Each Special Enrollment Period has its own time limit, so act as soon as the event happens.

Prior Authorization and Referrals

Most Medicare Advantage plans require prior authorization for some services, such as certain surgeries, advanced imaging, skilled nursing stays and some drugs. Your doctor usually requests it, but ask whether a planned service needs approval so a denial does not surprise you.

If a request is denied, you or your doctor can appeal. Medicare rules set deadlines for plans to decide, with faster deadlines when waiting could seriously harm your health.

Emergency, Urgent and Out-of-Area Care

Every Medicare Advantage plan covers emergency care and urgent care anywhere in the U.S., in or out of network, and you do not need prior approval for an emergency. Routine care away from home is a different story: HMOs generally do not cover it, while PPOs cover out-of-network care at a higher cost.

If you spend months away from home each year, ask each plan how it handles care in your second location. It is one of the most common reasons people switch plans mid-year.

Appeals and Complaints

If your plan denies a service, a drug or payment for care, you have the right to appeal. The plan’s denial notice explains how. There are several levels of appeal, starting with the plan and moving to independent reviewers.

For problems that are not about coverage, such as customer service or wait times, you can file a grievance with the plan. You can also contact 1-800-MEDICARE or your State Health Insurance Assistance Program for help.

The 2027 Part B Premium

The Part B premium is the one big number not released with the plans. CMS normally announces it in November. The 2026 Medicare Trustees Report projects a 2027 standard premium of about $209.50 a month and a deductible of about $292, up from $202.90 and $283 in 2026. You keep paying it with Medicare Advantage.

If You Miss December 7

If you miss the Annual Enrollment deadline, your current plan renews automatically for 2027, with the changes in your Annual Notice of Change. If you are in Medicare Advantage, you get one more chance from January 1 to March 31, 2027, to switch Medicare Advantage plans or return to Original Medicare and join a Part D plan.

Telehealth

Many Medicare Advantage plans may cover telehealth visits for some services, sometimes at a lower copay than an office visit. Telehealth is convenient for follow-ups and minor issues, but it does not replace confirming that your regular doctors are in network.

Pros and Cons of Medicare Advantage

Advantages

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Often a low or $0 premium

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A yearly out-of-pocket maximum

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Drug coverage usually included

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Many plans may include dental, vision and hearing benefits

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One card and one plan

Tradeoffs

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Networks; HMOs require in-network care except emergencies

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Prior authorization and referrals are common

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Copays add up if you use a lot of care

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Plans and networks can change every year

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Switching to Medigap later may require health questions

Special Needs Plans

Special Needs Plans (SNPs) are Medicare Advantage plans built for specific groups. Benefits, networks and drug lists are designed around the members they serve, and many include care coordinators. For 2027, Special Needs Plans are one of the few areas where large insurers are adding plans, even as they cut PPOs.

Type Who Qualifies What Is Different
Dual Special Needs Plan (D-SNP) People with both Medicare and Medicaid Coordinates both programs; often very low costs and added benefits
Chronic Condition SNP (C-SNP) People with qualifying conditions such as diabetes, heart failure or chronic lung disease Doctors, drugs and programs built around the condition
Institutional SNP (I-SNP) People living in a nursing home or who need that level of care at home Care delivered where the member lives

Star Ratings

Medicare rates every Medicare Advantage and Part D plan from 1 to 5 stars each fall, based on things like preventive care, how well the plan manages chronic conditions, member complaints, customer service and drug pricing accuracy. The ratings are shown in Medicare Plan Finder.

Using Star Ratings

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A rating of 4 stars or higher is generally a good sign of quality and service

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Five-star plans have a special enrollment period, so you can switch into one once during the year

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New plans may not have a rating yet, which is not a bad sign by itself

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Ratings measure the plan overall, not how well it covers your specific doctors and drugs

If a Drug Is Not Covered

Sometimes a drug you take is not on a plan’s 2027 formulary, or it carries a rule like prior authorization. You still have options:

If Your Drug Is Not Covered

1

Ask for a transition fill. In the first 90 days of a new plan year or a new plan, plans generally must give you a temporary supply of a drug you were already taking, so you have time to switch or request an exception.

2

Ask your doctor about alternatives. A covered drug in the same class may work as well and cost less.

3

Request a formulary or tiering exception. Your doctor submits a statement explaining why you need the drug or a lower copay. Plans must decide within set time limits.

4

Appeal a denial. If the plan says no, you can appeal, and there are several levels of review.

See steps to appeal a Medicare Part D denial.

Part D Drug Coverage in 2027

$700

Maximum 2027 Part D deductible, up from $615.

$2,400

2027 Part D out-of-pocket cap, up from $2,100.

About $36

Average 2027 standalone Part D premium, up less than $1 (CMS).

$7

Projected average drug portion of a Medicare Advantage premium for 2027, down from $11.32.

Tier Typical Drugs Typical Cost
Tier 1 Preferred generics Lowest copay
Tier 2 Generics Low copay
Tier 3 Preferred brand-name drugs Moderate copay
Tier 4 Non-preferred drugs Higher copay or coinsurance
Tier 5 Specialty drugs Highest coinsurance

Tier structures vary by plan. Check each plan’s formulary.

Your Medigap Open Enrollment Period in Detail

Your six-month Medigap Open Enrollment Period starts the first month you are both 65 or older and enrolled in Part B. It happens only once and cannot be restarted. During it, insurers must sell you any Medigap plan they offer in your state, at the same price as people in good health.

If you keep working past 65 with employer coverage and delay Part B, your Medigap Open Enrollment Period waits until you enroll in Part B. Enrolling in Part B early, when you do not need it, starts the clock and can waste this protection.

Switching From Medicare Advantage to Medigap

Step by Step

1

Check whether you have a guaranteed issue right. For example, your plan is ending or you are within your first year of Medicare Advantage.

2

If not, check your state’s rules. Some states give extra rights; most allow health questions.

3

Apply for Medigap before you leave Medicare Advantage. Make sure you are approved first.

4

Join a Part D plan. Medigap does not cover drugs.

5

Leave Medicare Advantage at the right time. During Annual Enrollment or the January to March window.

Medigap With Employer or Retiree Coverage

If you have coverage from a current employer, you may not need Medigap yet, and delaying Part B can preserve your Medigap Open Enrollment Period for later. Retiree coverage is different: it may work like a supplement, so compare it with Medigap before dropping it, because you may not be able to get retiree coverage back.

When employer or union coverage that pays after Medicare ends, you generally have a guaranteed issue right to buy certain Medigap plans.

Pre-Existing Condition Waiting Periods

If you buy Medigap during your open enrollment period or with a guaranteed issue right, you generally cannot be denied or charged more for health conditions. However, if you did not have creditable coverage before, an insurer may impose a waiting period of up to six months before covering costs for a pre-existing condition. Prior creditable coverage reduces or removes that waiting period.

The 30-Day Free Look Period

If you replace one Medigap policy with another, you generally get 30 days to decide whether to keep the new policy. Pay the premiums for both during that time, and do not cancel your old policy until you are sure about the new one.

How to Read a Medigap Quote

Check Each Quote For

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Plan letter, so you compare like with like

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Monthly premium and any first-year or enrollment discount

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Pricing method: community, issue-age or attained-age

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Household or payment discounts applied

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Effective date and any application conditions

If a quote includes an introductory discount, ask what the premium becomes after it ends.

Common Medigap Mistakes

Avoid These

1

Missing your open enrollment period. Later, health questions may apply.

2

Choosing on today’s price alone. Pricing method and rate history matter.

3

Forgetting Part D. The late penalty is permanent.

4

Dropping Medigap for Medicare Advantage without a plan to return. Getting back may require health questions.

5

Canceling a policy before a new one is approved. You could be left without coverage.

Medigap and Medicaid

If you have full Medicaid, you generally do not need Medigap, and insurers generally cannot sell you a policy that duplicates Medicaid benefits. If you qualify for a Medicare Savings Program, it may pay your Part B premium and, in some cases, deductibles and coinsurance; check whether a Medigap policy still adds value for you.

What Original Medicare Leaves You to Pay

A Medicare Supplement plan is built to cover the gaps in Original Medicare. These are the costs it can pick up:

Original Medicare Gap What It Means for You Covered By
Part A deductible A deductible for each hospital benefit period, not once a year. It was $1,736 in 2026. Plans B, C, D, F, G and N in full; K, L and M in part
Part A hospital coinsurance Daily charges after day 60 of a hospital stay, rising after day 90 All 10 plans, plus 365 extra hospital days
Part B deductible A yearly deductible before Part B pays. It was $283 in 2026. Only Plans C and F
Part B coinsurance Usually 20% of the approved amount, with no yearly cap All plans (K and L in part, N with copays)
Part B excess charges Up to 15% above the approved amount from doctors who do not take assignment Plans F and G
Skilled nursing coinsurance Daily charges from day 21 to day 100 of a covered stay Plans C, D, F, G, M and N (K and L in part)
Emergency care abroad Original Medicare generally does not cover care outside the U.S. Plans C, D, F, G, M and N, up to plan limits

No cap without a supplement: Original Medicare has no out-of-pocket maximum. Without a Medigap plan or other coverage, there is no limit to the 20% you can owe on Part B services.

All 10 Medigap Plans Compared

Federal law sets exactly what each plan letter covers, so the same letter has the same benefits from every insurer in your state.

Benefit A B C* D F* G K L M N
Part A coinsurance and hospital costs up to 365 extra days Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes
Part B coinsurance or copayment Yes Yes Yes Yes Yes Yes 50% 75% Yes Yes***
First 3 pints of blood Yes Yes Yes Yes Yes Yes 50% 75% Yes Yes
Part A hospice coinsurance or copayment Yes Yes Yes Yes Yes Yes 50% 75% Yes Yes
Skilled nursing facility coinsurance No No Yes Yes Yes Yes 50% 75% Yes Yes
Part A deductible No Yes Yes Yes Yes Yes 50% 75% 50% Yes
Part B deductible No No Yes No Yes No No No No No
Part B excess charges No No No No Yes Yes No No No No
Foreign travel emergency (up to plan limits) No No 80% 80% 80% 80% No No 80% 80%
Out-of-pocket limit None None None None None None Yes** Yes** None None

*Plans C and F can only be bought by people who were eligible for Medicare before January 1, 2020. **Plans K and L have a yearly out-of-pocket limit that Medicare sets each year; after you reach it, the plan pays 100% of covered services for the rest of the year. ***Plan N pays all Part B coinsurance except copays of up to $20 for some office visits and up to $50 for emergency room visits that do not lead to an inpatient admission. Massachusetts, Minnesota and Wisconsin standardize their plans differently.

Getting Help

You do not have to compare plans alone, and you should not have to pay for help. These are the free options:

Free Help Comparing Plans

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Medicare Plan Finder on Medicare.gov, available any time

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1-800-MEDICARE (1-800-633-4227), available 24 hours a day, seven days a week

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Your State Health Insurance Assistance Program (SHIP), which offers free, unbiased counseling

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A licensed insurance agent or broker, who can compare plans from several insurers at no cost to you

Before any call, have your Medicare card, your list of drugs and doses, your doctors and your preferred pharmacies ready. It turns a long conversation into a short one.

Bottom Line

The Bottom Line

Enroll during your Initial Enrollment Period unless active employer coverage lets you delay, and plan Medigap and Part D around your Part B start.

Compare plans and enroll online

Frequently Asked Questions

➤ When should I enroll in Medicare?

Most people should enroll during their Initial Enrollment Period, the seven months around their 65th birthday month. Signing up in the first three months means coverage starts on the first day of your birthday month, with no gap.

➤ Am I enrolled in Medicare automatically?

Yes, if you already receive Social Security or Railroad Retirement benefits when you turn 65, or after 24 months of disability benefits. Your Medicare card arrives in the mail. Otherwise, you must apply through Social Security.

➤ Can I delay Medicare if I am still working?

If you or your spouse has group coverage from current employment, you can usually delay Part B without penalty. Many people still take premium-free Part A. Ask your employer how its plan works with Medicare first.

➤ What happens if I enroll late?

You may owe a Part B penalty of 10% for each full 12-month period you went without it, usually for life, and a Part D penalty for months without creditable drug coverage. You may also face gaps in coverage.

➤ When should I enroll if my employer coverage ends?

Sign up for Part B within eight months after your employment or group coverage ends, whichever comes first. It is safest to enroll before coverage ends so there is no gap. COBRA does not extend this window.

➤ Can I get Medicare before 65?

Yes, if you have received Social Security disability benefits for 24 months, have ALS, or have end-stage renal disease. Each has its own rules for when coverage starts. Social Security can confirm your dates. Coverage for people with ALS starts sooner than for other disabilities.

➤ When should I buy Medigap?

Plan to buy Medigap during your six-month Medigap Open Enrollment Period, which starts when you are 65 or older and enrolled in Part B. During it, insurers cannot deny you or charge more for health conditions.

➤ When should I join a Part D plan?

Join when you first get Medicare, during your Initial Enrollment Period, unless you have creditable drug coverage. Going 63 days or more without coverage can mean a lifelong penalty of 1% of $41.33 per uncovered month for 2027.

➤ Does enrolling in Medicare affect a health savings account?

Yes. Once Medicare coverage starts, including premium-free Part A, you can no longer contribute to a health savings account. Part A can be backdated, so stop contributions ahead of time and ask a tax advisor.

➤ Who can help me decide when to enroll?

Social Security can confirm eligibility and dates, your State Health Insurance Assistance Program (SHIP) offers free counseling on timing, and a licensed agent can help you plan Medigap, Part D or Medicare Advantage. Ask before your 65th birthday month.

Have Questions?

Speak with a licensed insurance agent

1-855-398-0716

TTY users 711

Mon-Fri: 8am-9pm ET

Find & Compare Plans Online

Speak with a licensed insurance agent

1-855-398-0716TTY 711

Mon-Fri: 8am-9pm ET

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