Turning 65 · First enrollment
New to Medicare: what to do when you turn 65
If you are new to Medicare, you have a seven-month window around your 65th birthday and a small number of decisions that are hard to undo. Two of the possible penalties last for life. This page walks through the timeline in order, explains when you can safely delay, and shows the one window most people new to Medicare do not know they are spending.
Your Initial Enrollment Period
Everyone new to Medicare gets a seven-month Initial Enrollment Period: the three months before your birthday month, your birthday month, and the three months after.
When you enroll inside that window decides when coverage starts. Enrolling in the three months before your birthday month gets coverage started on the first day of your birthday month. Enrolling during or after your birthday month delays the start.
If your birthday falls on the first of the month, your window shifts a month earlier. It is a small quirk that catches people out.
You may be enrolled automatically
If you are already drawing Social Security or Railroad Retirement benefits when you turn 65, you are generally enrolled in Part A and Part B automatically, and your card arrives about three months before your birthday.
If you are not drawing benefits yet, nothing happens on its own. You have to enroll yourself through the Social Security Administration.
Still working at 65? Read this before you delay
Delaying Part B is sometimes correct and sometimes very expensive. The deciding factor is usually the size of the employer.
Employer with 20 or more employees
The group plan generally pays first and Medicare second. You can usually delay Part B without penalty and enroll later through a Special Enrollment Period when the employment or the coverage ends.
Employer with fewer than 20 employees
Medicare generally becomes the primary payer at 65 even if you keep the group plan. If you have not enrolled in Part B, the group plan may pay as though Medicare had already paid its share, leaving you with the difference. In this situation delaying is usually a mistake.
Coverage that does not protect you
- COBRA is not considered active employer coverage for Part B purposes
- Retiree coverage from a former employer is not either
- Marketplace plans do not protect you from the Part B penalty
- Health savings account contributions must stop before Medicare begins, and Part A can apply retroactively up to six months
People new to Medicare who assume COBRA or retiree coverage counts are the most common penalty cases we see. Confirm with your benefits administrator in writing.
The two permanent penalties
Most Medicare mistakes can be corrected at the next enrollment window. These two cannot.
Part B late penalty
Your premium rises 10 percent for each full 12-month period you could have had Part B and did not. It stays on your premium for as long as you have Part B.
Part D late penalty
Going 63 days or more without creditable drug coverage adds a permanent amount to your Part D premium, based on how many months you went without.
The window most people new to Medicare spend without noticing
Your Medigap Open Enrollment Period runs six months, beginning the first month you are both 65 or older and enrolled in Part B.
During those six months you can buy any Medigap policy sold in your state at the best available rate, with no health questions and no possibility of being declined. It happens once and it never repeats.
After it closes, most states allow insurers to require medical underwriting. A diagnosis you receive at 66 can make a policy unavailable or more expensive for the rest of your life.
This is why the choice between the two structures is worth making deliberately rather than by default. Our Medigap page explains the lettered plans and how premiums are priced.
The related trial right
If you instead join a Medicare Advantage plan when first eligible and change your mind within twelve months, you generally have a guaranteed right to move to Original Medicare and buy a Medigap policy without underwriting. That safety net exists only in your first year.
Choosing your path
Once enrolled in Parts A and B, everyone new to Medicare faces the same fork. Neither answer is better in the abstract.
Original Medicare with a supplement
Any provider nationwide who accepts Medicare, no network, and predictable costs, paired with a separate Part D plan. Higher monthly premium, better for travel.
A Medicare Advantage plan
One plan, usually with drug coverage included, plus a network, an annual out-of-pocket cap, and extra benefits. Lower premium, less provider freedom. Our Medicare Advantage page covers it in detail.
The honest way to decide is to check your own doctors and prescriptions against the specific plans in your county, rather than reasoning about the structures in the abstract.
What higher earners should know
If your income is above certain thresholds, you pay an income-related monthly adjustment on top of the standard Part B and Part D premiums.
It is based on the tax return from two years earlier, so the amount you pay at 65 reflects your income at 63, which is often a working year for someone who has since retired.
If your income dropped because of a life-changing event such as retirement, the death of a spouse, or divorce, you can ask Social Security to use more recent figures. Many people pay the higher amount for a year without realizing they could have asked.
A checklist for anyone new to Medicare
- Mark your seven-month window, counting from three months before your birthday month
- Confirm in writing whether your employer coverage lets you delay Part B
- Stop HSA contributions before Medicare begins, allowing for the six-month retroactive rule
- Enroll in Part A, and Part B unless you have confirmed creditable employer coverage
- Decide between Original Medicare with a supplement or a Medicare Advantage plan
- Arrange drug coverage before the 63-day clock starts running
- If choosing a supplement, act inside your six-month Medigap window
- Note your plan’s Annual Notice of Change each autumn and review
You can compare every plan in your ZIP code at Medicare.gov Plan Compare, and get free unbiased counseling through your State Health Insurance Assistance Program.
Ask before you decide
Questions from people new to Medicare
Do I have to sign up if I am still working?
It depends on employer size. With 20 or more employees you can usually delay Part B safely. With fewer than 20, Medicare generally becomes primary at 65 and delaying can leave you with unpaid claims.
Does COBRA count as employer coverage?
Not for Part B purposes. Neither does retiree coverage. This is one of the most common and most expensive misunderstandings.
When exactly does my coverage start?
If you enroll in the three months before your birthday month, coverage begins the first day of your birthday month. Enrolling later pushes the start date back.
Can I change my mind later?
You can change plans during the enrollment windows. Moving from Medicare Advantage to Medigap later may require medical underwriting, unless you are inside your first-year trial right.
Do I need Part D if I take no medication?
Generally yes, unless you have other creditable coverage. The penalty is permanent, so a low-cost plan usually costs less than waiting.
Does your help cost anything?
No additional fee is charged to you for O’Neal Insurance Group’s guidance. Agents may be compensated by an insurance carrier when an enrollment occurs.
What to gather before you enroll
Having these in front of you turns a confusing hour into a short conversation.
- Your Social Security number and, if you have one already, your Medicare number
- The exact date your current employer or retiree coverage ends, if it is ending
- A written statement from your benefits administrator confirming whether your drug coverage is creditable
- A list of every doctor and specialist you intend to keep seeing
- A list of every prescription with the exact dose and how often you take it
- Your most recent tax return, if you expect the income-related adjustment to apply
The creditable coverage letter is the one people skip and later wish they had. Keep it somewhere you can find it, because you may be asked to produce it years afterwards to prove you should not be penalised.
Important: Enrollment rules, penalties and plan availability vary by situation, by county and by year, and employer coverage rules depend on your specific plan. Nothing on this page is an offer of coverage, a statement of what any specific plan provides, or a determination of your eligibility. We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov, 1-800-MEDICARE, the Social Security Administration, or your State Health Insurance Assistance Program to get information on all of your options.
Official resource
New to Medicare with a health savings account? Read this first
This catches more people who are new to Medicare than any other single rule, and by the time it is noticed the money has usually been contributed.
You cannot contribute to a health savings account for any month in which you are enrolled in any part of Medicare. Not Part B — any part, including premium-free Part A. Contributions made in those months are excess contributions and attract a tax penalty.
What makes this a trap rather than a rule is the retroactivity. When you enroll in Part A after your 65th birthday, coverage is backdated up to six months (never earlier than the month you turned 65). Someone who works to 68, contributes to an HSA throughout, and then signs up is retroactively enrolled for the previous six months — and six months of contributions become excess.
The same backdating applies automatically if you claim Social Security, because Part A enrollment comes with it and cannot be declined while you draw benefits.
The practical answer is to stop HSA contributions at least six months before you intend to enroll in Medicare or claim Social Security. You can still spend the balance afterwards — including on Part B premiums and out-of-pocket costs, which is a legitimate and underused thing to do. It is only new contributions that stop.
Employer coverage when you are New to Medicare: the 8-month window nobody mentions
If you have genuine employer coverage through active employment at a large enough employer, you can usually delay Part B without penalty. When that employment ends, a Special Enrollment Period gives you eight months to enroll.
Here is where it goes wrong. That eight-month clock starts when the employment or the coverage ends, whichever comes first — not when COBRA runs out. COBRA is not active employment coverage. Neither is retiree coverage. People take eighteen months of COBRA, assume they are covered, and discover on enrolling that they are ten months late with a penalty that lasts for life.
The rule also turns on employer size, and the threshold differs depending on whether your Medicare eligibility comes from age or from disability. If you are anywhere near this situation, it is worth one phone call before your birthday rather than a correction afterwards, because there is no appeal against a penalty that was correctly applied.
What it costs to be New to Medicare in 2026
For anyone new to Medicare, Part A is free for most people, because they or a spouse paid Medicare taxes for at least 40 quarters — roughly ten years of work. With 30 to 39 quarters it costs $311 a month, and with fewer than 30 it is $565. The hospital deductible is $1,736 per benefit period, which resets rather than running annually.
Part B costs $202.90 a month at the standard rate for 2026, with a $283 annual deductible and 20 percent coinsurance after that with no ceiling. Part D drug plans carry their own premium, a deductible of no more than $615, and a $2,100 annual cap on what you pay for covered drugs.
If you earned well two years ago, this applies to you
Premiums for higher earners are set from the income on your tax return from two years earlier — so 2026 premiums run on your 2024 income. Single filers above $109,000 and joint filers above $218,000 pay more, rising through five bands to $689.90 a month for Part B at the top, with a matching Part D surcharge.
The two-year lookback lands hardest on people new to Medicare, because the year being measured is usually a working year and the year being lived is usually not. If your income has fallen because you retired, cut your hours, sold a business or lost a spouse, form SSA-44 asks Social Security to use current figures instead. Nobody applies it for you.
The order to do things in when you are New to Medicare
- Three months before your birthday month — check whether your employer coverage lets you delay, and stop HSA contributions if you have not already.
- Enroll in Part A and Part B through Social Security, or confirm you are delaying for a valid reason and have it in writing.
- Choose your path — Original Medicare with a supplement and a drug plan, or a Medicare Advantage plan. Do this before your Medigap window opens, not after.
- Buy the supplement inside the six-month window if that is your route. It is the one time no insurer may decline you or charge more for your health.
- Choose the drug plan against your actual prescriptions, not the premium.
People New to Medicare often do these in the wrong order, and the expensive version is leaving the supplement until after the window has closed. Everything else on this list can be corrected later.
None of this is difficult once someone lays it out in order. It is difficult when you meet it piecemeal, from a mailer here and a relative there, in the three months before a birthday. If you are New to Medicare and would rather have the whole picture in one conversation than assemble it yourself, that is exactly what an appointment is for, and it costs you nothing.
One last thing worth saying to anyone New to Medicare: the deadlines matter more than the plan choice. A plan can be changed next year. A late enrollment penalty and a closed Medigap window cannot.
Check the source, then ask for personal help
Educational information is general. A licensed agent can help with plan comparisons; agents do not provide medical, legal, or official eligibility advice.
Personal guidance · No additional fee
Turning 65 soon? Start before your window opens
Bring your doctors and your prescriptions. We map your dates, confirm whether you can delay, and compare the plans available where you live.
A final word on New to Medicare. Plans change every January — premiums, networks, formularies and extra benefits all move — so it is worth revisiting New to Medicare each autumn rather than renewing on autopilot. If you would like someone to go through New to Medicare with you against your own doctors and prescriptions, call (877) 808-2900. There is no cost and no obligation.
And check New to Medicare against Medicare’s own Plan Compare tool before you enroll. It is free, it lists everything available at your address, and it is the quickest way to confirm that New to Medicare really are the best fit for you.
Medicare reference charts
The charts below cover the ground most questions start from.
