Turning 65 comes with a lot of paperwork, and Medicare has its own calendar that does not match your birthday exactly. Missing the right window can mean a gap in coverage or a penalty that could increase your Medicare costs for years to come. Here is when to sign up, what it costs, and how to avoid the common mistakes.
Your Medicare Initial Enrollment Period
Your first chance to sign up for Medicare is called your Initial Enrollment Period. It lasts seven months. It starts three months before the month you turn 65, includes your birthday month, and continues for three months after.
Say Linda turns 65 in June. Her Initial Enrollment Period runs from March through September. She can sign up for Part A (hospital insurance) and Part B (medical insurance) any time during that window.
When you sign up matters, too. If Linda signs up in March, April, or May, her coverage starts on June 1, the first day of her birthday month. If she waits until June, July, August, or September, her coverage starts the first day of the month after she signs up. So if she signs up in August, her coverage begins September 1.
If your birthday falls on the first of the month
There is one exception worth knowing. If your birthday is on the first of the month, Medicare treats you as if you turned 65 the month before. Your seven-month window shifts one month earlier, and so does your coverage start date. If you were born on July 1, your Initial Enrollment Period runs from April through October, and your coverage can start as early as June 1.
Will Medicare Sign You Up Automatically?
Not everyone has to fill out an application. If you are already collecting Social Security or Railroad Retirement Board benefits when you turn 65, Medicare enrolls you in Part A and Part B automatically. Your red, white, and blue Medicare card arrives in the mail about three months before your birthday.
If you are not yet collecting those benefits, perhaps because you are still working, you need to apply yourself. You can do this at SSA.gov, or by calling or visiting your local Social Security office. There is no cost to apply, and the process usually takes less time than people expect.
One group needs to pay attention here: residents of Puerto Rico who get Social Security or Railroad Retirement Board benefits are enrolled in Part A automatically, but not Part B. They must sign up for Part B on their own using Form CMS-40B, available at Medicare.gov.
Choosing Between Original Medicare and Medicare Advantage
Signing up for Part A and Part B is only the first decision. The next one is how you want to receive your coverage. There are two main paths.
Original Medicare is run directly by the federal government. It covers hospital stays (Part A) and outpatient medical care (Part B), and you can add a separate Part D plan for prescription drugs. You can see any doctor or hospital that accepts Medicare, which includes the vast majority of providers nationwide.
Medicare Advantage (Part C) is offered through private insurance companies approved by Medicare. These plans often bundle in drug coverage and sometimes add extras like dental or vision, but they generally work through a network of doctors, similar to an HMO or PPO you may have had through an employer.
Both paths have real trade-offs in cost, provider access, and coverage rules, and the right choice depends on your health needs, your budget, and where you live. Comparing plans available in your specific area is where many people find it helpful to get an outside, independent look at the details rather than sorting through every plan on their own.
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What Medicare Costs in 2026
Cost is often the first question people ask, so here are the current figures.
Part A has no monthly premium if you or your spouse paid Medicare taxes for at least 10 years (this is called premium-free Part A). If you do not qualify for premium-free Part A, you can buy it for either $311 or $565 a month in 2026, depending on your work history.
Part B has a standard premium of $202.90 a month in 2026. Most people pay this amount. Part B also has a yearly deductible of $283 in 2026. Once you meet that deductible, Medicare typically pays 80% of the Medicare-approved amount and you pay 20% for most covered services.
If your income is higher, you may pay more for Part B and Part D through a surcharge called the Income-Related Monthly Adjustment Amount, or IRMAA. For 2026, this applies if your 2024 tax return showed income above $109,000 for an individual or $218,000 for a married couple filing jointly. Medicare bases this year’s premium on your tax return from two years earlier, so a life change like retirement can sometimes qualify you for a lower rate. You can request a review at SSA.gov.
What Happens If You Miss Your Initial Enrollment Period
Life does not always line up with a seven-month window. Medicare has two other paths for people who need them.
Special Enrollment Period
If you are still working past 65 and have health coverage through your job or a spouse’s job, you can delay signing up for Part B without a penalty. Once that employment or coverage ends, you get an eight-month Special Enrollment Period to sign up. This window applies whether or not you choose COBRA continuation coverage. COBRA itself does not extend it or count as qualifying employer coverage. Coverage generally starts the first day of the month after you sign up.
General Enrollment Period
If you miss your Initial Enrollment Period and do not qualify for a Special Enrollment Period, you can still sign up between January 1 and March 31 each year. This is called the General Enrollment Period. Coverage starts the first day of the month after you sign up. The catch is that you may owe a late enrollment penalty, which brings us to the next section.
The Late Enrollment Penalties, With Real Numbers
Medicare’s penalties are not one-time fees. They are usually added to your premium for as long as you have that coverage, so it is worth understanding exactly how they work.
Part B penalty: Your premium can go up 10% for each full 12-month period you were eligible for Part B but did not sign up. Medicare provides an example of a man named Mr. Smith, whose Initial Enrollment Period ended in December 2021. He did not sign up until March 2024, during the General Enrollment Period. That gap covered two full 12-month periods, so his Part B premium carries a 20% penalty for as long as he has Part B, on top of the standard premium.
Part A penalty: If you are not eligible for premium-free Part A and you delay buying it, your premium can go up 10%. You then pay that higher rate for twice the number of years you delayed. Someone who waited two years past their eligibility would pay the higher premium for four years.
Part D penalty: If you go 63 days or more without Medicare drug coverage or other creditable prescription coverage after your Initial Enrollment Period ends, you may owe a Part D penalty. It is calculated as 1% of the national base beneficiary premium, which is $38.99 in 2026, multiplied by the number of full months you went without coverage. The penalty amount is rounded to the nearest $0.10 and recalculated each year using that year’s base premium, so it can shift slightly from year to year even though the percentage stays fixed.
You can avoid all three penalties by signing up on time, or by keeping proof of other creditable coverage if you delay because you are still working.
Reviewing Your Coverage Every Year
Signing up for Medicare is not a one-time task. Each fall, from October 15 to December 7, Medicare holds an Open Enrollment Period. This is your chance to change your health or drug coverage for the year ahead, whether that means switching from Original Medicare to Medicare Advantage, moving from Medicare Advantage back to Original Medicare, or adjusting your drug plan. Changes made during this window take effect January 1.
Even if you are happy with your current plan, it is worth checking each year. Plan costs, covered drugs, and provider networks can all change from one year to the next, and a plan that fit your needs last year may not fit as well this year. This is another point where a second, independent set of eyes on the numbers can catch something you might miss on your own, particularly if your health or medications changed during the year.
A Simple Medicare Enrollment Checklist
- Mark your seven-month Initial Enrollment Period on your calendar, starting three months before your birthday month.
- Find out if you will be enrolled automatically (already collecting Social Security or RRB benefits) or need to apply yourself at SSA.gov.
- Decide between Original Medicare and Medicare Advantage based on your health needs, budget, and preferred doctors.
- If you are still working with employer coverage, confirm your eight-month Special Enrollment Period once that coverage ends, and keep documentation proving you had qualifying coverage.
- Review your coverage every year during Open Enrollment, from October 15 to December 7.
The Bottom Line
The single most important date to remember is the start of your seven-month Initial Enrollment Period. Enrolling during that window, or confirming you’re automatically enrolled, is the easiest way to avoid coverage gaps and costly penalties.
This article is for educational purposes only and is not personalized financial, tax, legal, or medical advice. Medicare rules and dollar amounts can change, and your situation may differ from the examples above. Confirm your specific enrollment dates and costs with Medicare.gov, Social Security, or a qualified advisor before making decisions.
Note Chapter is an affiliate relationship of Holy Schmidt!. This means if you purchase a product or use their service, we earn a small commission. This does not increase your cost.
Chapter Advisory, LLC (“Chapter”) is a private health insurance agency. In California, Chapter does business as Chapter Insurance Services (Lic. No. 6003691). Chapter is not affiliated with or endorsed by any government entity. While Chapter has a database of every Medicare plan option nationwide and can help you to search among all options, it has contracts with many but not all plans. As a result, Chapter does not offer every plan available in your area. Currently, Chapter represents 50 organizations which offer 18,601 products nationwide. You can contact a licensed Chapter agent to find out the number of products available in your specific area. Please contact Medicare.gov, 1-800-Medicare, or your local State Health Insurance Program (SHIP) to get information on all of your options. Enrollment in a plan may be limited to certain times of the year unless you qualify for a Special Enrollment Period or you are in your Medicare Initial Enrollment Period.
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