Jesse Smedley is a Principal of Oakbridge Insurance and the founder of iHealthBrokers. He founded iHealthBrokers in 2007, and Oakbridge acquired iHealthBrokers in 2025. He has spent nearly two decades teaching people how to save money on their health insurance and navigate Medicare, and he is the author of Medicare A to Z: Your Roadmap to Medicare.
If you plan to keep working past 65, you have a decision to make that a lot of people get wrong: do you enroll in Medicare now, or wait? Get it right and you could save money for years. Get it wrong and you could end up with a penalty that lasts for the rest of your life, or lose a tax break you didn’t know you had.
Automatic Enrollment at 65
Many people assume they have to sign up for Original Medicare at 65. That isn’t always true. But if you’re already getting Social Security or Railroad Retirement benefits, you’ll be enrolled in Original Medicare automatically, and your card will arrive in the mail. The real question is whether you should keep it, especially Part B.
Why Your Employer’s Size Matters
If you’re still working, the size of your employer decides how your coverage works with Medicare.
20 or More Employees
If your employer has 20 or more employees, your group health plan pays first and Medicare pays second if you enroll. In this case, it’s often easier to keep your employer coverage and delay Part B.
Fewer Than 20 Employees
If your employer has fewer than 20 employees, Medicare pays first and your employer plan pays second. If you don’t enroll in Medicare on time, your employer plan may pay very little or nothing, and billing can get complicated. In most cases, you’ll want to enroll in Part A and Part B when you’re first eligible.
Compare Your Employer Coverage With Medicare
Before you decide, compare your current plan with Medicare side by side. Look at monthly premiums, deductibles, copays, coinsurance and the out-of-pocket maximum. Keep in mind that Original Medicare has no out-of-pocket maximum on its own.
Part A and Part B Premiums
Most people pay no monthly premium for Part A, but Part B has one. In 2026, the standard Part B premium is $202.90 per person, and it’s higher if your income is above certain limits. If your employer plan also covers your spouse or dependents, factor that in, because Medicare only covers you.
Medicare Deductibles
Original Medicare has two separate deductibles. In 2026, the Part A deductible is $1,736 per benefit period and the Part B deductible is $283 per year. On top of that, there are copays and coinsurance. See every 2026 number on our Medicare costs page.
Should You Delay Part B?
Once you’ve compared the numbers, you may decide to delay Part B for now. Most people still take Part A when they’re first eligible because it usually has no monthly premium.
You get premium-free Part A if you or your spouse worked and paid Medicare taxes for at least 40 quarters, which is about 10 years. If you have fewer than 40 quarters, you pay a monthly premium. In 2026, that’s $311 per month with 30 to 39 quarters and $565 per month with fewer than 30. Once you reach 40 quarters, the premium goes away.
The HSA Catch
There’s one big exception to taking Part A right away: a health savings account (HSA). HSAs are popular with people planning an early retirement, and with anyone who wants the triple tax advantage.
An HSA is your account with your money in it. Contributions are made before taxes, which lowers your taxable income, and growth and qualified withdrawals are tax-free.
Once you enroll in any part of Medicare, including Part A, you can no longer contribute to an HSA. There’s a second catch: if you sign up for Part A after 65, your Part A coverage can start up to 6 months earlier than the date you enroll. Any HSA contributions you made during those months may no longer be tax-free, which can mean a surprise tax bill.
If you enroll right when you turn 65, you don’t need to worry. Part A won’t be backdated to before your 65th birthday. If you’re delaying, stop HSA contributions at least 6 months before you plan to enroll.
What Happens When You Retire?
When you finally retire, it’s time to enroll if you haven’t already. You can sign up through Social Security online, by phone or in person. You get an 8-month Special Enrollment Period that starts the month after your job or your employer coverage ends, whichever happens first.
If you miss that window, you may have to wait for the General Enrollment Period, which can leave you without coverage for months. You could also owe a late enrollment penalty.
And don’t count on COBRA to protect you. COBRA doesn’t count as coverage based on current employment, so it doesn’t extend your Special Enrollment Period.
Late Enrollment Penalties
Part B Late Enrollment Penalty
If you don’t enroll during your 8-month window, you could face a Part B late enrollment penalty. It isn’t a one-time fee. It’s added to your monthly premium for as long as you have Part B.
The penalty is 10% of the standard Part B premium for each full 12-month period you could have had Part B but didn’t, and didn’t have coverage based on current employment. After a few years, that can add a lot to your monthly premium.
Part D Late Enrollment Penalty
There’s a Part D penalty too. If you go 63 days or more in a row without Part D or other creditable drug coverage after your Initial Enrollment Period ends, you may owe a penalty for as long as you have drug coverage.
The Part D penalty is usually smaller, often a few dollars a month, but it’s completely avoidable. Many low-cost Part D plans are available, and some areas have plans with no monthly premium. Even if you don’t take prescriptions today, you may need them next month.
So, Should You Wait to Enroll in Medicare?
If you’re asking “Can I wait to enroll in Medicare?” the answer is usually yes, as long as you have coverage through current employment. If you’re asking “Should I wait?” the answer depends on your situation.
Think about your employer’s size and whether its coverage is better or worse than Medicare. Think ahead to Medicare Supplement plans, too. Your best chance to get one without health questions is your 6-month Medigap Open Enrollment Period, which starts once you’re 65 and enrolled in Part B. Plan your drug coverage so you avoid the Part D penalty. And if you contribute to an HSA, plan 6 months ahead so you don’t get hit with a tax bill.
Not sure which way to go? Our Turning 65 guide walks through every deadline, or you can get your free quotes and talk with a licensed broker at (866) 260-9829.
