Medicare 2026

Does Your Employer Have 20+ Workers? Medicare Guide

# Still Working at 65 in Cleveland Heights? How to Time…

CLEVELAND HEIGHTS, Ohio — More people are working past 65 these days, and that raises a real question: do you sign up for Medicare right away, or stay on your job's health plan? The answer depends on the size of your employer, how your current coverage works, and a few deadlines that are easy to miss.

Here is a plain-English guide to help you decide.

Start with the size of your employer

The biggest factor is how many people work at your company.

• Fewer than 20 employees: Medicare is generally the primary payer at 65, and your job plan pays second. If you skip Part B, you could be left paying most of your medical bills yourself. In this case, most people should enroll in Part A and Part B when first eligible.
• 20 or more employees: Your job plan is usually primary, and Medicare is secondary. Many workers here choose to delay Part B (which has a monthly premium) and stay on their employer plan until they retire.

If you're not sure which category you fall into, ask your HR or benefits office in writing. Get their answer in writing too.

Part A is usually a simple call

Part A (hospital insurance) is premium-free for most people who have worked and paid Medicare taxes for at least 10 years. Because there's no monthly cost, many workers sign up for Part A at 65 even if they keep their job coverage.

One important exception: if you contribute to a Health Savings Account (HSA), you must stop those contributions once any part of Medicare starts, including Part A. Enrolling in Part A can also apply retroactively for up to six months, so time it carefully with your HR team.

Know your enrollment windows

Three windows matter when you're still working:

• Initial Enrollment Period: The 7-month window around your 65th birthday (3 months before, your birth month, and 3 months after).
• Special Enrollment Period (SEP): If you keep employer coverage past 65, you get an 8-month SEP to sign up for Part B once your job or job-based coverage ends — whichever comes first. Missing this window can mean a lifelong late-enrollment penalty.
• Annual Enrollment Period: October 15 – December 7 each year, for Medicare Advantage and Part D changes.

COBRA and retiree coverage do not count as active employer coverage for the SEP. If you go on COBRA at 65, the clock for Part B is still ticking.

What about prescription drugs?

If your employer plan includes drug coverage that Medicare considers "creditable" (at least as good as Part D), you can delay Part D without a penalty. Your plan should send you a creditable coverage notice each year — hang on to it.

If it's not creditable, or you lose it, you'll want to enroll in a Part D plan promptly. For 2026, Part D has a $2,100 annual out-of-pocket cap on covered drugs and a maximum deductible of $615. The old coverage gap ("donut hole") is gone as of 2025. There's also the Medicare Prescription Payment Plan, which lets you spread drug costs across the year in monthly amounts if that helps your budget.

Local context for Cleveland Heights

Cleveland Heights is in Cuyahoga County, where Medicare plan availability — including Medicare Advantage and stand-alone Part D plans — is set at the county level. If and when you do move off your job coverage, you'll have a range of options to compare. You can review what's offered in Cuyahoga County using the plan finder at medicare.gov.

A few things to double-check with HR

Before you decide anything, ask your benefits office:

• Is our plan primary or secondary once I turn 65?
• Is our drug coverage creditable for Medicare purposes?
• Will my premiums or benefits change at 65?
• If I retire mid-year, when exactly does my coverage end?

Their answers can change the math on whether to take Part B now or later.

Watch out for IRMAA

If your household income is on the higher side, keep in mind that Medicare premiums are income-adjusted. In 2026, IRMAA surcharges on Part B and Part D begin above $109,000 for a single filer (higher for joint filers). Medicare looks at your tax return from two years back, so a big work year can affect premiums later.

Where to get personal help

Every situation is different, and there's no shame in asking for a hand. Free, unbiased help is available:

• Medicare.gov for official rules, deadlines, and the plan finder.
• 1-800-MEDICARE (1-800-633-4227), open 24/7.
• Ohio SHIP (OSHIIP): the Ohio Senior Health Insurance Information Program offers free one-on-one counseling. Call 1-800-686-1578.
• Your employer benefits office for how your specific job plan coordinates with Medicare.