Still working at 65?
The wrong move here gets expensive fast.

Turning 65 doesn’t always mean you enroll in Medicare right away. But the rules around delaying are where people get burned, and the mistakes aren’t small.

I had a client who used the wrong wording with Social Security, went in for a heart stent the next month, and owed $10,000 that almost didn’t get covered. It’s all about the rules, and knowing them before you act.

Before you delay Part B, let’s look at what actually applies to your situation.

Still working at 65? The wrong move here gets expensive fast

Turning 65 doesn’t always mean you enroll in Medicare right away. But the rules around delaying are where people get burned, and the mistakes aren’t small.

I had a client who used the wrong wording with Social Security, went in for a heart stent the next month, and owed $10,000 that almost didn’t get covered. It’s all about the rules, and knowing them before you act.

Before you delay Part B, let’s look at what actually applies to your situation.

Delaying Part B: when it's allowed and when it's a trap.

If you have creditable coverage through an employer, you may be able to delay Part B without a penalty. Creditable coverage means your employer plan is considered as good as Medicare. But not all coverage qualifies, and assuming yours does without checking is how the penalty starts.

Employer size changes everything.

The rules are different depending on how many employees your company has. That single detail can change whether you should enroll now or wait. Because Medicare is not cookie-cutter, what worked for a coworker may not work for you.

The HSA conflict most people miss.

If you have a Health Savings Account through work, enrolling in Medicare affects your ability to contribute to it. This catches people off guard every year. If you’re still contributing to an HSA at 65, this is a detail you need to understand before you enroll.

Ask Toni

Frequently Asked Questions

Can I delay Part B if I'm still working?

Often yes, if you have creditable employer coverage and your employer is large enough. But it depends on your specific situation, so confirm before you assume.

It’s coverage your plan considers as good as Medicare’s. If yours is creditable, you can usually delay without a penalty. If it isn’t, the penalty clock may already be running.

Once you enroll in Medicare, you can no longer contribute to an HSA. If you’re still contributing, plan around this before enrolling.

Know more

Read the related articles:

Your next step:

Don't guess your way through working past 65.

The rules around delaying Part B, creditable coverage, and your Special Enrollment Period are exactly where the costly mistakes happen. The Medicare 2026 Roadmap walks you through these decisions in the right order, in plain English.

Your next step:

Don't guess your way through working past 65.

The rules around delaying Part B, creditable coverage, and your Special Enrollment Period are exactly where the costly mistakes happen. The Medicare 2026 Roadmap walks you through these decisions in the right order, in plain English.