Working Past 65? The Hidden Truth About Medicare and Social Security Timing

ACISPosted in Medicare on October 26, 2025 last updated on October 26, 2025

Many people turning 65 aren’t ready to retire — and that’s perfectly fine. But if you’re still working, understanding how Medicare interacts with your employer coverage is essential. Here’s what to know about who pays first, when to enroll, and how to avoid penalties.

Working Past 65? Here’s How Medicare Works When You’re Still Employed

By Allied Comprehensive Insurance Strategies, LLC (ACIS)

Turning 65 doesn’t always mean turning in your office keys. Many Americans continue to work well beyond traditional retirement age — either for enjoyment, financial goals, or to keep their excellent employer benefits.

But one of the most common questions I hear is:

“If I’m still working and have group insurance, do I still need Medicare?”

The short answer: It depends on the size of your employer.

🧩 1️⃣ Who Pays First — Medicare or Your Employer?

This is the key question because it determines whether you should enroll in Medicare now or delay it.

If your employer has 20 or more employees:
- Your employer coverage pays first, and Medicare is secondary.
- You can usually delay Medicare Part B (which carries a monthly premium) and keep your current insurance with no penalty.
- Many people still enroll in Part A (hospital coverage) since it’s premium-free, but it typically pays after your employer plan.
- When you retire or lose coverage, you’ll have an 8-month Special Enrollment Period (SEP) to sign up for Part B and Part D without penalty.
If your employer has fewer than 20 employees:
- Medicare becomes primary, and your group insurance becomes secondary.
- You’ll need to enroll in both Part A and Part B at age 65 to avoid coverage gaps.
- You’ll also want to add prescription drug coverage through either a Part D plan or a Medicare Advantage plan (MAPD) that includes drug coverage.
- Delaying Part B or D in this situation can lead to late-enrollment penalties later on.

💬 2️⃣ How to Verify Employer Size and Coverage

It’s ultimately your responsibility to confirm these details, but your HR or benefits department can provide the answers quickly.

Ask them:

“Does our employer coverage qualify as creditable coverage for Medicare Part B and Part D?”
“How many full-time employees does the company have?”

If you’re working for a small company (fewer than 20 employees), Medicare will almost always become your primary insurance once you turn 65.

💰 3️⃣ What About the Cost of Part B?

If Medicare becomes primary, you’ll pay the standard Part B premium, projected to be about $206.50/month in 2026 (based on the Medicare Trustees’ report).

That amount is in addition to any Part D or Advantage plan premiums you might choose — but remember, your group plan will only cover what’s left after Medicare pays.

🧾 4️⃣ Delaying Social Security?

If you’ve chosen to delay Social Security until age 70 (a smart move for many), you’ll simply pay your Part B premium directly to Medicare instead of having it deducted from your Social Security check.

🧠 5️⃣ The Bottom Line

Continuing to work at 65 can make sense financially and emotionally — but your Medicare decision depends entirely on your employer’s size and coverage type.

20+ employees: You can usually delay Part B and D safely.
Under 20 employees: Enroll in A and B at 65 — and don’t skip drug coverage.

Before making a decision, verify your coverage with HR and get written confirmation. This small step protects you from future penalties and ensures your transition to Medicare goes smoothly when you do retire.

💬 ACIS Perspective

At ACIS, our mission is to make Medicare approachable and transparent — especially for those navigating work and retirement transitions.

If you’re turning 65 and unsure how your employer plan fits into Medicare, let’s review it together. We’ll confirm who pays first, identify any gaps, and ensure your coverage fits both your healthcare and financial goals.

Allied Comprehensive Insurance Strategies, LLC
📞 888-269-4449 | 🌐 coveredbyacis.com
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