Medicare Enrollment for People Still Working

Q: Does my spouse’s employer plan let me delay Medicare?

Yes—if it’s active employer coverage and creditable for hospital and drug benefits. Verify this with the plan administrator.

Q: Can I contribute to an HSA if I enroll in Part A only?

No. Enrollment in any part of Medicare (including Part A) disqualifies you from making new HSA contributions.

Medicare Enrollment for People Still Working

Still Working at 65? Build Your Medicare Game Plan

We’ll confirm if you can safely delay Part B and Part D, coordinate with your employer plan, and map out penalty-free steps.

Explore Medicare Services Call 800-533-5969

Medicare enrollment for people still working doesn’t have to be confusing. The right path hinges on employer size, whether your current plan is creditable for Part B and Part D, and the month you actually retire. At Diversified Insurance Brokers, we build a simple timeline so you keep coverage, avoid late enrollment penalties, and transition smoothly when the time comes.

Employer Size: The First Decision Point

20+ employees vs. fewer than 20—why it matters at 65

If your employer (or your working spouse’s employer) has 20+ employees, the group health plan is usually primary. Many people in this situation can delay Part B and Part D without penalty while still working. If the employer has fewer than 20 employees, Medicare generally becomes primary at 65 and you should enroll in Part B on time to avoid denied claims and penalties. For context and common pitfalls, see Medicare enrollment mistakes to avoid and how Medicare and Social Security work together.

What Counts as “Creditable Coverage” While You’re Working

Active employment coverage is the key

To delay Medicare without penalties, you need active employer coverage that’s creditable for hospital (A), medical (B), and prescription drugs (D). Large-group plans (20+) typically meet this bar; small-group plans often do not. Also note that COBRA and retiree coverage aren’t “active employment” coverage for timing rules, and Marketplace/ACA plans aren’t creditable once you’re Medicare-eligible. When you’re ready to transition, compare Medicare Advantage vs. Medigap, and if you favor Medigap, review Plan G vs. Plan N.

HSA Timing & the 6-Month Look-Back

How Part A affects contributions

Once you enroll in any part of Medicare (even Part A), you can’t contribute to an HSA. Because Part A can be retroactive up to six months, many people stop HSA contributions six months before their intended Medicare start date. If you’re coordinating with Social Security, use our Social Security filing checklist to avoid inadvertent contributions.

COBRA & Retiree Coverage: Helpful, But Watch the Traps

Why relying on them can trigger penalties

COBRA and retiree coverage may help with cost-sharing, but they don’t protect you from Part B or Part D penalties. If you elect COBRA at 65 without Part B, claims can be denied and penalties accrue. Before you act, review our penalty guide: How to Avoid Medicare Late Enrollment Penalties.

Simple Pre-Retirement Timeline

What to do—and when to do it

6–9 months before retirement: Confirm employer size and creditable status for both medical and drug coverage. Decide whether your landing spot is Medicare Advantage or Medigap plus Part D.

2–3 months before retirement: File for Parts A/B (if needed). Compare Medigap Plan G vs. Plan N or review Advantage options with dental/vision benefits.

On/after your retirement date: Use your 8-month Special Enrollment Period for Part B. Add drug coverage immediately (stand-alone Part D with Medigap or MA-PD) to prevent penalties.

Choosing Coverage When You Do Retire

Medigap vs. Medicare Advantage—how to decide

Medigap offers predictable costs and broad provider access—great for frequent travelers and snowbirds. If you lean Medigap, compare Plan G vs. Plan N to balance premium and copays. Medicare Advantage may offer lower premiums with extras like dental and vision, fitness, and care coordination. Start with our overview of the best-rated Medicare Advantage companies and price-check plans using the calculator below.

Real-World Working Scenarios

How the rules apply in practice

Large employer (you): Keep the group plan, delay Part B and Part D, then use the SEP at retirement to add Medicare without penalties—compare Advantage vs. Medigap based on travel, networks, and budget.

Small employer (you): Enroll in Part A and Part B at 65; choose either Medigap (see G vs. N) plus Part D, or a competitive Advantage plan with Rx.

Covered by a working spouse: Confirm the spouse’s employer has 20+ employees and that the plan is creditable. If yes, you can usually delay Part B and Part D. If not, enroll at 65 to avoid gaps and penalties.

Compare Plans & Costs in Minutes

Use our Medicare calculator to see options in your ZIP code

Questions now? Call 800-533-5969

Lock In a Penalty-Free Medicare Start

Book a free review to confirm creditable coverage and exact enrollment dates—and compare Medigap vs. Advantage costs side-by-side.

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Related Medicare Pages

Medicare Enrollment for People Still Working: FAQ

Do I have to enroll in Medicare at 65 if I’m still working?

If your employer has 20+ employees, you can usually delay Part B and Part D without penalty. With fewer than 20 employees, enroll at 65 because Medicare is typically primary.

Does my spouse’s employer plan let me delay Medicare?

Yes—if it’s active employer coverage and creditable for hospital and drug benefits. Verify this with the plan administrator.

Can I keep COBRA instead of signing up for Medicare?

No. COBRA and retiree coverage aren’t considered active coverage for delaying Medicare. Enroll in Medicare to avoid penalties.

What is the Special Enrollment Period (SEP) when I retire?

You have 8 months after employment or group coverage ends (whichever is first) to enroll in Part B without penalty. Enroll in drug coverage right away to avoid Part D penalties.

Can I contribute to an HSA if I enroll in Part A only?

No. Enrollment in any part of Medicare (including Part A) disqualifies you from making new HSA contributions.

Should I choose Medigap or Medicare Advantage when I retire?

Medigap offers broader provider access and predictable costs; Medicare Advantage bundles extras like dental/vision and may have lower premiums. We’ll compare both for your situation.