Working past 65 in Indiana: when it is safe to delay Part B
Staying on an employer plan can save you a Part B premium, or cost you a lifetime penalty. The answer depends on employer size and who holds the coverage.
Denise OkaforFounder and senior advisor. August 18, 2026, 7 min read
More of our clients are working into their late 60s, and the most common question we hear is whether they need to sign up for Medicare at 65 anyway. The honest answer is sometimes yes and sometimes no, and the rules turn on a few specific details you can confirm in a single phone call with your benefits office.
Rule one: employer size decides who pays first
If your employer has 20 or more employees, your group health plan pays first and Medicare pays second. In that case you can generally delay Part B without a penalty, as long as you stay covered through active employment, yours or your spouse's.
If your employer has fewer than 20 employees, Medicare becomes the primary payer at 65. Your group plan may pay very little, or nothing, for services Medicare would have covered. Small-employer workers usually need to enroll in Part A and Part B on time.
Rule two: COBRA and retiree coverage do not count
The Special Enrollment Period that protects you from Part B penalties only applies to coverage based on current employment. COBRA, retiree health plans and severance coverage do not qualify, even if they came from a large employer.
This catches people every year. Someone retires at 66, elects COBRA for 18 months, and only then applies for Part B. By that point their eight-month Special Enrollment Period has passed, and they face a late penalty and a gap in coverage.
Should you take Part A while still working?
Part A is premium-free for most people, so many workers enroll in it at 65 for secondary hospital coverage. There is one important exception. If you contribute to a Health Savings Account, enrolling in any part of Medicare ends your ability to make new HSA contributions.
Part A enrollment can also be backdated up to six months when you apply after 65. We recommend stopping HSA contributions at least six months before you plan to enroll to avoid tax penalties.
Compare the costs, not just the rules
Even when you can delay Part B, it is not always the cheaper choice. Some employer plans carry high deductibles and payroll deductions for spouse coverage that exceed what Medicare plus a Supplement or Advantage plan would cost.
We build a quick side-by-side for clients in this spot. On one side is your employer plan: payroll premium, deductible, out-of-pocket maximum and drug copays. On the other is Part B, a Supplement or Advantage plan, and Part D. Sometimes the employer plan wins easily. Sometimes Medicare saves several thousand dollars a year.
What to collect before you leave your job
When you are ready to retire or your employer coverage is ending, gather these items at least two months ahead:
- Form CMS-L564, Request for Employment Information, completed by your employer.
- The creditable coverage notice for your employer drug plan, which protects you from the Part D penalty.
- Your coverage end date, since Part B should start the first day of the following month.
- Your most recent tax return, to anticipate any IRMAA surcharge on premiums.
The eight-month clock
Once employment or the group coverage ends, whichever comes first, you have eight months to enroll in Part B without penalty. Your Medigap Open Enrollment Period starts when Part B begins, and you have 63 days to join a Part D or Advantage plan with drug coverage.
Missing those windows can be expensive and hard to undo. If you are working past 65, a 30-minute review with a licensed advisor is one of the most valuable calls you can make.
This guide is general education, not individual advice. Figures are samples; confirm current amounts at Medicare.gov. Not affiliated with or endorsed by the U.S. government or the federal Medicare program.
