Medicare 2026

Working Past 65 in Mililani? Don't Miss This Medicare Window

# Working Past 65 in Mililani? Don't Miss This Medicare…

MILILANI, Hawaii — More Hawaii residents are staying on the job well into their 60s, and that means a growing number of workers here are trying to figure out how Medicare fits with the health plan they already have through work. The rules are not always obvious, and the wrong move can trigger a lifetime late-enrollment penalty. Here is what Mililani workers and their spouses should know before that 65th birthday arrives.

Who pays first depends on the size of your employer

Medicare uses "coordination of benefits" rules to decide which coverage pays first when you have both Medicare and a group health plan.

If your employer (or your spouse's employer, if you are covered through them) has 20 or more employees, the group plan is the primary payer and Medicare is secondary. In this case, many workers choose to delay Part B to avoid paying a premium for coverage they do not yet need.

If the employer has fewer than 20 employees, Medicare is usually primary. That means you generally need to enroll in both Part A and Part B at 65, because the group plan will only pay after Medicare pays its share. Skipping Part B in that situation can leave you with big bills.

Rules can differ for retiree coverage, COBRA, TRICARE, and VA benefits, so it is worth confirming your situation before making a decision.

Should you take Part A at 65?

For most people, yes. Part A is premium-free if you or your spouse paid Medicare taxes for at least 10 years, and it can help pick up some hospital costs your employer plan does not cover.

One caveat: if you contribute to a Health Savings Account (HSA) through work, enrolling in any part of Medicare — including Part A — stops you from making new HSA contributions. Some workers near Schofield Barracks or commuting into Honolulu who rely on HSAs choose to delay all of Medicare until they retire. Talk with your benefits office before you decide.

The 8-month window after you leave the job

When your job-based coverage ends — whether you retire, get laid off, or lose the group plan — you get a Special Enrollment Period (SEP) of up to 8 months to sign up for Part B without a late penalty. COBRA does not extend this window, even though it can feel like active coverage. Waiting past the 8 months can mean a Part B penalty of 10% for every full 12 months you should have had it, added to your premium for as long as you have Medicare.

There is a similar 63-day window to pick up a Part D drug plan or a Medicare Advantage plan with drug coverage after your employer coverage ends.

Don't overlook Part D and "creditable" drug coverage

If your employer plan includes prescription drugs, ask your HR office or benefits administrator each year for a "creditable coverage" notice. Creditable means the drug coverage is at least as good as standard Medicare Part D.

• If it is creditable, you can delay Part D with no penalty.
• If it is not creditable and you go without Part D for 63 days or more, you may owe a permanent late-enrollment penalty when you eventually sign up.

The Part D out-of-pocket cap is $2,100 in 2026 and $2,400 in 2027, and the maximum deductible is $615 in 2026 and $700 in 2027. The old coverage gap or "donut hole" is gone, replaced by three simpler payment phases. Medicare also offers a Prescription Payment Plan that lets you spread your drug costs across the year in monthly amounts instead of paying large bills at the pharmacy counter.

What Mililani residents can expect locally

Mililani is in Honolulu County, where Medicare Advantage and stand-alone Part D plan availability is set at the county level. If and when you decide to leave employer coverage, you will have a range of plan options to compare through Medicare's official plan finder. The Annual Enrollment Period runs October 15 through December 7 each year, and the Medicare Advantage Open Enrollment Period runs January 1 through March 31 for people already in an Advantage plan.

Higher-income workers should also know about IRMAA — an income-related surcharge on Part B and Part D premiums that begins above $109,000 in income for a single filer in 2026 (higher for joint filers). It is based on your tax return from two years earlier, so a big final working year can affect your premiums later.

Common mistakes to avoid

• Assuming COBRA counts as active coverage for Medicare purposes — it does not.
• Signing up for Part A while still contributing to an HSA.
• Missing the 8-month Part B window after leaving your job.
• Not getting the annual creditable-coverage letter from your employer plan.
• Waiting until the last minute — Social Security enrollment for Part B is not instant.