Medicare 2026

Working past 65 in Hilo? How to decide when Medicare should start

HILO, Hawaii — Turning 65 while still on the job is more common than it used to be, and it raises a fair question for a lot of Big Island workers: do I have to sign up for Medicare right now, or can I stick with the plan from work?

Medicare 2027Hilo, HI

The short answer is that it depends on the size of your employer, what kind of coverage you have, and how the two programs are supposed to work together. Getting the order right matters, because a missed deadline can mean a lifetime late penalty or a gap in coverage.

The 20-employee rule sets the order

Medicare uses a "primary payer/secondary payer" system when you have two kinds of coverage. Which one pays first depends on how many people work at your employer.

If your employer has 20 or more employees, your group health plan pays first and Medicare pays second. You can usually delay Part B without a penalty as long as you keep that active coverage.

If your employer has fewer than 20 employees, Medicare generally pays first and the group plan pays second. In that case, you often need to sign up for Part A and Part B at 65, because your employer plan may not pay much until Medicare has paid its share. Check with your HR office before you decide — do not guess.

Part A is usually a yes; Part B is the real decision

Most people qualify for premium-free Part A because they or a spouse paid Medicare taxes for at least 10 years. Since it costs nothing extra, many workers sign up for Part A at 65 even while still on the job.

There is one big exception: if you contribute to a Health Savings Account (HSA), you must stop HSA contributions once any part of Medicare starts, including Part A. If keeping your HSA matters to you, you may want to delay all of Medicare, including Part A, until you stop working.

Part B has a monthly premium, so this is where the real math happens. If your employer coverage is solid and your company has 20 or more workers, delaying Part B is often reasonable. If not, signing up on time protects you from penalties and gaps.

The 8-month window after work ends

When your job or your employer coverage ends — whichever comes first — you get a Special Enrollment Period of 8 months to sign up for Part B without a late penalty. This is a Medicare rule, not an employer rule.

One trap to know about: COBRA and retiree coverage do not count as active employer coverage for this purpose. The 8-month clock starts when your active job-based coverage ends, not when COBRA runs out. Waiting to sign up until COBRA ends is one of the most common — and most expensive — mistakes people make.

Part D and prescription drugs

If your employer plan includes drug coverage that Medicare considers "creditable" (at least as good as a standard Part D plan), you can delay Part D without a penalty. Your employer or plan administrator is required to send you a creditable coverage notice each year. Save it. You will need it when you eventually enroll in Part D.

For 2026, Part D has some helpful updates worth knowing about even if you delay:

• The out-of-pocket cap is $2,100 in 2026 and $2,400 in 2027.
• The maximum deductible is $615 in 2026 and $700 in 2027.
• The old "donut hole" is gone; there are now three coverage phases.
• The Medicare Prescription Payment Plan lets you spread drug costs across the year in monthly amounts.

Higher earners should also know about IRMAA — an income-based surcharge on Part B and Part D that kicks in above $109,000 for a single filer in 2026 (higher for joint filers).

What Hilo workers can do locally

Hilo is in Hawaii County, where Medicare plan availability is set at the county level. If and when you do enroll, your options — Original Medicare with or without a Medigap plan and a stand-alone Part D plan, or a Medicare Advantage plan — depend on what is offered in Hawaii County.

Two dates to keep in mind once you are enrolled:

• Annual Enrollment Period: October 15 – December 7.
• Medicare Advantage Open Enrollment: January 1 – March 31.

For personalized help, Hawaii has a State Health Insurance Assistance Program (SHIP) that offers free, unbiased counseling. That is usually the best first call before making a change.