Medicare 2026

Still on the Job in Richmond? How to Time Medicare Right

If you're approaching 65 and still working at a job in Richmond — whether at a refinery, a school district, Kaiser, or a small business downtown — you may be wondering whether you need to sign up for Medicare right away. The honest answer: it depends on the size of your employer and the kind of coverage you have. Getting the timing right can spare you from late-enrollment penalties and gaps in coverage down the road.

Coordinating Medicare with your Richmond employer plan

Start with the size of your employer

The single most important question is how many people work for your employer. Under Medicare's rules, if your employer has 20 or more employees, its group health plan usually pays first and Medicare pays second. That means you can generally delay Part B (which has a monthly premium) until you retire or lose that coverage, without owing a late penalty later.

If your employer has fewer than 20 employees, Medicare typically becomes the primary payer at 65. In that case, if you don't enroll in Part B when you're first eligible, your employer plan may pay very little — leaving you exposed to big bills. Ask your HR or benefits office in writing which payer is primary once you turn 65.

What about Part A?

Part A (hospital insurance) is premium-free for most people who have worked and paid Medicare taxes for at least 10 years. Because there's usually no cost, many people enroll in Part A at 65 even if they keep their employer coverage.

One important exception: if you contribute to a Health Savings Account (HSA), you and your employer must stop contributing once you enroll in any part of Medicare, including Part A. If your HSA is valuable to you, talk with your benefits team before signing up.

The Special Enrollment Period when you retire

When you eventually leave your job or lose employer coverage, Medicare gives you an 8-month Special Enrollment Period to sign up for Part B without a late penalty. This window starts the month after your employment or your group coverage ends, whichever comes first.

A common mistake: assuming COBRA or retiree coverage counts as "current" employer coverage. It does not. If you're on COBRA at 65, you still need to enroll in Part B on time to avoid a penalty.

What about drug coverage?

If your employer plan includes prescription 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 plan should send you a creditable coverage notice each year — save it.

When you do enroll, Medicare drug coverage has some notable features to know about:

• A Part D annual out-of-pocket cap of $2,100 in 2026 and $2,400 in 2027.
• A maximum Part D deductible of $615 in 2026 and $700 in 2027.
• The old coverage gap ("donut hole") has been eliminated as of 2025.
• The Medicare Prescription Payment Plan lets you spread drug costs across the year in monthly payments.

Local context for Richmond workers

Richmond is in Contra Costa County, where retirees have a range of Medicare Advantage and stand-alone Part D options to choose from once they're ready. You don't need to pick a plan the day you turn 65 if you have solid employer coverage — but it's worth reviewing what's available in the county before your job coverage ends.

The main Medicare enrollment dates to keep on your radar:

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

Also worth noting: higher earners may pay an IRMAA surcharge on top of standard Part B and Part D premiums. For 2026, that surcharge kicks in above $109,000 in income for a single filer (based on your tax return from two years earlier).