Medicare Advantage

Still Working at 65 in Bear? Know Your Medicare Deadlines

# Still working at 65 in Bear? Here's how Medicare deadlines line up with your job…

BEAR, Del. — If you're turning 65 while still working at a job that offers health insurance, the biggest question usually isn't which Medicare option to pick. It's when — and what happens if you miss a window.

BEAR, Del. — The good news: Bear sits in New Castle County, where there are plenty of Medicare choices when you're ready. For 2026 the county has 36 Medicare Advantage plans offered by 8 carriers with drug coverage built in; the 2027 lineup will be in each plan's ANOC and on Medicare.gov's Plan Finder. But the number of options matters less than getting the timing right. Sign up at the wrong moment and you can face gaps in coverage, lifelong penalties, or both.

Here's how the enrollment windows fit together when you have employer coverage in the picture.

Your first deadline: the Initial Enrollment Period

Everyone gets a 7-month Initial Enrollment Period (IEP) around their 65th birthday. It starts 3 months before the month you turn 65, includes your birthday month, and ends 3 months after.

If you're not working — or your employer coverage doesn't count as "creditable" — this is your window to sign up for Part A, Part B, and a drug plan without penalty. Miss it, and you could pay higher premiums for as long as you have Medicare.

For most people in Bear, Part A is premium-free, so signing up at 65 is an easy call even if you keep working. Part B and Part D are the pieces that require a real decision.

Still working? You may be able to delay Part B

If your employer has 20 or more employees and you're covered by that group health plan, you generally can put off enrolling in Part B without a late penalty. When the job or the coverage ends, you get an 8-month Special Enrollment Period (SEP) to sign up for Part B.

A few timing traps to know about:

• The SEP is 8 months from when the job or coverage ends — whichever comes first. COBRA and retiree coverage do not extend it.
• Smaller employer (under 20 workers)? Medicare usually becomes the primary payer at 65, so delaying Part B can leave you underinsured. Talk to your benefits office before your IEP closes.
• HSA contributions stop once you enroll in any part of Medicare, including premium-free Part A. If you want to keep contributing, coordinate the timing carefully.

Part D and creditable drug coverage

Your employer plan should send you a notice every year telling you whether its drug coverage is "creditable" — meaning at least as good as standard Medicare Part D. Keep those notices.

If your coverage is creditable, you can delay Part D without a penalty and pick up a drug plan later during a 2-month Special Enrollment Period after the employer drug coverage ends. If it isn't creditable and you go more than 63 days without Part D, a late-enrollment penalty will be added to your premium — permanently.

One note on options in the area: Delaware has 10 stand-alone Part D plans for 2026, sold statewide, so if you stay with Original Medicare you can join one of those, or you can get drug coverage bundled inside a Medicare Advantage plan (an MA-PD). That makes the creditable-coverage question especially important to sort out before you leave your job.

The two windows to know after you're enrolled

Once you're in Medicare, two annual windows drive most changes:

• Annual Enrollment Period (AEP): Oct. 15 – Dec. 7. This is when anyone with Medicare can join, switch, or drop a Medicare Advantage or Part D plan for the following year.
• Medicare Advantage Open Enrollment Period: Jan. 1 – March 31. If you're already in a Medicare Advantage plan, you get one chance during these months to switch to a different MA plan or drop back to Original Medicare.

Mark both on your calendar the year you enroll. Plans change every year — premiums, drug lists, and provider networks can all shift — and these windows are your regular chance to react.

2027 program changes worth planning around

A few program-wide numbers may shape when you decide to enroll:

• Part D out-of-pocket cap is $2,100 in 2026 and $2,400 in 2027. Once your covered drug spending hits that amount, you pay nothing more for covered drugs the rest of the year.
• Part D maximum deductible is up to $615 in 2026 and up to $700 in 2027.
• The coverage gap ("donut hole") is gone as of 2025. Part D now has three phases instead of four.
• The Medicare Prescription Payment Plan lets you spread drug costs across the year in monthly installments instead of paying at the pharmacy counter.
• IRMAA surcharges for higher-income enrollees start above $109,000 for a single filer in 2026. If you're still drawing a paycheck, this may affect your Part B and Part D premiums for a year or two.

What to do if you missed a deadline

If you think you missed your IEP or an SEP, don't guess. Call 1-800-MEDICARE, or reach out to Delaware's State Health Insurance Assistance Program (SHIP), called ELDERinfo Delaware, for free one-on-one counseling. They can look at your specific situation, confirm what penalties (if any) apply, and help you find the next enrollment window.