Medicare Part D

Still Working at 65 in Denver? Avoid Costly Medicare Slip-Ups

DENVER — If you're approaching 65 and still clocking in at work, you're facing one of the trickiest questions in Medicare: sign up now, or wait? The answer depends on the size of your employer, the kind of coverage you have, and a few deadlines that don't bend for anyone.

Getting this right matters. A missed window can mean lifelong late penalties and gaps in coverage. Here's how to think it through.

Start with the size of your employer

The rules hinge on how many people work at your company.

• 20 or more employees: Your job-based plan usually pays first, and Medicare pays second. Many people in this situation delay Part B (and sometimes Part A) without penalty as long as they keep that coverage.
• Fewer than 20 employees: Medicare typically pays first. If you don't enroll in Part B when first eligible, your employer plan may pay very little, leaving you exposed.

If you're not sure which category you fall into, ask your HR or benefits office in writing. This is the single most important question to answer before your 65th birthday.

Part A is usually a "yes"

Most people qualify for premium-free Part A (hospital insurance) because they or a spouse paid Medicare taxes long enough. If that's you, enrolling in Part A at 65 is often a simple step — it can work alongside employer coverage.

One exception: if you contribute to a Health Savings Account (HSA), you cannot keep adding to it once you're enrolled in any part of Medicare, including Part A. If your HSA matters to you, talk with your employer before signing up.

Know your enrollment windows

Three enrollment periods matter most when you're still working:

1. Initial Enrollment Period (IEP): The 7-month window around your 65th birthday. 2. Special Enrollment Period (SEP): If you delay Part B because you have qualifying employer coverage, you generally get up to 8 months after that job or coverage ends to enroll without a late penalty. 3. General Enrollment Period: January 1 – March 31 each year, for people who missed their other windows. This is the fallback — and it can come with penalties.

For prescription drug coverage (Part D), you need "creditable coverage" from your employer to avoid a late enrollment penalty later. Your plan should send you a notice each year telling you whether your drug coverage counts as creditable. Keep those notices.

The most common mistakes to avoid

• Assuming COBRA counts. COBRA is not considered active employer coverage for Medicare purposes. If you're on COBRA at 65, you generally still need to enroll in Part B on time.
• Assuming retiree coverage counts. Same issue — retiree health benefits don't delay your Medicare deadlines.
• Missing the 8-month SEP window after leaving a job. It goes faster than people expect.
• Forgetting Part D. Even if you don't take many prescriptions today, going without creditable drug coverage for 63 days or more can trigger a permanent penalty.

What's new for 2027

A few program-level facts worth knowing as you plan:

• Part D out-of-pocket cap: $2,100 in 2026 and $2,400 in 2027. Once your out-of-pocket drug spending hits that amount, you pay nothing for covered drugs the rest of the year.
• Part D maximum deductible: $615 in 2026 and $700 in 2027.
• The coverage gap ("donut hole") is gone as of 2025. Part D now has three phases instead of four.
• Medicare Prescription Payment Plan: An optional program that lets you spread your out-of-pocket drug costs across the year in monthly payments instead of paying at the pharmacy counter.
• IRMAA: Higher-income enrollees pay a surcharge on Part B and Part D premiums. For single filers in 2026, IRMAA begins above $109,000 in income (based on your tax return from two years earlier).

Denver-area availability

Denver is in Denver County, where Medicare plan choices — including Medicare Advantage and stand-alone Part D plans — are set at the county level by the Centers for Medicare & Medicaid Services (CMS). If you want to see how many plans and carriers serve your county, the plan finder at medicare.gov lets you search by ZIP code. Availability can shift each year, so it's worth checking annually during the Annual Enrollment Period, October 15 – December 7.

If you enroll in a Medicare Advantage plan and change your mind, the Medicare Advantage Open Enrollment Period runs January 1 – March 31, giving you one chance to switch or return to Original Medicare.