Medicare 2026

Medicare's Dec. 7 Deadline in Milwaukee: What to Do Now

MILWAUKEE — The clock is ticking for people with Medicare in Milwaukee. The Annual Enrollment Period runs from October 15 through December 7, and it is the main window each year to review your coverage, switch plans, or make changes that take effect January 1, 2027.

This fall, the stakes feel a little different. The Part D out-of-pocket cap moves from $2,100 in 2026 to $2,400 in 2027, and drug plans across the country have been reshuffling premiums, formularies, and pharmacy networks. That means the plan that fits you this year may not fit the same way in 2027 — even if you do not change a thing.

What you can actually do between now and December 7

The Annual Enrollment Period (AEP) is broader than many people realize. During this window, you can:

• Switch from Original Medicare (Parts A and B) to a Medicare Advantage plan, or the other way around.
• Change from one Medicare Advantage plan to another.
• Join, drop, or switch a stand-alone Part D prescription drug plan.
• Sign up for Part D for the first time if you missed your initial window (a late-enrollment penalty may apply).

Whatever you pick during AEP becomes your coverage on January 1, 2027. If you do nothing, you generally stay in your current plan — but that plan's 2027 costs, drug list, and provider network may not match 2026.

Why this fall deserves a closer look

Two big Part D changes are worth understanding before you decide:

• The Part D out-of-pocket cap. Once your out-of-pocket spending on covered Part D drugs hits the annual cap — $2,100 in 2026 and $2,400 in 2027 — you pay nothing for covered drugs the rest of that year. The old "donut hole" coverage gap is gone; Part D now has three phases (deductible, initial coverage, catastrophic).
• The Medicare Prescription Payment Plan. This optional program lets you spread your out-of-pocket drug costs across the calendar year in monthly payments instead of paying all at once at the pharmacy counter. You have to opt in through your drug plan.

Higher-income enrollees should also know that IRMAA surcharges on Part B and Part D premiums begin above $109,000 in income for a single filer in 2026.

What's available in the Milwaukee area

Milwaukee is in Milwaukee County, and plan availability is set at the county level. For 2027, Milwaukee County has 40 Medicare Advantage plans from 7 carriers, down from 52 plans in 2026 (same 7 carriers): 34 plans are continuing, 6 are new, 6 are not returning, and 12 have been renamed. When you shop on Medicare's Plan Finder, you'll see the full list of Medicare Advantage plans and stand-alone Part D plans offered in Milwaukee County for 2027, along with each plan's premiums, drug list, pharmacy network, and Star Rating.

Star Ratings are CMS's 1-to-5 quality score for Medicare Advantage and Part D plans. They are a useful data point — not a recommendation — and they sit alongside other things you'll want to weigh, like whether your doctors and pharmacies are in-network and whether your specific medications are covered.

A simple checklist before December 7

1. Read your plan's Annual Notice of Change (ANOC), which was mailed in September. It spells out what is changing for 2027 — and in Milwaukee County, 19 continuing plans have changed something in their terms. 2. Make a list of your current medications, doses, and preferred pharmacies. 3. Confirm your doctors and any specialists you see are in-network for the plan you're considering. 4. Compare plans at medicare.gov/plan-compare using your ZIP code and drug list. 5. If something is unclear, call for help before December 7 — not after.

Where to get unbiased help in Milwaukee

You do not have to figure this out alone, and you do not have to talk to a sales agent to get answers.

• Medicare.gov — the official Plan Finder and enrollment tool.
• 1-800-MEDICARE (1-800-633-4227) — 24/7, free.
• Wisconsin SHIP (State Health Insurance Assistance Program) — free, one-on-one counseling from trained volunteers who do not sell insurance. In Milwaukee County, you can reach a SHIP counselor through the Aging & Disability Resource Center (ADRC) of Milwaukee County.