Medicare 2026

Medicare Advantage or Medigap? Watch These Key Dates

NEW HAVEN, Conn. — Choosing between Original Medicare with a Medigap policy and a Medicare Advantage plan is one of the biggest decisions on the road into Medicare. But the choice is not just about which path fits your life today. It is also about when you make it. Miss a window, and the door to switching later can narrow — or, in the case of Medigap, sometimes close for good.

Here in New Haven, and across New Haven County, the calendar matters as much as the coverage.

The two paths, in one paragraph

Original Medicare (Parts A and B) is the federal program. Because it does not cap your out-of-pocket costs on its own, many people pair it with a standalone Medigap (Medicare Supplement) policy and a separate Part D drug plan. Medicare Advantage (Part C) is a private, all-in-one alternative that bundles hospital, medical, and usually drug coverage, and uses plan networks and rules. Both paths are real Medicare. What separates them, practically, is how you switch between them — and when.

The window that catches people off guard: Medigap

The most important date in this whole conversation is your Medigap Open Enrollment Period. It is a one-time, six-month window that begins the first month you are both 65 or older and enrolled in Medicare Part B. During those six months, insurers must sell you any Medigap policy they offer at their best available rate, no matter your health history.

Once that window closes, federal rules no longer guarantee you a Medigap policy. Insurers in most states can use medical underwriting — meaning they can review your health, charge more, or turn you down. Connecticut is one of a small number of states with additional Medigap protections beyond the federal minimum, but the rules can be technical. The State Health Insurance Assistance Program (called CHOICES in Connecticut) can walk you through what applies to your situation.

The takeaway: if you think you might ever want a Medigap policy, the safest time to get one is during that first six-month window.

The windows for Medicare Advantage and Part D

Medicare Advantage and Part D drug plans work on an annual cycle:

• Annual Enrollment Period (AEP): October 15 – December 7. This is when anyone with Medicare can join, drop, or switch a Medicare Advantage plan or a Part D plan. Changes take effect January 1.
• Medicare Advantage Open Enrollment Period: January 1 – March 31. If you are already in a Medicare Advantage plan on January 1, you get one chance during these three months to switch to a different Advantage plan or drop back to Original Medicare (and pick up a Part D plan). This window is not open to people who are in Original Medicare on January 1.

There is also an Initial Enrollment Period around your 65th birthday — a seven-month window that starts three months before the month you turn 65 and ends three months after. You can pick up Part D or a Medicare Advantage plan then, too.

How the dates interact — and where people slip

The pieces fit together in ways that are easy to miss:

• Starting in Medicare Advantage and later wanting Medigap. Someone who chooses Advantage at 65 and, a few years later, decides they want Original Medicare plus Medigap can generally switch back to Original Medicare during AEP or the Advantage Open Enrollment Period. But buying a Medigap policy after that first six-month window is not guaranteed. That is the trap. You can leave Advantage; you may not always be able to get the Medigap policy you want.
• Delaying Part D. If you go without creditable drug coverage after you are first eligible, a late enrollment penalty can be added to your Part D premium — permanently. The Prescription Payment Plan, a newer option that lets you spread drug costs over the year, does not erase this penalty.
• Assuming AEP fixes everything. AEP lets you change Advantage and Part D plans. It does not, by itself, hand you a Medigap policy.

What is not changing: the program's structure

A few federal figures are worth knowing as you weigh the two paths for the coming year. In 2026, Part D has a $2,100 annual out-of-pocket cap on covered drugs, and the maximum Part D deductible is $615. The old coverage gap, or "donut hole," was eliminated in 2025, so Part D now has three phases. Higher-income beneficiaries — generally those with income above $109,000 as a single filer — pay IRMAA surcharges on Part B and Part D. These rules apply the same way whether your drug coverage comes through a standalone Part D plan or is built into a Medicare Advantage plan.

New Haven County: plenty of choices, same rules

New Haven is in New Haven County, where a range of Medicare Advantage and Part D plans are offered each year by multiple carriers. The exact count changes annually, and Medicare's Plan Finder at medicare.gov is the most current source. But the number of plans on the shelf does not change the deadlines above — those windows are federal and apply the same way in New Haven as anywhere else.

Where to get personal help

Because your health, your prescriptions, and your budget are yours alone, plan choice is a personal decision. Two good, unbiased places to start:

• Medicare.gov — official plan comparisons and rules.
• 1-800-MEDICARE (1-800-633-4227) — 24/7 help line.
• CHOICES, Connecticut's SHIP — free, one-on-one counseling for Medicare beneficiaries and their families.