First, the scope

What This Window Actually Lets You Do

Medicare's Annual Enrollment Period runs October 15 – December 7 every year, and it only unlocks three specific moves. If you're already enrolled in Medicare, you can use it to:

• Switch which Medicare Part D prescription drug plan you're on
• Switch which Medicare Advantage plan you're on
• Leave Medicare Advantage entirely and move to Traditional Medicare plus a Medigap policy

Already on Original Medicare With a Medigap Policy?

Your real task this fall is on the drug-plan side, not the Medigap side. Part D pricing and drug coverage reset every year, so a plan that worked for your budget last year can look completely different heading into next year — even if nothing about your own health has changed at all.

1. Expect an Annual Notice of Change (ANOC) letter from your current Part D carrier to arrive in early October, spelling out exactly what's different for 2027.
2. Pull together your actual medication list before you compare anything — the right plan depends entirely on what you're actually taking.
3. Use Medicare.gov's own plan-comparison tool against that list, or call and we'll walk through it with you.
4. Whatever you decide, it has to be locked in by December 7th.

One timing trick worth knowing: insurers typically send a rate-increase notice around your Medigap policy's anniversary date. That letter landing in your mailbox is often the natural moment to check whether a lower rate is available elsewhere — ask what your specific state requires before assuming you'd need to requalify.

Already on a Medicare Advantage Plan?

Two different moves are on the table this fall, and they lead to very different outcomes — worth being clear on which one you're actually making before you start comparing plans.

Staying on Medicare Advantage, just switching carriers

Start with your own providers, not the plan's advertised perks. Build your current doctor list and medication list first, then compare candidate plans against that specific list — a plan with a great dental benefit doesn't help much if your cardiologist is out of network. We can run that comparison with you directly.

Leaving Medicare Advantage for Original Medicare + Medigap

This path usually involves medical underwriting to get approved for a Medigap policy, with a few notable exceptions worth checking before you assume the worst:

• In certain states, underwriting typically isn't required to switch Medigap plans at all.
• If your current Advantage plan is the one ending your coverage — a carrier-initiated termination — you get guaranteed-issue rights to specific Medigap plans regardless of your health history.
• Outside those two situations, plan on a short health questionnaire as part of applying.

If none of that applies to you, the safer order is: apply for the Medigap policy first, and only enroll in a standalone Part D plan once that approval comes through — all before December 7th.

Worth remembering either way: Medicare Advantage carries its own separate window every January 1 through March 31 where you can still switch plans or drop Advantage, completely outside of AEP.

Don't Know Which of These Is You?

Skip the guessing — your coverage is on file and easy to pull up in a couple of clicks:

1. Sign in (or set up a free account) at MyMedicare.gov.
2. Open "My Plans" to see exactly what you're currently enrolled in.

From there, jump back to whichever section above matches — or skip the lookup entirely and just call; we can usually sort it out together in a few minutes.

Haven't Enrolled in Medicare Yet? This Isn't Your Deadline

If you're not on Medicare at all, December 7th means nothing for you — AEP only exists for people already enrolled. You're working against a different clock entirely, and which one depends on your situation:

• Approaching 65 for the first time: your own Initial Enrollment Period (IEP) applies, built around your birthday month rather than the fall calendar.
• Coming off an employer's health plan later in life: a Special Enrollment Period (SEP) applies instead, timed to when that employer coverage actually ends.

This guide is for general educational purposes and isn't a statement of your personal coverage. Enrollment rules vary by state and individual circumstance — reach out directly for guidance specific to your situation.