Money Guide

Annual Enrollment Period: Your Medicare Coverage Decisions

Enrollment WindowOct 15 – Dec 7
Coverage StartsJan 1
1
Check the drug list

Confirm your formulary before Dec 7, not after.

2
Compare, don't renew

Auto-renewal is rarely the cheapest plan for next year.

3
Use SHIP counseling

Free, unbiased plan review, no sales pitch attached.

4
Leaving Advantage? Check Medigap first

In most states a Medigap plan can turn you down or charge more after your first window. Get a quote before you switch.

Every October, the envelopes start showing up on the kitchen counter, one from Tony's plan and one from mine, and I don't let either one get set aside until I've gone through it line by line. The plans change every single year, whether you asked them to or not, and the only person who's going to notice a prescription that jumped a tier or a premium that crept up eleven dollars is you. This is the whole process, the way I actually do it.

01 · The timeline

How AEP actually works

Same window every year, same four steps. Once you've done it once, it's a Tuesday afternoon, not a project.

Read the Annual Notice of ChangeArrives by late September, lists what's different next year.
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Compare plans, Oct 15 – Dec 7Medicare Plan Finder or a SHIP counselor, either works.
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Switch or stay putEnroll in something new, or do nothing and keep your current plan.
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New coverage beginsTakes effect January 1. On Medicare Advantage? You get one more switch Jan 1 – Mar 31.
02 · Your options

The three coverage paths

Every choice during AEP boils down to one of these three. Tony and I aren't even on the same one, because our situations aren't the same, and that's normal.

Path 1

Original Medicare (Parts A & B)

Any doctor or hospital that takes Medicare, nationwide. No caps on your share of costs unless you pair it with something else.

Path 2

Medicare Advantage (Part C)

Private plans that bundle hospital, medical, and usually drug coverage. Lower premiums often, but you're working inside a network.

Path 3

Medigap + Part D

Original Medicare plus a supplement that covers the gaps, plus a separate drug plan. Higher monthly cost, fewer surprises later.

03 · Where the money moves

What actually changes your costs

People fixate on the premium because it's the number right at the top. It's rarely the biggest number by the end of the year. Ranked by how much it usually moves your total spending.

Drug tier placementHighest impact
Why it matters: a medication moving from tier 2 to tier 3 can add real money every month, and it's the first thing I check, not the last. Two limits help: covered insulin is capped at $35 a month on every plan, and in 2026 your yearly out-of-pocket spending on covered Part D drugs tops out at $2,100. So for Tony, the question is where his other prescriptions landed.
DeductibleHigh impact
Why it matters: the amount you pay before the plan kicks in resets every January 1. A lower premium with a much higher deductible can cost more overall.
Monthly premiumModerate impact
Why it matters: steady and predictable, which is why it gets all the attention. But it's often the smallest piece of the whole picture next to prescriptions and deductibles.
Pharmacy and doctor networkModerate impact
Why it matters: a cheaper plan that drops your regular pharmacy or specialist isn't actually cheaper once you factor in driving across town or paying out of network.
Extra benefitsLower impact
Why it matters: dental, vision, and gym memberships are nice, but they shouldn't be the reason you pick a plan. Get the core coverage right first.
04 · What trips people up

Common AEP mistakes

I've watched people I know make every one of these, myself included, back before I paid attention.

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Letting the plan auto-renew
Premiums, deductibles, and drug lists reset every year. "It worked last year" isn't a guarantee.
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Skipping the drug list check
A medication can move tiers or drop off the formulary entirely without much warning. Check it every single year.
×
Waiting until December 7
SHIP counselors and plan hotlines get booked solid in the last week. Start the first week of the window instead.
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Only comparing the premium
The deductible and drug copays usually add up to more over a year than the monthly number does.
×
Not checking the pharmacy network
A great plan on paper isn't great if it doesn't include the pharmacy you actually use every month.
One more thing

Keep this handy for October

You don't need to memorize any of this. You just need to know where to find it again when the envelopes show up.

AEP dates (Oct 15 – Dec 7) and the Jan 1 coverage start are set by Medicare each year. For plan comparisons or free counseling, medicare.gov and your local State Health Insurance Assistance Program (SHIP) are the official, no-cost resources.