Medicare Open Enrollment Checklist: What I'd Check by Dec 7

A while back I sat down with an ER bill for my mother. It looked like every hospital bill I've ever seen, a column of codes and a total at the bottom that nobody is supposed to question. I questioned it. The same $340 charge was on there twice. Nobody was hiding it. Nobody was looking, either.

Medicare open enrollment works the same way. From October 15 to December 7, you can change your Medicare Advantage or Part D drug plan for 2027, and most of what you need to know is already in a letter your plan mailed you, the Annual Notice of Change. My Medicare open enrollment checklist is short: find that letter, check every prescription and every doctor against it, add up a full year of costs instead of the monthly premium, and compare before December 7. If you do nothing, your plan usually rolls you into its 2027 version, changes and all.

I'm 57, so I'm not on Medicare yet. But I spent October reading the comments under my Social Security video, and the same idea kept showing up in different words. One person wrote, "Medicare takes the cola every year." Another wrote, "The part D prescription plan is going up quite a bit so many will not see a raise." I did the raise math in my post on the 2027 COLA after Medicare. I can't do a thing about the Part B premium. The plan you pick for next year is the one piece of this you still control, and it's decided by December 7.

The letter that matters this month

If you're in a Medicare Advantage plan or a Part D drug plan, your plan was supposed to send your Annual Notice of Change by September 30, according to the State Health Insurance Assistance Programs. It doesn't look exciting. It might be under the grocery flyers right now.

That letter tells you what changes on January 1. The premium. The deductible. Your copays. Which drugs are covered and at what tier. If you're in Medicare Advantage, which doctors and hospitals are in the network. Can't find it? Call the member number on your plan card and ask them to mail another one.

The headlines this fall sound calm. CMS says the average Medicare Advantage premium drops from $14.37 a month in 2026 to $12 in 2027, and the average stand-alone Part D premium goes from $35.09 to $36 (CMS, September 28, 2026). Averages are nice. Nobody pays the average. CMS also says about eight in 10 people in Medicare Advantage can stay in their current plan for 2027 at the same or a lower premium. I always flip numbers like that around. Two in 10 can't.

Drug costs moved too. Medicare.gov lists the 2027 Part D deductible at up to $700, up from $615, and the yearly cap on what you pay out of pocket for covered drugs at $2,400, up from $2,100. Here in Florida, the CMS state fact sheet lists 11 stand-alone drug plans for 2027 and says about 53% of people in one can find a plan with a lower premium than they paid in 2026. That cheaper premium doesn't come find you. You have to go look.

My Medicare open enrollment checklist

This is what I'd do, in this order, with the letter and every pill bottle in the house lined up on the counter.

1. Find the Annual Notice of Change. Read the first page for the premium and deductible, then go straight to the drug section.
2. Check every prescription against the 2027 drug list, including the ones you only fill a few times a year. Is it still covered? Did it move to a higher tier? Does it need approval first now?
3. Check your pharmacy. A pharmacy that was preferred this year can be standard next year, and your copay moves with it.
4. If you're in Medicare Advantage, call every doctor and specialist you care about and ask one question: "Will you be in network with this plan in 2027?" Online directories aren't always current.
5. Do the full-year math in the next section.
6. Compare plans at Medicare.gov with your real drug list and your real pharmacy, or call 1-800-MEDICARE, which CMS says is open 24 hours a day, seven days a week.
7. Write down what you decided and why, and keep it with the letter.

Medicare is one leak in the budget. If you want my list of 25 other places money slips out after 50, with a printable checklist, grab the free Over-50 Money Stretcher.

Do the whole-year math

This is where people get burned. A $0 premium feels like a win, and sometimes it is. Sometimes it's a big deductible and high copays wearing a nice outfit.

Round numbers I made up, so you can see how it works. Plan A has a $0 premium and a $700 deductible. Plan B costs $36 a month with no deductible. That's $432 a year for Plan B. If your prescriptions would eat that whole deductible, Plan A costs you $700 before it pays much of anything, and Plan B costs you $432 plus your copays. The cheap plan isn't always the cheap plan.

So the only number I trust is the year: twelve months of premium, plus the deductible, plus what each drug will cost you over the whole year. The plan comparison at Medicare.gov estimates that drug cost for you once you type in your prescriptions and your pharmacy. Use it. And remember that the $2,400 cap covers what you pay for covered Part D drugs. Your premiums don't count toward it.

I wrote a whole post about how I use AI to find hidden savings after 50, and prescriptions were one of the biggest leaks. Your letter is where that leak shows up first.

Should you switch or stay put?

My honest opinion: everybody should look, and plenty of people should then stay right where they are. Switching to save $3 a month isn't worth learning a new drug list and a new pharmacy routine. Switching because a drug you take every day jumped to a tier that costs you real money every month? That's worth an afternoon.

One warning I'd give any friend. If you're thinking about leaving Medicare Advantage for Original Medicare, talk to a free counselor before you do it. In most states, outside your first enrollment window, a Medigap supplement company can turn you down or charge you more because of your health. That's a choice you can't always undo in January.

SHIP counselors are government funded and give unbiased Medicare counseling at no cost. Find yours at 877-839-2675. In Florida, the program is called SHINE. And if someone calls you out of the blue offering to "review your Medicare benefits," hang up. Your plan already sent the letter.

What that ER bill taught me

I'm no genius with medical bills. I caught that $340 because I read the thing line by line and asked one question out loud: why is this on here twice? It's the same habit I wrote about in my post on retirement fear after 50. You go looking for the leaks, one line at a time.

Your Annual Notice of Change deserves the same twenty minutes. Pour the coffee and read it like it owes you money. Some years it does.

If you want the rest of the list, the 25 places I look for money after 50 plus a printable checklist, get the free Over-50 Money Stretcher and work through it the same week you read your letter.

I'm not a licensed insurance agent, and this isn't financial or medical advice. Numbers are from CMS and Medicare.gov as of October 2026, so check your own plan's letter for yours.

Questions I hear about Medicare open enrollment

When is Medicare open enrollment for 2027 coverage?

October 15 through December 7, 2026, and whatever you pick starts January 1, 2027. If you're in Medicare Advantage, you get one more chance to switch plans from January 1 to March 31, but I wouldn't count on it.

What happens if I don't do anything?

If your plan is still offered next year, you're usually renewed into its 2027 version automatically, with whatever changed. If your plan is ending, it has to tell you in writing, and you'll get time to pick a new one. Doing nothing is still a choice.

What is the Part D out-of-pocket cap for 2027?

Medicare.gov lists it at $2,400 for covered drugs, up from $2,100 in 2026. The deductible can be as high as $700. Premiums don't count toward the cap, so add those on top.

Where can I get free, unbiased help?

Call 1-800-MEDICARE any time, day or night, or find your local SHIP counselor at 877-839-2675. They don't sell plans. In Florida, look for SHINE.