The Seven Weeks
I’m not an insurance agent or a financial advisor, and this isn’t advice about your specific plan. Plans, prices and rules vary by where you live. Use this to ask better questions, then confirm the details on Medicare.gov or with a free counselor.
Last week I told you that Medicare open enrollment opened on October 15, and that you were going to look at your drug list anyway. This is the checklist for doing that on purpose.
Here is the timing. Open enrollment began on October 15 and ends December 7. Whatever you choose takes effect January 1. That is about seven weeks. It sounds like plenty. It isn’t, because the thing that costs people money is not the deadline. It is that nothing happens if you do nothing, and your current plan quietly renews with next year’s prices.

What changed for 2027
Four numbers are worth knowing before you open a single letter.
The Part D out-of-pocket cap rises to $2,400, up from $2,100 this year. That is the most you can be asked to pay out of pocket for covered prescriptions in a year. It is still a ceiling most people never touch, but it moved.
The standard Part D deductible rises to $700, up from $615.
The temporary premium subsidy for Part D plans ends at the close of this year. Federal officials have projected only modest premium increases for most people, but “most” is not “you.” Look at your own number.
Medicare-negotiated prices take effect January 1 on 15 more drugs, including Ozempic, Rybelsus and Wegovy. If you take one of them, your cost may change even if your plan doesn’t.
One more number that has not arrived yet: the 2027 Part B premium. Medicare typically releases it in late October or early November. This year’s is $202.90 a month. Don’t make a final call on a Medicare Advantage plan’s “Part B give-back” until you know the real figure.
Nothing happens if you do nothing, and that is exactly the problem.
The letter you probably didn’t open
By September 30, your plan should have mailed you something called the Annual Notice of Change. It is dull and it is the single most useful document you will get this year. It tells you what changes next year to your premium, your copays, your doctor and hospital network, and which of your drugs are still covered and at what tier.
If you can’t find it, call the number on your plan card and ask for another, or find it in your online plan account. Read three things: the drug list, the pharmacy list, and the network.

The ten-minute test that finds the problem
You do not have to compare every plan in America. You have to answer three questions about your current one.
One: are my drugs still covered? Put every prescription, with the dose, into the free Medicare Plan Finder at Medicare.gov. It shows your estimated total cost for the year under each plan, drugs included. This is the step that catches the bad surprise.
Two: are my doctors and my hospital still in network? If you are in a Medicare Advantage plan, call the doctors’ offices you actually use and ask. Don’t trust a website directory alone. Directories are wrong often enough that the call is worth it.
Three: what would a bad year cost? Not a typical year. A bad one. Look at the out-of-pocket maximum, and at what a hospital stay costs per day.
If all three come back fine, you may be done. Most people who do this and find nothing keep their plan, and that is a perfectly good result.

Connect it to last Monday
If you did the brown-bag review, you already have a one-page medication list. Use it. Enter that exact list into Plan Finder. And if you qualify for a free Medication Therapy Management review from your drug plan, do it before you choose, so you are shopping for a shorter list.
Free help that isn’t selling anything
Every state has a State Health Insurance Assistance Program, called SHIP. It is free, it is federally funded, and the counselors don’t earn commissions. You can reach it through Medicare.gov, or by calling 1-800-MEDICARE.
This matters because the next seven weeks are also scam season. Licensed agents can contact you in some situations, and plenty of people who are not agents call too. Here is the rule I would tape to the phone: Medicare will not call you or come to your door to sell you a plan. If a stranger asks for your Medicare number, even one who says they’re calling from Medicare, hang up and call 1-800-MEDICARE yourself. You only need your Medicare number to enroll in a plan you chose. You do not need to give it to someone who contacted you. We’ll spend all of Friday on this.
What to do this week

- Find your Annual Notice of Change. Read the drug list, the pharmacy list and the network.
- Put your medication list into Medicare Plan Finder and look at the total yearly cost, not just the premium.
- Call the doctors you use and confirm they take your plan for 2027.
- Book a free SHIP counselor if your situation is anything but simple.
- Write down December 7, and decide on your own date, before it, to be done. Do not leave this for December 6.
You spent a lifetime picking things carefully. This is one of the few decisions you get to remake every single year. Take one evening.
Go be bold!
Did you find your Annual Notice of Change, and did your drugs make it through? Reply and tell me what you found. I’m collecting the surprises.
Sources
- PBS NewsHour / Associated Press — Medicare open enrollment starts now. These changes will arrive in 2027 — the October 15 to December 7 window, the $2,400 Part D cap, the $700 deductible, the ending premium subsidy and the 15 newly negotiated drugs
- Kiplinger — Your 2027 Medicare Open Enrollment Guide — when the Annual Notice of Change arrives, and when the 2027 Part B premium is typically announced
- KFF — Medicare Advantage in 2026 — the 2026 Part B premium of $202.90 a month
- Michigan DIFS and MDHHS — Tips to help older adults avoid scams during Medicare open enrollment — Medicare will not call or visit, guard your Medicare number, and verify through 1-800-MEDICARE
- Medicare.gov — Medicare Plan Finder — the free tool for comparing total yearly cost, drugs included
- Medicare.gov — Talk to someone — free counseling through your State Health Insurance Assistance Program (SHIP)