Medicare Open Enrollment Checklist: Your 30-Minute Prep
13 October 2026 · RetiredPerks editorial team
Medicare open enrollment starts this Thursday, October 15, and runs through Monday, December 7. That sounds like a project. It is not, at least not yet.
The people who have an easy time with open enrollment are not the ones who read every plan brochure. They are the ones who sit down for one shot of prep before the window opens, so that when they do compare plans, everything they need is already on one sheet of paper.
That prep takes about 30 minutes at the kitchen table. Here is the whole thing, timed. Grab a notepad and a pen, and let’s go.
Minutes 0 to 5: Find your cards
Start with the wallet, the junk drawer, or wherever cards live in your house. You are looking for two things.
First, your red, white, and blue Medicare card. Copy the Medicare Number onto your notepad exactly as it appears.
Second, any plan cards you carry now: a Medicare Advantage card, a Part D drug plan card, or a Medigap card. Write down the plan name and member ID from each one.
That is it. If a card is missing, do not panic and do not call anyone yet. You can see your coverage by logging in at Medicare.gov, and you can request a replacement card there too. Just note “need replacement card” and keep moving.
Minutes 5 to 15: Write your medication list
This is the ten minutes that saves the most money, so give it the full ten.
Go to the medicine cabinet and line up the bottles. For every prescription you take, copy three things straight off the label:
- The drug name, spelled the way the bottle spells it
- The dosage (for example, 20 mg)
- How often you take it
Do not work from memory. Plans cover specific drugs at specific dosages, and “the little white one for blood pressure” will not get you an accurate price when you compare plans. The bottle has the exact answer, so use it.
Include inhalers, insulin, eye drops, and anything you refill regularly. If a spouse is doing this too, make two separate lists. Each person’s plan is priced against their own medications.
Minutes 15 to 20: List your doctors and your pharmacy
Under the medication list, write down:
- Your primary care doctor
- Every specialist you have seen in the past year, even once
- The hospital or health system you would want if something serious happened
- The pharmacy you actually use, by name and location
Networks change every year. A plan that looks cheaper on paper can cost you more if it pushes your cardiologist out of network or treats your corner pharmacy as non-preferred. With this list in hand, checking networks takes minutes instead of guesswork.
Minutes 20 to 25: Find the ANOC letter and circle what changed
If you have a Medicare Advantage or Part D plan, your insurer mailed you an Annual Notice of Change, usually called the ANOC, and it should have arrived by September 30. It may be in the mail pile you have been meaning to sort. This is the most ignored envelope in America, and it is the one that matters most.
Find it, and with a pen, circle anything that changes for next year:
- The monthly premium
- The deductible
- Copays for doctor visits and hospital stays
- Your drugs: any that moved to a higher tier, added restrictions, or left the formulary
- Any doctors or pharmacies leaving the network
Your plan is allowed to change all of this every single year, and if you do nothing, you are automatically renewed into the changed version. The circles on that letter are your shopping list. If nothing meaningful changed and your plan still fits, that is a fine outcome too. Now you know it instead of hoping it.
If you cannot find the ANOC, call the number on your plan card and ask them to resend it, or view plan materials in your online account.
Minutes 25 to 30: Note what you spent out of pocket this year
Last five minutes. Rough numbers are fine.
Jot down roughly what this year cost you beyond premiums: copays at the doctor, what you paid at the pharmacy counter, any surprise bills. You do not need receipts or a spreadsheet. “About $40 a month at the pharmacy, plus that $300 specialist bill” is plenty.
This number is your benchmark. When you compare plans, you are not comparing premiums in a vacuum. You are asking one practical question: would this plan have cost me less for the year I actually had? That framing catches the plan with the low premium and the high everything else.
Done. Put the notepad somewhere you will find it Thursday.
What can wait (which is almost everything)
Here is what you do not need to do this week, and it is a long list.
You do not need to pick a plan on day one. There is no discount, no priority, and no advantage for enrolling October 15. Nothing you choose takes effect until January 1, whether you enroll on the first day or the last.
You do not need to fear the deadline yet. The window is nearly eight weeks long and closes Monday, December 7. If you make a change and then find something better before December 7, your last choice is the one that counts.
That said, shopping in late October beats shopping in early December. The closer the deadline gets, the longer the hold times at plans and at 1-800-MEDICARE, and the fewer appointment slots your local counselors have open. Early is calmer, not because you have to be, but because it is nicer.
You also do not need to respond to the mailers, calls, and TV ads that are about to ramp up. Legitimate help does not cold call you, and no one from Medicare calls to ask for your Medicare Number. If you want a refresher before comparing, our plain English guide to the difference between Original Medicare and Medicare Advantage is a good place to start.
Where to get free help
Two sources are free, legitimate, and have no sales angle.
Your State Health Insurance Assistance Program (SHIP) offers free, unbiased, one-on-one Medicare counseling in every state. Counselors are not paid by insurance companies and sell nothing. Find your local program at shiphelp.org or call 1-877-839-2675.
Medicare itself is at 1-800-MEDICARE (1-800-633-4227), open 24 hours a day, 7 days a week, and the plan comparison tool at Medicare.gov will use that medication list you just wrote.
One more practical note: while you are reviewing what insurance costs you, the insurance section of our perks page lists current discounts our readers use in this category.
Thirty minutes, one notepad, and you are ready before the window even opens. Subscribe to Retired Perks and we will be in your inbox Thursday morning with day-one coverage of open enrollment, plus what we are seeing in this year’s plans.