This pack
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All seven steps online and in a downloadable PDF, with a printable checklist and comparison worksheet.
GUIDED PACK · 7 STEPS · REVIEWED SEPTEMBER 2026
Medicare Open Enrollment Prep
Seven guided steps that turn your plan letter, your medicines and your doctors into a clear question list and a side-by-side cost comparison, ready for Medicare's Plan Finder or a free counselor.
It doesn't recommend a plan, sell insurance, or replace a licensed counselor. It helps you prepare. The final choice is yours, made with official information.
- September 2026Read your Annual Notice of Change; contact your plan if it has not arrived.
- October 1, 2026Start checking 2027 plan information.
- October 15–December 7, 2026Medicare Open Enrollment.
- January 1, 2027Coverage from Open Enrollment takes effect.
Why this guide costs $2.
Plans change every year.
Premiums, drug lists, pharmacy networks and doctor networks can all shift for 2027, even if you keep the same plan.
The drug numbers moved.
In 2027, the annual out-of-pocket limit for covered Part D drugs is $2,400. The maximum standard Part D deductible is $700. Premiums and non-covered drugs are not included in that out-of-pocket limit.
The hard part is knowing what to ask.
A guided sequence helps you organize the information and questions you want to bring to Plan Finder or a counselor.
Keep a useful record.
Bring a question list and a comparison worksheet to your next conversation. Check doctor networks and drug coverage before you decide.
SMALL PRICE. PRACTICAL STEPS.
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What’s inside
Use any AI chat you like. Copy a prompt, replace anything in [brackets], paste it in, and keep the conversation going. Each step builds on the last, so stay in the same chat.
STEP 1 · FREE PREVIEW
Read your plan's change letter
Your plan mails an Annual Notice of Change (ANOC) by the end of September. It lists what's different next year. It's long and dense. Type or paste just the "summary of changes" table, with your name and ID removed.
Copy this prompt, then fill in the brackets.
Below is the "summary of changes" section from my Medicare plan's Annual Notice of Change for 2027. I've removed my personal details. Please explain it in plain English: 1. What is changing, in a short list, most important first. 2. Which changes could raise my costs. 3. Anything I should double-check with the plan directly. Don't recommend a plan. Just help me understand this letter. [paste the summary of changes here] Do not recommend a specific plan, product or company. End by reminding me to check important details with Medicare.gov, my plan or a SHIP counselor before acting.
Check before you act: Compare the summary with the original letter, and confirm unclear changes with your plan or a SHIP counselor. AI may miss an exception.
Steps 2–7 are part of this guide.
Get the full guide for $2, or save with a bundle. The remaining prompt text is delivered only after a purchase.
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STEP 2
Build your medicine list
Included in the full pack.
STEP 3
List your doctors and pharmacy
Included in the full pack.
STEP 4
Decide what matters most to you
Included in the full pack.
STEP 5
Make your question list
Included in the full pack.
STEP 6
Compare yearly costs without counting twice
Included in the full pack.
STEP 7
Write your decision summary
Included in the full pack.
Before you act
Use this checklist on paper. For a personal comparison, fill in the blank worksheet below without sending your details to us.
Open the blank comparison worksheet
Write the exact label from Plan Finder beside each number. Ask a counselor about gaps and overlaps before adding them.
| Item to check | Plan A | Plan B | Plan C |
|---|---|---|---|
| Exact plan name / year | ________ | ________ | ________ |
| Estimate label and amount | ________ | ________ | ________ |
| Does it include premiums? | ________ | ________ | ________ |
| Does it include deductibles? | ________ | ________ | ________ |
| Other non-overlapping costs | ________ | ________ | ________ |
| Doctor and drug coverage | ________ | ________ | ________ |
| Excluded or uncertain costs | ________ | ________ | ________ |
| Questions for Medicare or SHIP | ________ | ________ | ________ |
The printout includes the steps you have opened. Your checkmarks are not sent to us.
Official help is free.
- Medicare Plan Finder
Compare 2027 plans with your own drugs and pharmacy.
- SHIP counselors
Free, unbiased, one-on-one Medicare help in every state. They don't sell plans.
- 1-800-MEDICARE (1-800-633-4227)
Available 24 hours a day.
- Extra Help
If your income is limited, you may qualify for help paying drug costs.
- CMS 2027 Part D figures
Official source for the $2,400 out-of-pocket limit and $700 maximum standard deductible.
- Medicare Open Enrollment dates
Confirm enrollment dates and when coverage starts.
- Protect yourself from fraud
Medicare’s guidance on suspicious calls and protecting your information.
Reviewed September 2026 for 2027 coverage. CMS’s 2027 Rate Announcement sets the annual out-of-pocket limit for covered Part D drugs at $2,400 and the maximum standard deductible at $700. The limit excludes premiums and non-covered drugs. Plan costs vary; confirm details with Medicare.gov or your plan. This guide is educational, not insurance, medical or legal advice. It does not recommend or sell insurance. AI can make mistakes; you remain in charge of decisions. Next scheduled review: September 2027.