Prepare for Medicare open enrollment with a parent
Organize your parent's medicines, doctors and costs and get a plain-English list of questions before comparing plans on Medicare.gov or with a free counselor.
Estimate: 2–3 hours of reading plan mail, plus a better chance of catching a costly change. (Estimate; results vary.)
- ChatGPT (free)
- Claude (free)
- Medicare.gov Plan Finder (free)
- Your state's free SHIP Medicare counseling (shiphelp.org)
1–2 hours, between October 15 and December 7
Free (free AI tier, Medicare.gov Plan Finder, SHIP counseling)
The problem
Every fall, Medicare open enrollment (October 15 to December 7) brings a mailbox full of plan ads and a confusing Annual Notice of Change. Many families keep the same plan without checking whether medicines or doctors are still covered, or end up on the phone with a salesperson.
Step by step
- 1Gather your parent's current plan name, the Annual Notice of Change letter from that plan (it usually arrives by the end of September), their medication list with doses, and their doctors and pharmacy.
- 2Paste the plan letter text (with member ID and name removed) and the medicine and doctor list into ChatGPT or Claude with the prompt below to get a plain-English summary and questions.
- 3Compare plans on the official Medicare.gov Plan Finder by entering the medicines and pharmacy. It shows estimated yearly drug costs and which plans cover them.
- 4For free, unbiased one-on-one help, contact your state's SHIP (State Health Insurance Assistance Program) counselors through shiphelp.org. They do not sell plans.
- 5Decide with your parent before December 7, and save a copy of anything you enroll in. Never give a Medicare number to someone who calls, texts or emails out of the blue.
Copy-paste prompt
Help me get ready for Medicare open enrollment with my parent. Current plan: [plan name and type, e.g., Medicare Advantage or Part D]. Here is the text of their Annual Notice of Change letter [paste; remove name and member ID]. Their medicines and doses: [list]. Their doctors and pharmacy: [list]. What matters most to them: [low monthly cost / keeping certain doctors / lowest drug costs / travel coverage]. Give: (1) a plain-English summary of what is changing next year in their plan; (2) a checklist of what to look up on the Medicare.gov Plan Finder; (3) 10 questions to ask a SHIP counselor or the plan; (4) warning signs of Medicare scams and pushy sales calls. Do not recommend a specific plan. If something in the letter is unclear, say so instead of guessing.
Tips and watch-outs
- Remove the member ID and Medicare number before pasting plan letters into AI.
- Use Medicare.gov and your state's free SHIP counselors for plan comparisons; AI summaries can miss details.
- Medicare will not call, text or email out of the blue asking for a Medicare number; hang up on anyone who does.
Review AI output before using it. Don’t paste confidential, customer or patient data into tools your company hasn’t approved.
Free · 5 minutes
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