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Use ChatGPT or Gemini for real-life paperwork. Calmly. Safely.
Short, plain-English steps for letters, bills, phone calls and strange messages. Copy a prompt, ask the AI, then check its answer yourself.
Ask it.
Copy our ready-made prompt into ChatGPT or Gemini.
Check it.
Hold the answer up against the paper itself.
Act on it.
Call, reply or pay only once the facts match.
In a Medicare plan? Open Enrollment ends Dec 7.
Your plan's yearly notice shows what changes in January. Compare it with AI, then check each change yourself.
Guide 9: Read your plan notice →Guide 8: Check the AI's answer
We are a small, independent site. We are not part of Medicare or the government.
Pick a guide
Each one takes about 5 minutes and works with the free versions of ChatGPT and Gemini.
Understand a Confusing Letter with AI
Know what a hard letter means and what to do next.
Get Ready for a Phone Call with AI
Walk into a call with your questions ready.
Write a Calm Reply with AI
Send a clear, polite reply without the stress.
Plan a Week of Easy Meals with AI
A week of easy meals and one shopping list.
Spot a Scam Message with AI
Get a calm second opinion on a strange message.
Understand a Medical Bill or EOB Before You Pay
See if your medical bill matches your insurance.
Read a Car or Home Insurance Renewal Notice Before You Renew
Spot what changed in your renewal before you pay.
Check an AI Answer Before You Act on It
Catch AI mistakes before they cost you.
Read Your Medicare Plan's Annual Notice of Change (ANOC)
See what your Medicare plan changes next year.
Plan a Holiday Get-Together with AI
Plan who brings what, the oven times, and the shopping list.
Understand a Confusing Heating or Electric Bill with AI
See why your heating or electric bill went up.
Why you can trust these guides
Practice letters
Every guide has a made-up practice example, so you can try it with nothing at stake.
Answer keys
We show what a good AI answer should catch, so you know when it got something wrong.
Never asks for your details
No account needed, no trackers. We tell you what to cover up before you paste.
The printable starter card
The 5 rules every guide shares, on one page. Print it and keep it by your computer.
Common questions
- Do I need to pay for anything?
- No. The guides are free and work with the free versions of ChatGPT and Gemini.
- Is it safe to paste my letter?
- Cover or delete your Social Security, Medicare and account numbers, your name and address first. Never share a password or PIN.
- Can I trust what the AI says?
- Not on its own. Every guide ends with a check against the paper itself, and guide 8 shows how to catch mistakes.
- More questions?
- See Help and common questions.
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About us
Ask It, Check It is run by Dave Glaser. It is a small, independent site. We are not a government site, and we are not part of Medicare, OpenAI, Google or any company named in the guides.
Found a mistake? A way to tell us is coming soon.