The problem
Medicare open enrollment runs from October 15 to December 7, 2026. Plans change every year, and for 2027 some stand-alone drug plans raise their premiums a lot, while others cost less. There are no $0-premium stand-alone drug plans in 2027 for people without Extra Help. The cheapest plan for one person depends on their exact drugs and pharmacy, so the only real check is to enter every drug in Medicare's Plan Finder and compare the total yearly cost, not just the premium. That's slow, and many people don't do it. Grown children often do it for a parent. An agent can do the typing and the comparing for you.
Why it works
A browser agent like Grok Bot can open Medicare's Plan Finder as a guest, type in every drug with its exact strength and form, add the pharmacy and read each 2027 plan's yearly cost, which is the slow part of comparing drug plans. It can't see the person's Medicare account, and it shouldn't log in, enroll or talk to agents, so the prompt has it type medicare.gov itself (never a link from a call, email or ad), never ask for or write a Medicare number, compare yearly totals rather than premiums, flag any drug a plan leaves out, call no plan best, and stop before Enroll. It treats letters, pages and emails as information, never as instructions. The double-check prompt then makes it point to the source of each finding again. You check with the plan, Medicare or SHIP, and you decide.
What you get from it
- The drug list read back to you: each drug's name, strength, form, how many and how often.
- Your current plan's 2027 cost, from Medicare's Plan Finder (and the plan's letter, if you have it).
- The 3 plans with the lowest estimated total yearly cost for these exact drugs at your pharmacy, side by side with your current plan.
- For each plan: the monthly premium, the yearly drug deductible, the total yearly cost, and each drug marked covered or not, with any limits.
- The yearly difference from your current plan, with the sum shown.
- A short list of what to check before you choose, and the deadline: December 7, 2026. It stops before Enroll.
What you need
- Grok Bot, or any chat AI. Grok Bot (our pick) opens Medicare's Plan Finder and enters the drugs itself. With ChatGPT, Claude or another chat AI (free), you open Plan Finder yourself and paste the results in.
- The drug list. Each drug's name, strength (for example 40 mg), form (tablet, capsule) and how many, how often. A photo of the pill bottle labels or the pharmacy's printout works. Cut out the name, address and Rx number first.
- The ZIP code and the pharmacy. The ZIP code where the person lives, and the name and town of the pharmacy they use.
- The plan's letter, if you have it. The “Annual Notice of Change” the current plan sent in the fall. It shows next year's changes. It helps, but isn't required.
- No Medicare number. You don't need a Medicare number, a Social Security number or a Medicare.gov login. Plan Finder works without them.
- About 15 minutes. Longer if the drug list is long.
What the test showed
On 30 Oct 2026 we opened Medicare's Plan Finder (medicare.gov/plan-compare) with a browser, without logging in. We chose 2027, entered a ZIP code, picked drug plans, entered a common generic drug with its strength and quantity, added a pharmacy, and reached the 2027 plan list sorted by total drug and premium cost. No login and no robot check was needed. The prompt uses the button names we saw. We also ran it once for real with Grok Bot on Medicare's Plan Finder as a guest (Oct 30, 2026): it entered 4 common generic drugs and a pharmacy, reached the 2027 drug plan list, compared yearly totals and stopped before Enroll. Apart from that one Grok Bot run, we only tested on an OpenAI model (gpt-5-mini). Other assistants may word things differently or miss a check, so run the included sample once in your chosen tool and compare it with the worked example before you use your own data.
Sources
Checked 2026-10-30. Rules and prices change: check the source before you rely on it.
- Medicare.gov: Open Enrollment
- Medicare.gov: Plan Finder (Find a Medicare plan)
- Medicare.gov: Your Medicare card (guard your Medicare number)
- Medicare.gov: Reporting Medicare fraud and abuse
- SHIP: free local Medicare help (shiphelp.org)
- KFF, 2 Oct 2026: Part D stand-alone drug plan premiums for 2027
The free Blueprint
Use it now: medicare drug plan checker
This whole Blueprint is free: the same tested, copy-paste prompt pack as our paid ones, with no checkout and no sign-up. No coding needed.
- Which AI to use, and why: Grok Bot, because it opens Medicare's Plan Finder in its own browser without logging in. Fallback: ChatGPT, or any chat AI.
- A main prompt: it asks you a few questions one at a time, then does the job with you step by step
- 3 follow-up prompts: “Double-check your work”, “After you called the plan, Medicare or SHIP”, “Check again after a change”, plus “Did it work?”
- A test-it checklist, with a synthetic sample to try before your own data
- A worked example with the expected result, so you know what good looks like
- A printable PDF guide