Practical AI: Use a free AI assistant to compare 2027 health plans on Oregon's new Explore Health (Nov. 2)

A free AI chat assistant can help you line up health plan costs side by side, but the numbers should come from the plans themselves. Photo: Daniel Sone, National Cancer Institute / Wikimedia Commons, public domain

Quick Read

• Open enrollment for 2027 health coverage on Explore Health, Oregon's new state-run marketplace, began Nov. 1 and runs through Jan. 15, 2027; sign up by Dec. 31 for coverage that starts Jan. 1.

• Providence and PacificSource will not sell individual plans in Oregon in 2027, and Moda will not be offered in eight counties, including Marion and Polk.

• A free AI chat assistant can turn the costs from a few plans into a side-by-side table and estimate what each would cost you in a light year and a heavy year.

• Keep your Social Security number, income records and member ID numbers out of the chat, check every figure against the plan's own documents, and do the actual enrollment yourself or with free local help.

This is Practical AI, the weekly Willamette News column on everyday ways to put AI tools to work. This week's task has a deadline attached: picking a 2027 health plan.

If you buy your own health insurance in Oregon, the shopping looks different this fall. Oregon has moved from the federal HealthCare.gov platform to its own marketplace, Explore Health, which opened for 2027 sign-ups on Nov. 1, the Oregon Health Authority said. Open enrollment runs through Jan. 15, 2027, and you need to enroll by Dec. 31 for coverage that starts Jan. 1, according to Explore Health.

The plan lineup changed, too. Providence and PacificSource will not offer individual health insurance in 2027, and Moda will not be available in Crook, Deschutes, Klamath, Lake, Marion, Polk, Umatilla or Union counties, Explore Health says. The state's final 2027 rate sheet from the Oregon Division of Financial Regulation lists four insurers in the individual market, BridgeSpan, Kaiser, Moda and Regence, with an average rate increase of 21.6%. People whose insurer is leaving have been matched with a plan from another company that may be used for automatic re-enrollment, but the state encourages everyone to shop and compare.

Comparing plans means juggling premiums, deductibles, out-of-pocket maximums and copays at the same time. That is a good job for an AI assistant: it can organize numbers you give it and run the what-if math while you make the decisions.

Try it: a 20-minute plan comparison

1. Go to ExploreHealthOR.gov and open the Plan Guide. It lets you compare plans in your area without creating an account, and you can enter your doctors and prescriptions there to see which plans fit. Do that part on the official site, not in an AI chat.

2. Pick two to four plans. For each one, write down the plan name, metal tier, estimated monthly premium after any financial help the Plan Guide shows, deductible, out-of-pocket maximum, and the copays you care about, such as primary care, specialist visits and generic drugs.

3. If a number is unclear, open the plan's Summary of Benefits and Coverage, a short, plain-language form every plan must provide so shoppers can make apples-to-apples comparisons.

4. Open a free AI chat assistant, such as ChatGPT, Google Gemini, Microsoft Copilot or Claude. Paste in only the plan numbers. Leave out your name, address, birth date and any ID numbers.

5. Add this prompt: "Here are the 2027 costs for [number] health plans I'm considering. Build a table comparing the monthly premium, deductible, out-of-pocket maximum and the copays I listed. Then estimate my total cost for a full year on each plan in two cases: a light year with three primary care visits and one generic prescription filled every month, and a heavy year where I reach the out-of-pocket maximum. Show your math, list every assumption you made, and tell me what information is missing. Note: these are Oregon plans, and Oregon Standard plans cover some office visits with a copay before the deductible."

6. Ask follow-up questions in plain language, such as "Which plan comes out ahead if I see a specialist six times?" or "Explain the difference between a deductible and an out-of-pocket maximum."

7. Check the AI's figures against the Plan Guide or each plan's summary. Then enroll on Explore Health yourself.

Oregon details to tell your AI

AI tools are trained on older information and may not know how Oregon's 2027 market works. They may even point you to HealthCare.gov. Paste in the facts that matter, from Explore Health's plan pages:

• Oregon Standard plans cover office visits before the deductible with a copay, and every Standard plan includes three office visits at $5 each before you reach your deductible.

• Cost-sharing reductions, which lower deductibles and copays, are available only on eligible Silver plans.

• Oregon insurers are not offering Catastrophic plans for 2027.

• For 2027, job-based coverage is generally considered affordable if employee-only coverage costs less than 10.22% of household income, Explore Health says. If your job's plan costs more than that, you may still qualify for financial help.

Going one step further: let an agent gather the plans

Some AI tools can now browse websites and click through pages for you. That is the agentic side of AI. OpenAI says cloud browser in ChatGPT Work can read web pages, click buttons and fill in forms on its own browser in the cloud, on paid plans other than Free and Go. Google's auto browse in Gemini in Chrome can complete multi-step web tasks for Google AI Pro and Ultra subscribers in the U.S. who are 18 or older.

You could ask one of these agents to open the Plan Guide and gather the Silver plans for your county into a table. If you try it, tell it in plain words not to create an account, sign in or submit anything. Watch what it types into each form, and approve each new website yourself. Google says Gemini may share your personal info with the sites it uses, and OpenAI says to check the result and its sources before relying on it. Some websites also block automated browsers.

Keep the final steps for yourself: signing in to Explore Health, entering income and household details, choosing a plan and paying. No AI tool should apply for coverage on your behalf.

What to watch out for

• Privacy: anything you paste may be stored by the AI company. Never paste your Social Security number, tax returns, pay stubs, member or account numbers, or passwords. You do not need them to compare plan costs.

• Accuracy: AI can get math wrong or invent plan details and sound sure of itself. Treat its table as a draft and check each number against the plan's own documents.

• Doctors and drugs: whether your doctor is in network or your medication is covered is a yes-or-no fact. Get it from the Plan Guide or the insurer, not from an AI guess.

• Advice: Explore Health notes that only licensed insurance agents can recommend which plan is best for you. AI can help you understand the options, not make the choice.

• Free help: Explore Health's Enrollment Partners, licensed agents and trained assisters, help at no cost. You can also call Explore Health at 855-268-3767, Monday to Friday, 8 a.m. to 6 p.m.

Sources

Oregon Health Authority: Oregon to Launch Explore Health this November (Aug. 21, 2026)

Oregon Health News Blog, Oregon Health Authority: Explore Health launches tool to help people navigate health coverage options for 2027 (Oct. 15, 2026)

Explore Health: Enrollment Dates (accessed Nov. 2, 2026)

Explore Health: Automatic Re-enrollment, Changes to Oregon Individual Health and Dental Plans in 2027 (accessed Nov. 2, 2026)

Explore Health: Health Plans (accessed Nov. 2, 2026)

Explore Health: Financial Help (accessed Nov. 2, 2026)

Explore Health: Get Help (accessed Nov. 2, 2026)

Oregon Division of Financial Regulation: ACA-Compliant Plans 2027 Health Insurance Rate Requests and Final 2027 Individual Plan Coverage by County (October 2026)

HealthCare.gov: Summary of Benefits and Coverage (accessed Nov. 2, 2026)

OpenAI Help Center: Using cloud browser in ChatGPT (accessed Nov. 2, 2026)

Google Chrome Help: Ask Gemini in Chrome to complete tasks for you with auto browse (accessed Nov. 2, 2026)

Cover photo: Stethoscope and Laptop Computer, by Daniel Sone, National Cancer Institute, via Wikimedia Commons, public domain

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Practical AI runs weekly. Willamette News is not affiliated with any AI company or insurer named in this story and received nothing for mentioning them. This column is general information, not insurance advice.