โOpen enrollment is here and I'm staring at plan names, premiums, deductibles and networks I can't line up side by side.โ
A chat assistant can turn the plan summaries you already have into one side-by-side table and show what each plan would cost you in a quiet year and in a busy year, using only the numbers you paste in. You still choose the plan; the AI just does the lining up and the math so you can see the trade-offs and know what to ask.
Fix it yourself in 3 steps
Download the Summary of Benefits and Coverage (SBC) for each plan you're considering, from your employer's benefits site or your state or federal Marketplace. Write down roughly how you used care last year (doctor visits, prescriptions by name only, any planned procedure) without diagnoses, member IDs or account numbers.
Paste the prompt below with the plan numbers and your usage notes. Check every figure in the table against the SBC; if anything doesn't match, correct it and ask for the table again.
Take the questions it lists to HR, the Marketplace help line or the insurer (for example, whether your doctors and medicines are covered), then pick and enroll yourself on the official site before your deadline, and put the deadline on your calendar.
Copy this prompt
Help me compare health plans for open enrollment. Plans (from each plan's Summary of Benefits and Coverage): [for each plan: name, monthly premium, deductible, out-of-pocket maximum, copays/coinsurance for doctor, specialist, urgent care, ER and generic/brand drugs, HSA-eligible yes/no, network type]. Who's covered: [me / me + spouse / family]. Rough use last year: [e.g. 4 doctor visits, 1 specialist, 2 regular prescriptions, any planned procedure], no diagnoses. Rules: 1) Use only the numbers I give you; if a number is missing, write 'not given' and don't guess. 2) Make a side-by-side table of the plan numbers. 3) Estimate yearly cost for each plan (premiums plus what I'd pay for care) in three cases: a quiet year, a year like last year, and a worst case where I hit the out-of-pocket maximum. Show the math. 4) List 5 questions to ask before choosing, such as whether my doctors and medicines are in network. 5) Don't recommend a plan and don't give medical, tax or financial advice; point out trade-offs only. Stop after the table, the estimates and the questions, and wait for my corrections.
Type your details in the boxes above the message, then tap Copy & open. Leave a box empty if you're not sure.
Tips from people who've done it
Use the official Summary of Benefits and Coverage for each plan; marketing pages often leave out the out-of-pocket maximum and drug tiers.
Check the provider directory and drug list (formulary) yourself for the doctors and medicines you rely on; a cheaper plan that drops them can cost more.
Skip diagnoses, member IDs and Social Security numbers. 'Two regular prescriptions and a specialist every quarter' is enough for the math.
Dates differ by plan: HealthCare.gov's 2027 open enrollment runs Nov 1, 2026 to Jan 15, 2027 (enroll by Dec 15 for Jan 1 coverage); state Marketplaces and employer plans set their own deadlines.
HR or benefits teams handling employees' health details should use a business plan of their AI tool with a signed BAA, or keep personal details out of the chat.
Agents people used for this: Grok Bot, ChatGPT, Gemini, Claude.
Quick answers
Can AI tell me which health plan to pick?
No. It can line up the numbers from each plan's Summary of Benefits and Coverage and estimate what you'd pay in a quiet, normal and worst-case year, but the choice is yours. Check doctors and medicines with the plan, and ask HR, the Marketplace or a licensed agent if you need help deciding.
What should I paste in to compare plans?
Premiums, deductibles, out-of-pocket maximums, copays or coinsurance and drug tiers from each plan's Summary of Benefits and Coverage, plus a rough count of last year's visits and prescriptions. Leave out diagnoses, member IDs and Social Security numbers.
When is open enrollment?
On HealthCare.gov, open enrollment for 2027 plans runs November 1, 2026 to January 15, 2027; enroll by December 15 for coverage starting January 1. State Marketplaces and employer plans can have different deadlines, so check yours.
Black out account and card numbers before sharing anything. Never give an AI your bank password โ export statements instead. AI drafts; you approve and send. Not financial, legal or tax advice.
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