--- title: "Open Enrollment 2027: An AI Prompt to Compare Benefits | Candor" description: "Compare 2027 health plans and benefits with ChatGPT or Claude: what to give it, the questions it should ask, the key dates, and a worked example." url: "https://candor.money/explore/benefits-review" updated: "2026-10-18" --- # An open enrollment prompt to compare your 2027 benefits Give your AI the plan documents, not your memory of them: premiums, deductibles, out-of-pocket maximums, employer HSA contributions, and how your household uses care. Ask it to compare the total yearly cost of each plan in a light year and a bad year, and to list what to ask your benefits team before the deadline. [Get the prompt↓](#try-prompt) What your agent needs Current employer plan documents, enrollment dates, and household priorities. What you get back A side-by-side comparison, missing facts, and questions for your benefits team. When to use it A focused review when this question comes up. ## The prompt: Am I choosing the right benefits? Copy the prompt into the AI agent you use with Candor. It works from your Candor records and asks for anything it's missing. New to Candor? [Connect your agent first.](https://candor.money/connect) Your prompt Help me review my benefits choices in the context of my financial life in Candor. Ask for current plan documents, enrollment deadlines, household needs, and expected use. Compare verified premiums, coverage terms, employer contributions, and cash-flow implications. Identify relevant deadlines and questions for my benefits team. Do not infer insurance coverage or remaining deductibles from bank charges. Prepare a comparison for my review; do not enroll or change elections. Nothing runs until you send the prompt to your agent. ### New to Candor? Set up and start in one message Paste this into Claude, ChatGPT, or the agent you use. It sets up Candor and walks you through approving its access and connecting your accounts, then runs the prompt from your records. Set up Candor from https://candor.money/START.md and walk me through connecting it here. Help me review my benefits choices in the context of my financial life in Candor. Ask for current plan documents, enrollment deadlines, household needs, and expected use. Compare verified premiums, coverage terms, employer contributions, and cash-flow implications. Identify relevant deadlines and questions for my benefits team. Do not infer insurance coverage or remaining deductibles from bank charges. Prepare a comparison for my review; do not enroll or change elections. ## Not on Candor yet? Versions for ChatGPT and Claude. Both work from the documents you attach. With Candor, your agent also sees what your household paid for care this year and how much cash you keep, and it saves the choice and the reasons, so next year's enrollment starts from what you picked and why. ### For ChatGPT Help me compare my 2027 benefits before open enrollment closes on \[date\]. I've attached the plan summaries. For each health plan, pull out the premium per paycheck, deductible, out-of-pocket maximum, and any employer HSA contribution. Ask me how many doctor visits, prescriptions, and planned procedures we expect. Then compare the total yearly cost in a light year and a bad year. List anything the documents don't answer as a question for my benefits team. Don't guess coverage details. [Use ChatGPT with Candor](https://candor.money/connect/chatgpt) ### For Claude Attached are my employer's 2027 benefits documents. My household: \[who's covered, expected care, any planned surgery or baby\]. Build a side-by-side of the health plans with premiums, deductibles, out-of-pocket maximums, and employer contributions, then estimate each plan's yearly cost in a low-use and a high-use year. Note the enrollment deadline and anything else I need to elect, like an FSA or HSA amount. Mark which figures came from the documents and which are your estimates. [Use Claude with Candor](https://candor.money/connect/claude) ## What will the agent ask you? A good agent asks before it answers. Expect questions like these, and answer the ones that matter to you. * When does your employer's open enrollment close? * Who will be on the plan in 2027, and is anything big expected, like a surgery or a baby? * How many doctor visits and prescriptions did you have this year? * Are your doctors in each plan's network? * How much could you pay out of pocket in a bad year without going into debt? * Does your employer put money in an HSA, and how much? ## What does a good answer look like? A worked example on sample data: two adults choosing between a PPO and a high-deductible plan with an HSA, after a light year of care. The plan figures are illustrative, not from a real employer. You Which health plan should we pick for next year? Your agent Here's what the documents say. The PPO costs $260 a month in premiums, with a $1,000 deductible and a $5,000 out-of-pocket maximum. The high-deductible plan costs $120 a month, with a $3,600 deductible and an $8,000 maximum, and your employer puts $1,000 a year into the HSA. Your agent In a light year like this one, about $900 of care, the high-deductible plan comes out about $2,680 ahead: $1,440 in premiums plus $900 of care, less the $1,000 HSA deposit, is $1,340, against $4,020 for the PPO. Your agent In a bad year where you hit the maximum, it's $8,440 for the high-deductible plan and $8,120 for the PPO. So the question is whether you could cover $8,000 if you had to. Two things to ask HR before the deadline: whether your doctors are in network on both plans, and whether the HSA deposit arrives in January or per paycheck. Illustrative example with sample data, not a customer result. ## What does a weak answer look like? > A PPO is better if you see doctors often and want flexibility. A high-deductible plan is better if you're healthy and want lower premiums. Consider your needs and choose the plan that's right for you. * True of everyone, so it helps no one. It never used your plan's numbers. * It doesn't compare total yearly cost: premiums plus what you'd pay for care. * No deadline, no questions for HR, no check that your doctors are in network. ## Use current plan documents for the comparison Bank activity can show a payment but not the full terms of a benefit. Start with current employer documents, enrollment dates, and your household's expected use. Candor adds cash-flow context to the comparison; the documents establish premiums, coverage terms, and employer contributions. ### Check the answer * Confirm the plan year and enrollment deadline. Keep missing terms and questions for the benefits team visible beside each option. * Do not infer remaining deductibles, coverage, or eligibility from bank charges. Ask for the relevant source when those facts affect the comparison. ### Choose a next step Take the comparison and unresolved questions to your benefits team or relevant professional. The prompt prepares a decision; it does not enroll you or change an election. ## Where Candor fits Your agent works through the question with you, builds the plan, and keeps you on it. Candor gives it your real accounts, exact figures, and the goals, budget, notes, and decisions from earlier sessions, in whichever agent you use. Every week its review raises what's worth talking through and tells your agent why. Candor is not a licensed advisor and gives no advice; your agent does the advising, and the decisions are yours. * Read-only: Candor cannot move money. * Candor never sells your financial data or trains models on it, and you can export or delete it. * Every agent read and change is recorded with its reason. [Start free trial→](https://app.candor.money/signup)[Connect your agent](https://candor.money/connect) $0 today · card required · cancel anytime ## Common questions When is open enrollment for 2027 coverage? Employers set their own windows, so check your HR notice. On HealthCare.gov, enrollment for 2027 runs November 1, 2026 to January 15, 2027; enroll by December 15 for coverage that starts January 1\. State marketplaces can set different dates. What are the 2027 HSA contribution limits? $4,500 for self-only coverage and $9,000 for family coverage, per IRS Revenue Procedure 2026-24\. Employer contributions count toward the limit, and people 55 or older can add $1,000. Can ChatGPT or Claude choose my health plan? It can do the comparison: pull figures from the documents, total the yearly cost for different years, and list what to ask. Whether a bad year is affordable, and which doctors matter, is your call. It can't enroll you. What does Candor add at enrollment time? Your agent can see what you actually paid for care this year and how much cash you keep, and the decision and its reasons are saved for next year. Candor gives no advice; your agent does the comparing with you. ## Sources 1. [Dates and deadlines for 2027 health insurance](https://www.healthcare.gov/quick-guide/dates-and-deadlines/) HealthCare.gov 2. [Internal Revenue Bulletin 2026-25 (Rev. Proc. 2026-24)](https://www.irs.gov/irb/2026-25%5Firb) Internal Revenue Service, June 15, 2026 3. [Publication 969, Health Savings Accounts and Other Tax-Favored Health Plans](https://www.irs.gov/publications/p969) Internal Revenue Service ## Keep exploring. [HouseholdAm I paying the right amount for insurance?Review costs and coverage alongside what has changed in your life.One-time review](https://candor.money/explore/insurance-review)[Big decisionsCan I afford to work less or take time off?Explore how a break or income change would affect your runway.One-time review](https://candor.money/explore/time-off)[Where I standHow did this year go, and what's next?Bring your money, life changes, and open questions together.One-time reviewFull guide](https://candor.money/explore/annual-review) ## Ask it with your own numbers. Connect your accounts to Candor, then send this to the agent you already use. It answers from your real records and keeps the plan for next time. [Start free trial→](https://app.candor.money/signup)[Connect your agent](https://candor.money/connect) $0 today · card required · cancel anytime