Open Enrollment Money Checklist (Benefits for 2027)

By Cedar & Ledger

Late fall is when most people pick next year's health plan, either through work or the ACA Marketplace. The choice is easy to rush and then sits in every paycheck for twelve months. This checklist turns it into a money decision you can check with real numbers.

This is general information, not insurance, tax or financial advice. Every dollar figure is a made-up example. Dates and limits change: confirm them with your employer's benefits team or HealthCare.gov.

Quick checklist

• ☐ Find your deadline (employer window or Marketplace dates)
• ☐ Pull this year's actual medical, dental and vision costs
• ☐ Compare plans by total yearly cost, not just the premium
• ☐ Decide on an FSA or HSA amount, if offered
• ☐ Use up any 2026 FSA money you might lose
• ☐ Check life and disability coverage and beneficiaries
• ☐ Update your budget with the new paycheck deductions

Step 1: Find your deadline

Employer open enrollment windows are often only two or three weeks in November. For HealthCare.gov plans, recent years have run from November 1 to January 15, with a mid-December deadline for coverage starting January 1. Some states run their own marketplace with different dates. Put your date on the calendar today.

Step 2: Pull this year's real costs

Look at what you actually paid in 2026: copays, prescriptions, dental cleanings, glasses, any big visit. Your insurer's online claims history usually lists it. Add anything you already know is coming next year.

Step 3: Compare total yearly cost

The premium is only part of it. For each plan, estimate:

Yearly cost = premiums for 12 months + expected out-of-pocket costs (up to the plan's out-of-pocket maximum)

In this example, Plan B is cheaper in a normal year, but a bad year costs $1,920 more. If you pick a plan like B, keep enough savings to cover the gap. Always check that your doctors and prescriptions are covered before comparing prices.

Step 4: FSA or HSA amount

• FSA: set an amount close to costs you're fairly sure of. Unused money can be lost at year end unless your plan has a grace period or carryover. Ask which yours has.
• HSA: only available with an HSA-eligible high-deductible plan. The balance stays yours year to year. Check this year's IRS contribution limit and whether your employer adds money.

Step 5: Use 2026 FSA money you might lose

If you have an FSA balance, check the deadline and what counts as eligible: things like eye exams, glasses, contacts, prescriptions and some over-the-counter items. Keep the receipts.

Step 6: Life, disability and beneficiaries

While you're in the portal, check life and disability elections and make sure beneficiaries are current. It takes five minutes and is easy to forget for years.

Step 7: Update your budget

Your first January paycheck may be different. Put the new deductions into your budget, and plan a monthly set-aside for expected medical costs. Our medical and dental out-of-pocket budget guide walks through it.

Tools that help

The Medical Expense Tracker spreadsheet logs visits, bills, what insurance paid and what you owe, which makes next year's plan comparison quicker. The Paycheck Budget spreadsheet shows what each new paycheck has to cover.

Common questions

Is the cheapest premium the cheapest plan? Not always. Compare normal-year and bad-year totals, like the table above.

What if I miss open enrollment? You may have to wait until next year unless you have a qualifying life event, such as losing other coverage, moving, marriage or a new baby.

How much should I put in an FSA? Usually only what you're confident you'll spend, since some or all unused money can be lost.

Related template: the medical expense tracker template. Also see: Paycheck Budget Planner

See all Cedar & Ledger templates

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