Insurance

Open Enrollment Checklist: How to Pick Benefits Without Leaving Money on the Table

Open enrollment is your once-a-year chance to change health plans and other benefits. This checklist walks through what to compare, from deductibles to HSAs and disability coverage.

Table of contents

Every fall, millions of people click “keep my current elections” without a second look. Benefits change every year — premiums, deductibles, provider networks, prescription coverage — and so does your life. Spending an hour on open enrollment can save hundreds or even thousands of dollars.

Know your deadline

  • Employer plans: usually a few weeks in the fall. Check your HR portal.
  • ACA marketplace: in most states, open enrollment on HealthCare.gov runs from November 1 to January 15, with a mid-December deadline for coverage starting January 1. Some states that run their own exchanges have different dates.
  • Medicare: the annual enrollment period runs October 15 to December 7.

Outside these windows, you generally can only change plans after a qualifying life event like marriage, a birth, or losing other coverage.

Step 1: Review last year

  • How much did you spend on premiums and out-of-pocket care?
  • Did you hit your deductible or out-of-pocket max?
  • Any big changes coming — a baby, surgery, new prescriptions, a move?

Step 2: Compare total cost, not just premiums

For each plan, estimate:

  • Annual premiums
  • Expected out-of-pocket costs in a typical year
  • Worst case: premiums plus out-of-pocket max

The cheapest premium isn’t always the cheapest plan. If any terms are fuzzy, read health insurance terms explained.

Step 3: Check networks and drugs

  • Are your doctors, hospitals, and specialists in-network?
  • Are your prescriptions on the formulary, and at what tier?
  • Do you need referrals?

Step 4: Consider an HDHP with an HSA

If you’re generally healthy, a high-deductible plan with a health savings account can make sense, especially if your employer contributes to the HSA. The tax benefits are significant — see the HSA triple tax advantage. Just make sure your emergency fund could cover the deductible.

Step 5: Decide on FSAs

  • Health care FSA: pre-tax money for medical costs. Be conservative — unused funds may be forfeited beyond limited carryover.
  • Dependent care FSA: pre-tax money for childcare or eldercare. The annual limit was increased under recent federal law; check your plan.

Step 6: Don’t skip the “boring” benefits

  • Disability insurance: often cheap through work and important. See disability insurance explained.
  • Life insurance: group coverage is a good base, but may not be enough. See how much term life you need.
  • Dental and vision: compare premiums with what you’d actually use.
  • Legal plans, pet insurance, identity protection: only if the value is clear.

Step 7: Revisit retirement contributions

Open enrollment is a natural time to bump your 401(k) contribution, especially for next year’s new limits. Make sure you’re getting the full employer match.

Step 8: Update beneficiaries and dependents

Add new family members, remove ones who no longer qualify, and double-check beneficiaries on life insurance and retirement accounts.

Marketplace shoppers: check your subsidy

Premium tax credits on the ACA marketplace depend on your expected income and household size, and the rules for how much help is available have changed in recent years. Update your income estimate carefully when you apply, and report changes during the year to avoid owing money at tax time.

Bottom line

Don’t auto-renew without looking. Compare total costs, check networks and prescriptions, consider an HSA, and review disability, life, and retirement benefits. Save a screenshot of your confirmed elections. One focused hour now can make your whole next year cheaper and safer.

About Ethan Wilson

Writes plain-English money guides for Financial Achieve.

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