Open Enrollment: How to Choose Benefits That Save You Money

1. Know Your Deadline and Your Year

   Employer open enrollment usually happens in the fall, and the dates are set by your employer — so look for the email or portal link now. The choices you make generally lock in for the whole next plan year unless you have a qualifying life event (like marriage, a birth, or losing other coverage). If you buy coverage on your own through the Marketplace, open enrollment for 2027 generally begins November 1 — check HealthCare.gov or your state exchange for the exact deadlines, which vary.

2. Compare Plans With Real Math

   Don't just compare monthly premiums. A plan's real cost is the premium you pay all year plus what you're likely to spend before it kicks in. Add up: yearly premiums, the deductible, copays and coinsurance for the care you expect, and the out-of-pocket maximum for the worst case. Then add any employer contribution to an HSA.

   A simple way to do it: estimate a low-use year (a few routine visits) and a high-use year (a surgery or a baby) for each plan, and compare the totals. The best plan is the one that works in both your likely year and your hard year. Check that your doctors and prescriptions are covered, too.

3. HDHP + HSA vs. PPO: Which Fits You?

   A high-deductible health plan (HDHP) usually has a lower premium and a higher deductible. Paired with a Health Savings Account (HSA), it can be a great deal: the money goes in tax-free, grows, and comes out tax-free for qualified medical costs. A PPO usually has a higher premium but lower upfront costs and more predictable copays.

   An HDHP tends to fit if you're healthy, you can cover the deductible from savings, and you'll use the HSA. A PPO tends to fit if you expect regular care, take costly prescriptions, or can't comfortably handle a large bill. If you'd put off care because of a high deductible, that's a sign to pick the more predictable plan. For 2027, the IRS says the HSA limit is $4,500 (self-only) or $9,000 (family), and a plan generally needs a deductible of at least $1,750 (self-only) or $3,500 (family) to qualify as an HDHP. Those are the IRS figures, not your plan's.

4. FSA vs. HSA: What's the Difference?

   • HSA: only with a qualifying HDHP; the money is yours, rolls over every year, and can go with you if you change jobs.
   • Health FSA: available with many plans; money is generally tied to your employer and may be lost if unspent (some plans allow a limited carryover). The 2026 limit is $3,400; check your plan's 2027 amount.

   Only put into an FSA what you're fairly sure you'll spend. For most people, the HSA is the more flexible account if they qualify. Generally, you can't contribute to both a general-purpose health FSA and an HSA in the same year, so ask HR which options you have.

5. Grab the 401(k) Match First

   If your employer matches contributions, that is part of your pay. Contribute at least enough to earn the full match — it's an immediate return you can't get elsewhere. Open enrollment is a good time to check your rate, your investments, and whether you're on track. The 2026 employee limit is $24,500, and you do not need to max it out. If you have high-interest debt, a balanced plan is fine: match first, then debt, then more savings.

6. Understand Life and Disability Basics

   Life insurance helps people who depend on your income. Employer-provided coverage is often a small multiple of your salary, which may or may not be enough — think through who depends on you, and what they would need. Disability insurance replaces part of your income if you can't work due to illness or injury; many people forget it, though a long illness is a bigger risk than many expect. Look at what your employer already provides, how much it pays, and how long it takes to start, then decide whether to add more. Check your beneficiaries while you're in there.

7. Look at Dependent Care and Other Perks

   If you pay for child care or care for a dependent adult so you can work, a Dependent Care FSA lets you pay with pre-tax dollars. The 2026 limit is $7,500 per household ($3,750 if married filing separately); confirm your plan's amount for the year you're enrolling in. Only enroll what you will actually spend. Also look for perks people skip: employee assistance programs, telehealth, legal plans, discounts, and student-loan help.

8. Confirm, Save, and Put It on the Calendar

   Before you submit, check the confirmation page and keep a copy. Put the deadline for any receipts or reimbursements on your calendar, and add the new payroll deductions to your budget so your take-home pay doesn't surprise you.

How FortuniFi Helps

New deductions change your take-home, so update your plan and see exactly how much you have for bills and debt each month. This Month shows what to pay first, your debt-free date shows the effect of a bigger 401(k) rate or a new premium, and Ask Fi can explain terms like “coinsurance” or “out-of-pocket maximum” in plain language.