Employer Open Enrollment Checklist 2026: Health Plan, FSA, HSA, 401(k)

The ten-step checklist

1. Compare total yearly cost, not only the premium. Add the premium for the year, the deductible and the out-of-pocket maximum for a realistic high-use scenario.
2. Check your doctors and prescriptions against each plan’s network and drug list.
3. Decide on a high-deductible plan with an HSA. The 2026 HDHP minimum deductible is $1,700 self-only and $3,400 family; the out-of-pocket maximum cannot exceed $8,500 / $17,000.
4. Fund the HSA. For 2026 the limit is $4,400 (self-only) or $8,750 (family), plus $1,000 at 55 and older. See the HSA guide.
5. Choose an FSA only if it fits. A health FSA ($3,400 in 2026) generally disqualifies an HSA; dental and vision limited-purpose FSAs do not. Compare FSA vs. HSA.
6. Use the dependent-care FSA if you pay for child or adult care: $7,500 per household in 2026.
7. Raise your 401(k) percentage. The limit is $24,500 (+$8,000 at 50+; $11,250 at 60–63). At minimum, contribute enough to get the full employer match. The retirement calculator shows the long-run effect.
8. Review life, disability and supplemental coverage. A life insurance number takes a few minutes with our life insurance calculator.
9. Update beneficiaries on retirement accounts, insurance and your HSA.
10. Save the confirmation and check that the first paycheck of the new year reflects your choices. Use the paycheck calculator to see what the deductions do to take-home pay.

Traps to avoid

• Picking a plan on premium alone. The cheapest premium often has the highest deductible.
• Forgetting that FSAs can forfeit unused money. Check whether your plan has a carryover (up to $680 in 2026) or a grace period.
• Having both a general-purpose FSA and an HSA. That makes HSA contributions ineligible.
• Joining Medicare while contributing to an HSA. HSA contributions must stop when Medicare coverage starts (details).
• Missing the window. Outside open enrollment you can usually only change benefits after a qualifying life event, such as marriage, birth or loss of coverage.

What changes for 2027

The IRS usually publishes next year’s limits for 401(k), IRA, HSA and FSA in the fall. Until then, 2026 numbers are the best guide. Once new numbers are official, the figures on this page update from one data file.

Estimates, not advice. CalcWyse figures use 2026 federal rules and the assumptions stated on this page (how we calculate). Your tax situation can differ. Confirm with a qualified tax professional or the IRS Tax Withholding Estimator before you act.