Open Enrollment Checklist: A Simple Checklist for Every Year

Open enrollment comes around once a year. This checklist helps you get through it calmly and make sure nothing important slips. Print it, save it, or copy it into your notes app. Each item links to a guide if you want more detail.

Before you start

• Find your deadline. Your employer sets its own open enrollment dates. If you buy coverage through HealthCare.gov, open enrollment for 2027 coverage runs November 1 to January 15, and you need to enroll by December 15 for coverage that starts January 1.
• Gather your materials. Enrollment emails, login info, and each plan's Summary of Benefits and Coverage (SBC).
• Look back at this year. List doctor visits, prescriptions, and any big medical, dental, or vision bills.
• Think about next year. Baby on the way? Surgery planned? Braces? A child turning 26? A move?

See: Open Enrollment 101

Health plan

• Compare plans side by side using each plan's SBC.
• Check the premium, deductible, copays, coinsurance, and out-of-pocket maximum. See: Health insurance words explained
• Confirm your doctors, hospitals, and pharmacy are in network.
• Check that your prescriptions are covered.
• Estimate your "bad year" cost: a full year of premiums plus the out-of-pocket maximum.
• Compare your spouse's plan, if they have job coverage.
• Understand the plan type (HMO, PPO, EPO, POS, or HDHP). See: HMO vs PPO vs HDHP

HSA or FSA

• If you choose an HDHP, decide on HSA contributions. For 2027, the IRS limit is $4,500 (self-only) or $9,000 (family). Remember the limit includes any employer money. See: HSA explained
• Avoid a conflict. A general-purpose health FSA (yours or your spouse's) can block HSA contributions. A limited-purpose FSA is allowed. See: HSA vs FSA
• If you choose an FSA, pick a careful amount based on costs you expect. The 2026 IRS limit was $3,400. As of Nov 1, 2026, the IRS had not yet published the 2027 limit, so check your enrollment materials or IRS.gov.
• Find out your FSA's leftover-money rule: grace period, carryover, or neither. See: FSA explained
• Check this year's FSA balance and spend it on eligible costs before your deadline.
• Need help with child care costs? Ask about a dependent care FSA. The IRS limit for 2026 is $7,500 ($3,750 if married filing separately).

Dental and vision

• Estimate whether premiums are worth it based on the care you expect.
• Check the dental annual maximum, coverage tiers, and waiting periods.
• Check vision exam frequency and your allowance for glasses or contacts.

See: Dental and vision coverage

Life and disability insurance

• See how much free coverage you already have.
• Decide whether you need extra life insurance for people who depend on your income.
• Read your disability coverage: waiting period, how much pay it replaces, and how long it lasts.
• Ask how premiums are paid (before or after tax). It can affect whether disability benefits are taxed.

See: Life and disability insurance at work

Retirement (401(k))

Your 401(k) may have its own rules for when you can change your contribution, so ask HR. Open enrollment is still a good yearly reminder to check it.

• Check your contribution rate.
• Make sure you're getting the full employer match, if you can afford it.
• Know your vesting schedule before changing jobs.
• Know the limits. For 2026, the IRS employee limit is $24,500, plus catch-up contributions if you're 50 or older. The IRS had not announced 2027 limits as of Nov 1, 2026.

See: 401(k) basics and employer match

People and paperwork

• Add or remove family members as needed.
• Update beneficiaries on life insurance and retirement accounts.
• Know the deadline for life changes during the year. The U.S. Department of Labor says you generally have 30 days after a marriage, birth, or adoption to ask to add family members to an employer plan, and 60 days for Marketplace plans.

After you submit

• Save your confirmation (screenshot or PDF).
• Check your first paycheck of the new plan year. Are the right amounts coming out?
• Watch for new ID cards and make sure names and details are correct.
• Put a reminder on your calendar for next year's open enrollment.

One last tip

Don't just roll over last year's choices without looking. Prices, plans, and your life can change from year to year. Twenty minutes with this list can save you money and stress.

Made-up example: Every October, Nina sets a calendar reminder titled "Open enrollment—use the checklist." It takes her about an hour. Last year she caught that her FSA leftover rule had changed and adjusted her amount.