Open Enrollment 2027: Your Step-by-Step Checklist

1. Step 1 Find your deadline and what's changing

   Open your employer's enrollment guide and note the deadline (add it to your calendar above). Look for premium changes and plans that are new or going away. If you do nothing, many employers roll your health plan over, but flexible spending accounts usually have to be chosen again every year.

2. Step 2 Check who you're covering

   A marriage, a baby, a divorce, a child turning 26 or a spouse with new coverage at work all change the best choice. Outside open enrollment you can change plans only after a qualifying life event, and you usually have just 30 days to ask (Department of Labor).

3. Step 3 Compare health plans on total yearly cost, not the premium

   Add a year of premiums to the bills you're likely to pay before the plan pays (deductible and coinsurance), then subtract any employer HSA money and the tax you save. A cheaper premium can cost more in a year with a hospital stay.

   Compare HDHP vs PPO costs

4. Step 4 Check doctors, hospitals and prescriptions

   Look up your doctors and nearest hospital in each plan's network, and your prescriptions in each plan's drug list (and which tier they're on). Network changes are the most common January surprise.

5. Step 5 Choosing a high-deductible plan? Set your HSA amount

   For 2027 you can put in up to $4,500 with self-only coverage or $9,000 with family coverage, counting your employer's money, plus $1,000 at 55 or older (IRS). Through payroll it also skips Social Security and Medicare tax, the money never expires, and you can change the amount going forward, usually at least monthly. Married couples share one family limit.

   See your HSA tax savings

6. Step 6 Elect a health FSA only for costs you're sure of

   The 2027 health FSA limit is $3,500 (projected). Count only predictable costs: glasses, dental work, prescriptions, regular copays. Unused money is lost unless your plan offers a carryover (up to $700 (projected)) or a grace period of up to 2½ months; a plan can offer one or neither (IRS Publication 969). With an HSA, a regular health FSA (yours or your spouse's) makes you ineligible; only a limited-purpose (dental and vision) or post-deductible FSA is allowed.

   Check how much FSA money is at risk

7. Step 7 Paying for child care? Decide on a dependent care FSA

   Since 2026 a household can set aside up to $7,500 ($3,750 if married filing separately) for care of children under 13 (or a spouse or adult dependent who can't care for themselves) (26 U.S.C. § 129). Depending on income, the child and dependent care credit can be worth more, so compare before you elect.

   Compare the FSA with the credit

8. Step 8 Review life and disability insurance

   Employer-paid group life cover above $50,000 adds taxable "imputed income" to your pay (IRS Publication 15-B). If you can pay disability premiums with after-tax money, benefits you'd receive are generally tax-free. Update beneficiaries while you're there.

9. Step 9 Set your 2027 401(k) contribution

   At the very least, contribute enough to get the full employer match. The 2027 limit is $25,500 (projected), plus catch-ups from age 50 (larger at 60–63). If your prior-year Social Security wages topped $150,000, catch-ups must go in as Roth. Many plans let you change the rate here or any time.

   See what a contribution costs per paycheck

10. Step 10 Pick up the smaller pre-tax perks

    Commuter benefits let you pay for transit and work parking before tax: up to $350 (projected) a month each in 2027. Check for others your employer offers, such as an employer HSA deposit for completing a wellness step.

11. Step 11 See your January paycheck with every election

    Premiums, HSA or FSA, 401(k) and commuter money all change your take-home pay, and each is taxed differently. Check the total before you submit.

    Check your take-home after open enrollment

12. Step 12 Submit, save the confirmation, check your first 2027 pay stub

    Keep the confirmation page or email. In January, compare the deductions on your first pay stub with what you chose; payroll errors are easiest to fix early.

    Check your 2027 paycheck

All done. Nice work: check your first 2027 pay stub or plan statement in January.

1. Step 1 Know the three dates

   Open enrollment for 2027 coverage runs November 1, 2026 to January 15, 2027 on HealthCare.gov. Pick a plan by December 15 for coverage from January 1; plans picked later start February 1 (HealthCare.gov). A court threw out a rule that would have ended the window on December 15, but the government has appealed, so don't count on the January window: check HealthCare.gov. State marketplaces can set their own dates.

2. Step 2 Update your application and your 2027 income estimate

   Your premium tax credit depends on the household income you expect for 2027. The extra credits of 2021–2025 expired, so households above 400% of the poverty level generally get no credit again, and many others get less (IRS; KFF). Estimate honestly: from 2026 there's no cap on paying back credits that turn out too high, so the full excess comes off your refund or adds to your tax bill.

3. Step 3 Don't let your plan renew without looking

   Insurers proposed a median 15% premium increase for 2027 (Peterson-KFF), and the credit that offsets it may have changed too. If you do nothing you may be renewed into the same or a similar plan at the new price, so compare first.

4. Step 4 Compare metal levels on total cost

   Bronze plans have the lowest premiums and the highest deductibles; gold the reverse. If your income is up to 250% of the poverty level, a silver plan comes with cost-sharing reductions that lower your deductible and copays, and only silver plans get them (HealthCare.gov).

   Compare two plans' yearly cost

5. Step 5 Check doctors, hospitals and prescriptions

   Marketplace plans often have narrow networks. Search each plan's directory and drug list before you choose, not after.

6. Step 6 Picking bronze or catastrophic? You can open an HSA

   Since 2026, bronze and catastrophic plans count as HSA-compatible (IRS). For 2027 you can contribute up to $4,500 (self-only) or $9,000 (family) and deduct it, even without itemizing. You can't have other non-HSA health coverage at the same time.

   Estimate your HSA tax savings

7. Step 7 Self-employed? Plan the health insurance deduction

   Premiums for you and your family are usually deductible as self-employed health insurance, unless you were eligible for a subsidized employer plan (yours or a spouse's) for that month, and only up to your business profit. Build it into your estimated tax payments.

   Estimate your self-employment tax

8. Step 8 Pay the first premium on time

   Coverage doesn't start until the insurer receives your first payment. Then set up automatic payments so a missed bill can't end your coverage.

All done. Nice work: check your first 2027 pay stub or plan statement in January.

1. Step 1 Know the windows

   Medicare open enrollment runs October 15 to December 7, 2026, for changes from January 1, 2027. If you're in a Medicare Advantage plan, you get one more switch between January 1 and March 31, 2027 (to another Advantage plan or to Original Medicare) (Medicare.gov).

2. Step 2 Read your plan's Annual Notice of Change

   Plans send it by September 30. Look for changes to the premium, deductible, drug list, pharmacies and doctors. Even a plan you liked can change a lot in a year.

3. Step 3 Re-check your drugs in Medicare's Plan Finder

   Enter your prescriptions and pharmacy on Medicare.gov's Plan Finder to compare total yearly drug costs. Part D out-of-pocket drug costs are capped at $2,400 in 2027 (up from $2,100), and no plan's deductible can exceed $700 (Medicare.gov), so the premium and the drug list matter more than ever.

4. Step 4 Compare Original Medicare + Medigap with Medicare Advantage

   Advantage plans often have low premiums but networks and a yearly out-of-pocket maximum; Medigap costs more each month but makes bills predictable. Compare them in a typical year and a bad one.

   Compare Medicare costs

5. Step 5 Leaving Advantage? Check Medigap first

   Outside your Medigap open enrollment period (the six months starting when you're 65 and on Part B), insurers in most states can turn you down or charge more because of your health. Exceptions: within 12 months of trying Medicare Advantage for the first time you may have "trial rights" to a policy, and some states (such as New York and Connecticut) guarantee access. Line up a Medigap policy before you drop an Advantage plan.

6. Step 6 Check the income surcharge (IRMAA)

   2027 Part B and Part D premiums use your 2025 tax return. If your income has since dropped because of retirement or another life-changing event, you can ask Social Security to use a newer year (Form SSA-44).

   Check your IRMAA tier

7. Step 7 Get free, unbiased help

   Your State Health Insurance Assistance Program (SHIP) gives free one-to-one Medicare counseling, and 1-800-MEDICARE can enroll you by phone. Low income? Ask about Extra Help with drug costs.

All done. Nice work: check your first 2027 pay stub or plan statement in January.