Open Enrollment 2027: 9 Health Insurance Checks Before You Choose

Choosing health insurance for 2027 starts with two questions: Which enrollment rules apply to you, and what will the coverage actually cost when you need care? A familiar plan name or a low monthly premium cannot answer either question.

Medicare’s annual plan-change window runs October 15–December 7, 2026. HealthCare.gov enrollment begins November 1. Medicaid and CHIP accept applications year-round, while employers set their own annual enrollment schedules. Use the nine checks below to compare the options available to you—and make a choice that fits your care needs and budget.

Sources: Medicare: annual open enrollment; HealthCare.gov: enrollment dates and coverage start dates; HealthCare.gov: Medicaid and CHIP applications.

Start with your situation: Medicare · Medicaid or CHIP · Coverage through work · Marketplace and tax considerations · Comparison worksheet

Medicare and Medicaid have different eligibility rules; some people qualify for both. The choices below are not a menu of programs everyone can freely enter. This guide provides general U.S. information for 2027 coverage. Your eligibility, state rules, and plan documents determine your options.

Gather these before you compare

• Your enrollment notice and the exact 2027 plan names or IDs.
• The Summary of Benefits and Coverage for work or Marketplace plans; Medicare plan documents and the Annual Notice of Change where applicable.
• A list of providers, ongoing services, prescriptions, dosages, and pharmacies to check privately against the plans.
• Household premium quotes, employer contributions, and a realistic estimate of next year’s care and household income.

Keep account numbers, Social Security numbers, Medicare numbers, and personal medical details out of the worksheet. You need comparison notes, not a second medical record.

A Summary of Benefits and Coverage provides a common starting point for comparing individual and job-based plans. Read the full plan terms when a limitation could change your choice.

1. Match your deadline to your coverage

Which path should you compare?

Start with eligibility, then compare the plans within reach. Medicare primarily serves older adults and certain people with disabilities or qualifying conditions. Medicaid and CHIP use program and state eligibility rules. Employer coverage depends on the job’s benefits rules; Marketplace assistance depends on household circumstances. Some people have more than one source of coverage and need coordination advice.

When you contact a program or benefits administrator, ask three questions: Am I eligible? When can I enroll or change? When does coverage actually start? A plan-choice deadline is not necessarily an application, renewal, or premium-payment deadline.

Put your own deadline on the calendar before you start shopping. A spouse, parent, or adult child may have a different deadline and may need a different coverage path.

Coverage	When to act
Medicare annual plan changes	October 15–December 7, 2026. Eligible changes generally take effect January 1, 2027.
HealthCare.gov Marketplace	November 1, 2026–January 15, 2027. Select by December 15 for January 1 coverage; later selections generally start February 1. Pay the first premium on time. State-run exchange schedules may differ.
Medicaid / CHIP	Apply throughout the year. Follow your state’s renewal notice and any separate managed-care plan-choice deadline.
Employer coverage	Use the employer’s enrollment dates, plan year, and election instructions. There is no single national annual window.
Medicare Advantage open enrollment	January 1–March 31, 2027, for current Medicare Advantage enrollees. This permits certain changes; it is not an unrestricted second enrollment window for everyone.

New to Medicare? Initial Part A and Part B enrollment follows separate rules. Losing a job, moving, or losing other coverage may also create a special enrollment opportunity. Ask promptly: different programs use different deadlines, and waiting for fall may leave a gap.

Sources: Medicare: when you can join or change plans; HealthCare.gov: enrollment dates and coverage start dates; Medicaid.gov: find your state agency; Department of Labor: making your health benefits work.

2. Compare annual costs—and a difficult year

A premium is the recurring price of keeping coverage. A deductible is an amount you may pay before certain benefits begin. Copayments and coinsurance are your share when you receive care. Compare these together, rather than assuming the lowest premium makes the least expensive plan.

Estimate: annual household premiums + expected medical and prescription cost sharing + other uncovered costs − employer funds actually available and applied to those expenses. Include deductibles within the cost-sharing estimate; do not add them a second time.

Illustration: Plan A costs $180 a month plus $1,800 in expected cost sharing: $3,960 for the year. Plan B costs $300 a month plus $600 in expected cost sharing: $4,200. With those assumptions, Plan A is $240 less expensive. Different care needs could reverse the result. These are hypothetical plans, with no employer funding or other costs assumed.

Run low-use, expected-use, and high-use scenarios in the worksheet. Check what the out-of-pocket limit excludes: premiums and noncovered care can remain your responsibility. Original Medicare alone has no annual out-of-pocket ceiling. A Medicare Advantage medical limit and a Part D drug threshold are separate protections. Even a favorable annual estimate may require cash for a deductible early in the year.

Sources: HealthCare.gov: compare total yearly costs; Medicare: compare Original Medicare and Medicare Advantage.

Read the costs together

Term	What to check
Premium	The amount your household pays to keep coverage. For Medicare, add all applicable components; for Marketplace coverage, use a confirmed quote after any advance credit and revisit it if income changes.
Deductible	What you may pay before specified benefits begin. Check whether medical and drug deductibles are separate and how individual and family amounts work.
Copay / coinsurance	A fixed charge or percentage you pay for covered services. Ask which services have a copay before the deductible.
Out-of-pocket limit	Which covered expenses count, the network rules, and what is excluded. It is not a cap on every dollar your household can spend.

For the high-use scenario, test the plan’s covered in-network limit where applicable, then add premiums and realistic excluded costs. Do not substitute an expected-use estimate for a worst-case budget. If there is no overall cap, acknowledge that uncertainty rather than inventing one.

3. Confirm doctors, hospitals, and ongoing care

Start with the care you would be reluctant—or unable—to change. Check your primary doctor, specialists, hospital, laboratory, mental health providers, and any ongoing therapy or medical equipment. Verify the exact 2027 plan with both the insurer and the provider’s office; “we accept that insurance company” may not identify the right network.

Ask whether the office is accepting patients under that plan and whether referrals or prior authorization are required. If you are in treatment, ask how a change affects authorizations and continuity of care. Request written confirmation where possible and keep the date and representative’s name.

Travelers and people living in more than one state should check routine care away from home separately from emergency coverage. For Original Medicare, confirm that a provider accepts Medicare and ask about assignment. For a managed-care plan, inspect its service area and out-of-network terms. An attractive benefit is useful only if you can access it.

Sources: Medicare: compare Original Medicare and Medicare Advantage.

4. Price your actual prescriptions

Use each medication’s name, dosage, quantity, and refill frequency. Check the plan’s drug list, or formulary, and compare your pharmacy with any preferred pharmacy or mail-order option. Ask about prior authorization, quantity limits, and step therapy—requirements to try a different medicine first. Discuss substitutions with your clinician, not solely with a salesperson.

Medicare readers should review the Annual Notice of Change and compare next year’s plan using their own prescriptions. A plan that suited you this year can change its costs, coverage, or pharmacy arrangements. Use Medicare’s official Plan Finder to compare available options.

For 2027, the Part D out-of-pocket threshold is $2,400 for covered Part D drugs. It is not a limit on premiums, Part B drugs, or all medical spending. The defined-standard Part D deductible is $700, although actual plan designs and assistance can differ. Check the costs of any medication the plan does not cover separately.

Sources: Medicare: your coverage options; CMS: review your Annual Notice of Change; CMS: final 2027 Part D benefit parameters (PDF, Table V-2).

5. Understand the Medicare tradeoffs before switching

There are two main routes for receiving Medicare benefits. Compare the complete coverage arrangement, including any supplemental and prescription coverage, rather than comparing a single advertised premium.

Original Medicare arrangement	What it means for your decision
Potential strengths	Broad access to providers who accept Medicare; generally fewer referral and prior-authorization requirements.
Costs and gaps	Add the applicable Medicare, Medigap, and Part D premiums. Original Medicare alone has no annual spending ceiling; supplemental coverage and eligibility matter.

Medicare Advantage arrangement	What it means for your decision
Potential strengths	One Medicare-approved private plan provides Part A and Part B; most include Part D. Covered medical spending has a yearly limit. Some plans add benefits.
Costs and restrictions	Check the network, authorization rules, medical limits, and extra-benefit restrictions. A $0 plan premium does not generally eliminate the Part B premium.

Sources: Medicare: your coverage options; Medicare: compare Original Medicare and Medicare Advantage.

Check Medigap first. The federal six-month Medigap enrollment period generally starts when you are both 65 or older and enrolled in Part B. It does not restart every fall. Outside protected situations, an insurer may use medical underwriting, charge more, or decline an application; state protections can differ. Before leaving Medicare Advantage, confirm whether you can obtain the Medigap coverage you want, at what price, and when it would begin. Medigap does not supplement Medicare Advantage.

Sources: Medicare: Medigap enrollment protections; Medicare: compare Original Medicare and Medicare Advantage.

Working past 65 or retiring soon? Ask HR how your coverage coordinates with Medicare, which payer goes first, and whether your drug coverage is creditable. Current-employment, retiree, and COBRA coverage do not all provide the same enrollment protections. Confirm the timing before delaying Medicare or changing employer coverage.

Sources: Medicare: working past 65 and coordinating coverage.

If costs are a concern, check Medicare Savings Programs and Extra Help for Part D. For independent assistance with your choices, use your State Health Insurance Assistance Program (SHIP).

6. Protect Medicaid or CHIP—and compare the choices you have

Medicaid and CHIP can provide free or low-cost coverage for eligible households. Medicare and Medicaid are different programs; some people qualify for both and need coordinated help. Eligibility, benefits, and available plans vary by state. If you can choose among managed-care plans, compare participating doctors, prescriptions, and access to the services your household uses. Keeping an existing care team may matter more than a small extra benefit.

Keep your contact information current with the state, read every renewal notice, and supply requested information on time. Being enrolled this month does not eliminate the need to respond to a future notice. Use your official state Medicaid agency for eligibility, renewal, and plan-selection help.

Sources: HealthCare.gov: Medicaid and CHIP applications.

Watch the 2027 changes. New community-engagement requirements generally begin January 1, 2027 (or earlier if a state chooses), for specified adults aged 19–64 in Medicaid expansion/adult-group or certain demonstration coverage. They do not apply to every Medicaid recipient. Exemptions include pregnancy/postpartum status, medical frailty, certain caregiving situations, and other categories. State implementation and notices matter; check whether a requirement applies to you and how an exemption is documented.

Sources: CMS: which adults face Medicaid community-engagement requirements; Medicaid.gov: check eligibility changes in your state.

Federal changes also require six-month eligibility renewals for specified adult populations beginning with renewals initiated on or after January 1, 2027. Do not assume every Medicaid household now renews twice a year. If you receive an adverse notice, ask promptly about review or appeal rights and other coverage. Loss for failing applicable community-engagement requirements does not automatically make you eligible for Marketplace premium tax credits.

Sources: CMS: Medicaid renewal changes and tax-credit restrictions (PDF, pages 8–9).

7. Compare work, Marketplace, and family options

Ask for the Summary of Benefits and Coverage and the Summary Plan Description. Review the employee-only, employee-plus-spouse, and family prices, including any spouse surcharge, network differences, or employer account contributions. If both spouses have work options, price the available combinations using the same assumptions.

One plan for the whole household is convenient, but separate coverage can sometimes fit better. Confirm eligibility and coordination rules rather than assuming everyone must enroll together. An employer coverage offer can also affect Marketplace tax-credit eligibility; check the rules for the employee and family members before counting on a subsidy.

Look beyond the medical plan: dental and vision benefits have their own costs and limits. Verify active-election requirements, dependent documentation, and what happens if you do nothing. Contact HR immediately after a job or household change instead of assuming the annual deadline is your only opportunity.

Sources: Department of Labor: making your health benefits work; IRS: premium tax credits and repayment, including Question 31.

If you are considering Marketplace coverage

Bronze, Silver, Gold, and Platinum describe how a plan and its members share covered costs; they are not quality ratings. A lower premium can come with higher costs when you need care. Compare the network and prescriptions before choosing a metal category.

If you qualify for income-based cost-sharing reductions, you generally must choose a Silver plan to receive those extra savings on deductibles, copays, and coinsurance. A premium tax credit and cost-sharing reductions are different kinds of help. Do not reject Silver based on its headline premium before reviewing the assistance available to your household.

Sources: HealthCare.gov: what plan categories mean; HealthCare.gov: extra savings with Silver plans.

Use the official Marketplace application to check eligibility for assistance. Employer coverage offers and eligibility for other programs can affect the result. Do not assume an offer is unaffordable for every family member just because the family premium is high.

8. Check accounts, contributions, and tax exposure

A health savings account (HSA) can help an eligible person save for qualified medical expenses. For 2027, the regular contribution limits are $4,500 for self-only coverage and $9,000 for family coverage; employer contributions count toward the limit. Eligibility and any catch-up contribution require a separate check. Your own deposit is still your money—not an automatic reduction in the price of care.

Sources: IRS: 2027 HSA limits, Revenue Procedure 2026-24; IRS: HSA and FSA rules (Publication 969).

A large deductible alone does not establish HSA eligibility. New rules also treat certain bronze and catastrophic individual-market plans as HSA-compatible even when they do not satisfy the usual high-deductible health plan (HDHP) design tests. Other eligibility conditions still apply. Check the actual coverage and IRS rules, especially if a spouse’s general-purpose health flexible spending arrangement (FSA) or other coverage could affect eligibility.

Sources: IRS: expanded HSA eligibility, Notice 2026-5 (PDF); IRS: HSA and FSA rules (Publication 969).

Medicare enrollment stops eligibility to contribute to an HSA. When Medicare Part A begins retroactively after delayed enrollment, earlier contributions may also be affected. Ask about your actual Medicare effective date before making or receiving contributions; the timing is not identical for everyone turning 65.

Sources: Medicare: working past 65 and coordinating coverage; IRS: HSA and FSA rules (Publication 969).

For a health FSA, elect an amount based on realistic eligible expenses. Check the employer’s election instructions and whether its plan offers a permitted carryover or grace period. Do not assume unused funds roll over automatically.

Sources: IRS: HSA and FSA rules (Publication 969).

Marketplace shoppers should estimate 2027 household income carefully and report changes promptly. For tax years after 2025, there is no repayment cap on excess advance premium tax credits: you must repay the excess over the credit you actually qualify for. That does not mean everyone repays all their assistance. Self-employment income, retirement income, and household changes make an updated estimate particularly important.

Sources: IRS: premium tax credits and repayment, including Question 31.

9. Confirm the enrollment—not just the application

Before submitting a choice, verify the exact plan name, covered household members, effective date, and payment instructions. Save the confirmation and final documents. If changing coverage, coordinate dates so the replacement begins when intended; do not cancel useful coverage based only on an unconfirmed application.

After enrollment, check the first bill and member information, confirm that any required premium payment was received, and verify access to ongoing care and prescriptions. Resolve inconsistencies with the insurer or administrator promptly. Use official enrollment channels, and do not provide Medicare or financial information to an unsolicited caller simply because the offer sounds urgent.

Your next step: choose two eligible options, gather their 2027 documents, and complete the worksheet below. Set a personal decision date before the official deadline so there is time to resolve missing information. The right comparison is the one that helps you obtain needed care at a cost and level of risk you can manage.

Keep the important dates handy in the CPA at Large calendar.

Make the final choice in this order

• Eligibility and timing: eliminate options you cannot use or that would leave an unintended coverage gap.
• Access: resolve essential doctor, medication, treatment, and network questions before giving cost estimates decisive weight.
• Affordability: compare expected annual spending, a difficult year, and the cash needed early in the plan year.
• Confirmation: keep the acceptance, effective date, payment instructions, and the documents used for your decision.

If you help someone else choose, include them in the discussion and use the program’s authorized assistance process when needed. For Medicare, SHIP offers independent counseling. For Medicaid or CHIP, contact your state agency. For job coverage, ask the benefits administrator to resolve questions in writing.