Open enrollment: a midlife checklist for choosing next year's coverage

Know your dates

HealthCare.gov lists November 1 as the start of open enrollment for 2027 coverage and January 15 as the end. To have coverage begin January 1, you must enroll and pay your first premium by December 15; enrolling between December 16 and January 15 starts coverage February 1. Some states run their own marketplaces and may set different dates, so check your state's site if it is not HealthCare.gov.

Medicare's open enrollment runs from October 15 to December 7, with changes taking effect January 1. If you are already in a Medicare Advantage plan, there is a second window from January 1 to March 31 to switch plans or return to Original Medicare.

Employer plans usually hold open enrollment in the fall, but dates and rules vary. Missing your window generally means waiting a year unless you have a qualifying life event such as marriage, a move or losing other coverage.

Why midlife changes the math

In your 20s and 30s, the cheapest premium is often the right choice. After 40, many people start using more care: regular prescriptions, specialist visits, screening tests such as colonoscopy and mammograms, imaging and lab work. A plan with a low premium but a high deductible and narrow network can end up costing more.

Look at what you actually used this year and what you expect next year. If you are planning a procedure, starting a long-term medicine, or managing a condition like high blood pressure, diabetes or menopause symptoms, those costs should drive the decision.

Your checklist before you choose

• Prescriptions: is each medicine on the plan's formulary, and at what tier? Does it need prior authorization?
• Doctors and specialists: are your current clinicians in network? What about the nearest specialists you might need?
• Total cost, not just premium: add the premium, deductible, copays and coinsurance for the care you expect.
• Out-of-pocket maximum: the most you would pay in a bad year.
• Preventive care: screenings recommended for your age are often covered without cost-sharing in many plans, but confirm.
• Telehealth and mental health benefits.
• Lab and imaging coverage, and whether you must use specific labs.

Weight-loss medicines and other specific needs

If you are using or considering a GLP-1 medicine for weight, check carefully. Coverage for weight-management drugs varies widely, often requires prior authorization and documentation, and may differ from coverage for the same drug used for diabetes. Do not assume this year's coverage continues next year.

The same goes for hormone therapy, testosterone and other ongoing treatments. Look up the specific product and strength, not just the drug class.

HSA-eligible plans and FSAs

Open enrollment is also when many people choose whether to contribute to a health FSA or move to an HSA-eligible high-deductible plan. For 2026, the IRS health FSA contribution limit is $3,400. FSAs are generally use-it-or-lose-it, so elect an amount you are confident you will spend.

An HSA requires enrollment in a qualifying high-deductible health plan, and its balance rolls over indefinitely. For people who are relatively healthy and can afford the deductible, an HSA can be a useful long-term tool. For people with predictable, significant medical costs, a lower-deductible plan may work out better. Run both scenarios.

Questions worth asking your benefits team

• Is our health FSA offering a grace period, a carryover or neither next year?
• Does the employer contribute to the HSA, and how much?
• Which plans include my current doctors and nearest hospital?
• How are specialty drugs and weight-management medicines handled?
• Is there a separate deductible for prescriptions?
• What wellness, fertility, menopause or mental health benefits are included?

Where HealifyMD fits

HealifyMD publishes its prices, and prices are confirmed at your eligibility review. Whether you can use FSA or HSA funds for a particular service depends on your plan and IRS rules. Our lab panel can help you understand your risks before you choose coverage, for example if you want to know your blood sugar, cholesterol or hormone status before deciding how much care to budget for next year.