Open Enrollment Checklist: Choose Your Health Plan for 2027
Open enrollment is the one time each year when you can change your health coverage without a special reason, and it goes by fast. This open enrollment checklist walks you through the dates, the numbers that matter and a simple way to compare plans side by side, so you can choose coverage for 2027 calmly instead of clicking "renew" at midnight.
Key takeaways
- In most HealthCare.gov states, enroll by 15 December 2026 for coverage that starts on 1 January 2027. State-run marketplaces and employers can set different dates.
- Compare the full cost of a plan, not just the premium: deductible, out-of-pocket maximum, copays, coinsurance and drug coverage all count.
- Check that your doctors, hospitals and prescriptions are covered before you switch.
- If a plan is HSA-eligible, factor in the tax-advantaged savings account that comes with it.
Whether you buy your own coverage as a freelancer, choose a plan through your employer or pick benefits for your small team, the decision follows the same pattern. You gather a few facts about how you used care this year, line up two or three plans, and test each one against your real life. That is what this guide helps you do.
A quick note before we start: this article is general information about health coverage, not insurance, tax or medical advice. Plan rules vary, so read the official plan documents and talk to a licensed insurance agent, a benefits adviser or a tax professional about your own situation.
Know your open enrollment deadlines
The biggest open enrollment mistake is simply missing the window. Here are the dates to put in your calendar now.
- HealthCare.gov (US Marketplace). Open enrollment for 2027 coverage started on 1 November 2026. In most HealthCare.gov states, you need to enroll by 15 December 2026 for coverage that starts on 1 January 2027.
- State-run marketplaces. Some states run their own marketplace and can set different deadlines. Check your state's site rather than assuming the federal dates apply.
- Employer plans. Each employer sets its own open enrollment window, and it is often only a few weeks in the fall. Look for an email from HR or a notice in your benefits portal, and note the closing date.
If you miss open enrollment, you usually have to wait until next year unless you have a qualifying life event. Changes such as moving, getting married, having a baby or losing other coverage can open a special enrollment period. Keep that in mind if your life is about to change in the next few months.
Pro tip
Set two reminders: one a week before your deadline to make a decision, and one two days before to confirm you actually submitted it. Save the confirmation page or email in a folder called "Health plan 2027".
Gather what you need before you compare
Comparing plans is far easier when your information is in one place. Spend 20 minutes collecting these items first.
- This year's medical use. Count doctor visits, specialist visits, urgent care or emergency trips, lab work and any planned procedures. Your insurer's online portal often lists claims.
- Your prescriptions. Write down every regular medicine, the dose and how often you fill it.
- Your providers. List the doctors, specialists, hospitals and pharmacies you want to keep.
- Household details. Who needs coverage next year, and is anyone aging off a parent's plan, starting a new job or expecting a baby?
- Income estimate. If you buy through the Marketplace, your expected household income for 2027 affects the help you may get with premiums, so make a careful estimate.
- Your current plan summary. Have this year's plan details to hand so you can see what is changing.
Freelancers with uneven income should note that the Marketplace asks for an estimate. Base it on your realistic expectations and update it if your income changes during the year.
The numbers that decide what a plan really costs
A low monthly premium can hide a high bill later. To compare fairly, look at every cost a plan can charge you.
Premium
The amount you pay every month just to have the coverage, whether or not you use it. Multiply by 12 to get the yearly figure.
Deductible
What you pay for covered care before the plan starts sharing costs. Some services, such as many preventive visits, may be covered before you meet it. Check the plan summary.
Copays and coinsurance
A copay is a set amount for a visit or prescription. Coinsurance is your percentage share of a bill after the deductible. Both add up if you see doctors often.
Out-of-pocket maximum
The most you would pay for covered, in-network care in a plan year. After you reach it, the plan pays 100% of covered costs for the rest of the year. This is your worst-case number, so it deserves a close look.
Network and prescriptions
A plan is only good value if it covers the care you actually use. Search each plan's provider directory for your doctors and hospitals, and check the drug list (often called a formulary) for each prescription. Note which tier each drug sits in, because that changes what you pay.
Common mistake
Picking the plan with the lowest premium without checking the network. If your main doctor or a regular specialist is out of network, the savings can disappear after one or two visits. Always confirm providers before you enroll, and call the office if the directory is unclear.
How to compare plans step by step
Once your information is ready, use this simple method to compare two or three plans.
- Shortlist plans. Choose two or three plans that cover your key doctors and prescriptions. Drop any plan that fails this test.
- Add up the yearly premiums. Monthly premium times 12, for each plan.
- Estimate a normal year. Using your list of visits and prescriptions, estimate what you would pay in copays, coinsurance and deductible.
- Estimate a bad year. Add the yearly premiums to the out-of-pocket maximum. This shows the most each plan could cost you.
- Factor in tax-advantaged accounts. If a plan is HSA-eligible, note what you could save into an HSA. If your employer offers an FSA, note that too.
- Pick and confirm. Choose the plan that fits both your normal year and a bad year you could live with, then submit and save the confirmation.
A simple plan comparison template
Copy this table into a spreadsheet and fill in one row per plan. The amounts below are made up for illustration only.
| Plan | Yearly premium (example) | Deductible (example) | Out-of-pocket max (example) | Doctors in network? | Drugs covered? | HSA-eligible? |
|---|---|---|---|---|---|---|
| Plan A (Silver PPO) | $4,800 | $2,000 | $7,000 | Yes, all | Yes, tier 2 | No |
| Plan B (HDHP) | $3,600 | $3,500 | $7,500 | Yes, all | Yes, tier 2 | Yes |
| Plan C (Bronze HMO) | $3,000 | $6,000 | $8,500 | Main doctor only | Tier 3 | No |
Add two extra columns for "normal year total" and "bad year total" and the right choice often becomes obvious.
Hypothetical example
Imagine Jordan, a freelance web developer who is generally healthy, sees a doctor twice a year and takes no regular medicine. Using the made-up numbers above, Plan B costs $1,200 less in premiums than Plan A. In a bad year, Plan B's total is $3,600 plus $7,500, or $11,100, while Plan A's is $4,800 plus $7,000, or $11,800. Plan B also lets Jordan save into an HSA. For Jordan, the HDHP looks like the better fit. Someone with frequent specialist visits might reach the opposite answer, which is exactly why you run your own numbers.
HSA-eligible plans: what to check for 2027
A health savings account (HSA) pairs with an HSA-qualified high deductible health plan (HDHP). Money you put in is yours, it rolls over every year, and it stays with you if you change jobs. That makes an HDHP worth a careful look if you are fairly healthy or can cover a higher deductible from savings.
For 2027, a plan needs a minimum deductible of $1,750 for self-only coverage or $3,500 for family coverage to qualify as an HDHP, and its out-of-pocket maximum can be no higher than $8,700 for self-only or $17,400 for family coverage. For comparison, the 2026 HSA limits are $4,400 and $8,750. These figures change each year, so check IRS.gov for updates.
Before choosing an HDHP, ask yourself whether you could pay the full deductible if something happened in January. If the honest answer is no, start an HSA or emergency savings cushion early, or consider a plan with a lower deductible.
If your employer offers an FSA
A health flexible spending account (FSA) lets you set aside pre-tax money for medical costs through your employer. The 2026 health FSA limit is $3,400. As of late October 2026, the IRS had not yet announced the 2027 limit, so check your enrollment materials for the figure your plan uses. FSAs are generally use-it-or-lose-it, so choose an amount based on costs you are confident you will have. If you pay for childcare, a dependent care FSA has a limit of $7,500 per household from 2026.
Notes for small business owners and UK readers
If you run a small business, open enrollment is also a good moment to talk with your team. Share the deadline early, explain where to find plan documents and give people time to ask questions. A short, friendly reminder email a week before the window closes helps everyone.
In the UK, the NHS covers residents, so there is no open enrollment in the US sense. Private medical insurance is optional and is often offered as an employer benefit. It is usually a taxable benefit in kind, so check your payslip or ask your employer how it is treated before you sign up, and read the policy exclusions carefully.
Your open enrollment checklist
- Find your deadline: HealthCare.gov, your state marketplace or your employer
- List this year's visits, prescriptions and planned care
- Write down the doctors, hospitals and pharmacies you want to keep
- Estimate your 2027 household income if you use the Marketplace
- Shortlist two or three plans that cover your providers and drugs
- Compare premium, deductible, copays, coinsurance and out-of-pocket maximum
- Work out a normal year total and a bad year total for each plan
- Check HSA or FSA options and decide how much to contribute
- Submit before the deadline and save the confirmation
Frequently asked questions
What happens if I do nothing during open enrollment?
It depends on where your coverage comes from. Some plans renew automatically, but your premium, network or benefits may change, and some employers require you to re-enroll in certain benefits such as an FSA every year. Always read the renewal notice and actively confirm your choice.
Can I change plans after open enrollment ends?
Usually only if you have a qualifying life event, such as moving, getting married, having a baby or losing other coverage. That can open a special enrollment period. Otherwise, you generally wait until the next open enrollment.
Is a high deductible plan a good idea?
It can be if you are generally healthy and can afford the deductible from savings, because the lower premium and the HSA can add up. It can be a poor fit if you expect frequent care or could not cover the deductible. Run both a normal year and a bad year before you decide.
Do I need to pick the same plan as my spouse?
Not always. Some households compare a family plan with each person taking their own employer's plan. Check the costs and rules for each option, including how dependents are covered, before you decide.
Related reading
The bottom line
Open enrollment rewards a little preparation. Note your deadline, list the care you used this year, confirm your doctors and drugs, and compare plans on their full yearly cost in both a normal year and a bad one. If an HSA-eligible plan or an FSA fits your situation, plan your contributions at the same time.
Block out an hour this week, fill in the comparison table and submit your choice well before the deadline. Your future self, opening a medical bill in March, will be glad you did.
