Your guide to open enrollment: Dos and don’ts for small businesses
The annual open enrollment period began on November 1, 2026 and ends on January 15, 2027 for small business owners and self-employed individuals who access health insurance through the individual marketplace. A lot is changing in health insurance this year, from rising premiums, to lapsed subsidies, to new work requirements as changes from H.R. 1 go into place.
This is the time of year when entrepreneurs and small business employees can make changes to their healthcare plans, re-enroll or renew their plans. Below are some key tips and best practices to keep in mind during open enrollment.
Do: Enroll early
If you wish to receive healthcare coverage starting January 1, 2027, you must select a plan by December 15, 2026! The following states have different open enrollment windows:
- California: November 1, 2026 – January 31, 2027
- Connecticut: October 23, 2026 – January 15, 2027
- Idaho: October 15, 2026 – December 15, 2026
- Massachusetts: October 23, 2026 – January 23, 2027
- New Jersey: November 1, 2026 – January 31, 2027
- New York: November 1, 2026 – January 31, 2027
- Rhode Island: November 1, 2026 – January 31, 2027
- Vermont: November 1, 2026 – December 28, 2026
- Virginia: November 1, 2026 – January 29, 2027
- Washington, DC: November 1, 2026 – January 31, 2027
Do: Check if your state has an individual marketplace
No matter where you live, small business owners, their employees and solo entrepreneurs will be able to access quality health coverage. Although many individuals may be able to enroll in health insurance plans through healthcare.gov, some states run their own marketplaces and setup may change from year to year. Be sure to check which marketplace serves your state by going directly to healthcare.gov.
Do: Have your ID ready and book help early
There are new rules that apply to anyone enrolling with an agent through HealthCare.gov:
- You’ll have to approve your agent electronically. You’ll get a one-time code by text, email or phone to authorize the agent.
- “Higher-risk” applicants must verify their identity through a service like Experian before authorizing an agent. That includes first-time applicants, people moving states, people switching agents and anyone paying $30 a month or less.
- Agents who are new to the marketplace can’t help with 2027 enrollment until February at the earliest, so appointments may fill up fast.
Do: See if you or your employees qualify for Medicaid
Forty-one states (including Washington, DC) have expanded Medicaid coverage, which can provide free or low-cost coverage for eligible individuals. Many small business owners and employees qualify for this expanded coverage, but Medicaid eligibility varies by state. Find out more about Medicaid eligibility and what to do if your state hasn’t expanded Medicaid.
Additionally, in 2027, adults who lose Medicaid for not meeting new work requirements can’t get subsidized marketplace plans, and may qualify for a special enrollment period to get marketplace coverage
Do: Visit the Healthcare.gov website to learn about additional credits, eligibility criteria and more
You may qualify for additional credits and healthcare savings. To get an estimate on extra savings, learn about eligibility criteria and much more, visit healthcare.gov.
Don’t: Forget to check if you can access healthcare through the individual marketplace
If you expanded your business in the last year and hired more full-time employees, you may be required to purchase small group coverage for yourself and employees through a broker. Learn more about your healthcare plan options.
Don’t: Let your plan auto renew without comparing
Insurers have proposed a median 15% rate increase for 2027; however, this rate varies vastly from state to state, with some premiums increasing by more than 50%. Additionally, you may see changes in what is offered on the marketplace this year—notably Cigna is exiting the individual marketplace. If your premiums have risen, you may want to shop around for another plan. The out-of-pocket maximums are rising to $12,000 for an individual and $24,000 for a family. Make sure you are not only comparing premiums, but also deductibles.
Don’t: Skip healthcare enrollment
While it may seem like an easy way to save money, skipping healthcare coverage may put you in a financial bind. Having health insurance helps protect both your health and financial wellbeing by ensuring you’re protected against an unexpected healthcare scare and might make a difference between staying healthy and keeping your business. Depending on where you reside or where you operate your business, you may get a penalty for not having health insurance.
Additionally, be wary of ‘junk insurance’ plans that may seem like flexible, budget-friendly alternatives to comprehensive coverage, but in reality are not required to adhere to the same consumer protections as Marketplace plans, leaving you vulnerable.
Don’t: Forget about the Special Enrollment Period
A Special Enrollment Period (SEP) is available to people with qualifying events, such as losing health coverage. Depending on the SEP type, you may have up to 60 days to enroll in a plan. Learn more about SEP.
Don’t: Fall for enrollment scams
This year, the federal government canceled about 760,000 enrollments that brokers had signed people up for without their knowledge. Brokers are now banned from offering cash incentives, promising guaranteed $0 premiums or giving fake deadlines.
Some agents also sell plans outside the marketplace, including short-term or limited plans that may not cover pre-existing conditions and don’t qualify for tax credits. If you want a marketplace plan, say so up front, and ask whether any plan you’re offered is ACA-compliant.
Don’t: Go it alone
Insurance brokers, health enrollment navigators and unbiased groups can help you compare plans and handle the enrollment process at no additional cost. You can find local assistance near you.
Have a healthcare story to share?
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