Oregon Health Insurance Options for Self-Employees and Small Businesses in 2026

If you’re self-employed or running a small business in Oregon, navigating health insurance can feel overwhelming. This guide breaks down health insurance options for self employees, how enrollment works, and what to consider when choosing coverage that fits your budget, business, and health needs.

In May 2025, it was estimated that 16.8 million Americans were self-employed, and many of them rely on individual or small business health insurance to protect their health and income.

Do self-employees need health insurance?

While Oregon does not legally require individuals to carry health insurance, it is strongly recommended to reduce unexpected costs. When you run your own business, your health is directly tied to your ability to earn income and provide for yourself, your team, and family.

Health insurance helps protect you from

• High medical bills due to accidents or illness

• Unexpected financial strain that could disrupt your business

• Gaps in care that may lead to larger health issues later

  
  

When do I need to get health insurance?

You can only enroll in health insurance during Open Enrollment once per year from November 1 to January 15 unless you qualify for a Special Enrollment Period. Qualifying events include:

• Losing employer-sponsored health insurance

• Leaving a job to become self-employed

• Getting married, divorced, or having a child

Special Enrollment Periods usually last just 60 days, so it’s important to act quickly to ensure you don’t miss your opportunity. If you’re transitioning into self-employment, contact us to confirm your eligibility and start enrollment.

Health Insurance for the Self-Employed

The IRS defines self-employment as having a business that has income, but no W-2 employees. Examples include freelancers, independent contractors, Etsy-store operators, mom-and-pop stores, and more.

Once you hire a W-2 employee, you become a small business owner/employer, which opens additional insurance options.

HealthCare.gov, the Oregon Health Insurance “Marketplace”

For most self-employed individuals in Oregon, it’s best to start with HealthCare.gov.

Filling out a Marketplace application on HealthCare.gov will tell you if you are eligible for tax credits, Medicaid, and other cost-savings options. Eligibility is based on your income and household size. 

Although enhanced premium tax credits ceased on December 31, 2025, standard premium tax credits are still available to eligible folks.

See if you qualify for cost-savings

Even if you do not qualify for cost-savings, you can find private health insurance through the Marketplace.

The Marketplace will allow you to choose a health insurance plan that suits your and your family’s needs. Selecting a plan is often the most confusing part. Enrollment assisters and licensed brokers, like Hillock Insurance, are available to guide you through the choices. 

Estimating your income for health insurance when self-employed

You will need to provide your anticipated income for your Marketplace application. Savings are calculated based on your estimated net income for the year you are getting coverage, not the last year. This is great news if you expect lower earnings.

It can be difficult to accurately estimate your net income, especially if you are a new solopreneur. HealthCare.gov advises using your past experience, realistic expectations, industry standards, and other information to make a best guess. 

Update your income in HealthCare.gov as soon as you have more accurate numbers.  Keeping your income estimate current helps avoid repayment surprises during tax season and allows you to fully benefit from available cost-savings. 

Oregon Health Plan (OHP)/Medicaid

Oregon’s Medicaid program is called Oregon Health Plan (OHP) or, for children, Children’s Health Insurance Program (CHIP). Unlike the Marketplace, which you can only enroll in at set times , you can enroll in OHP/CHIP at any time, so long as you are eligible.

Start the application process on HealthCare.gov. A deeper explanation of the Marketplace and OHP is available here.

Other options for getting health insurance when self-employed

You may also get health insurance through:

• Your spouse’s plan: If your spouse is on an employer-sponsored plan that allows dependents, you may join it during the employer’s Open Enrollment or a Special Enrollment Period triggered by you losing your previous coverage.

• COBRA: You may be able to continue your previous employer's health coverage through COBRA for up to 18-36 months. However, COBRA is quite expensive so, it is typically advised to explore other options first.

• Medicare: If you are over the age of 65 or have a qualifying disability, you should get health insurance through Medicare. Contact a local agent like Hillock Insurance for help enrolling or changing Medicare plans.

• Short-Term Health Insurance: These are temporary health insurance plans for up to 12 months. They often have limited coverage and aren’t a great fit for those with pre-existing conditions.

The best choice for you will often come down to cost, coverage, and flexibility.

What are my health insurance obligations as a small business owner?

Oregon only requires employers to offer health insurance to employees and dependents once they have fifty or more full-time employees. However, small business owners have a couple of options to insure themselves and offer coverage to their team, if they choose. 

Note: Workers comp, a separate type of insurance, is required even if you only have one employee.

Option 1: Enroll in Small Business Health Insurance

Small businesses can offer group health insurance, which may be more affordable than individual plans and can be a valuable employee benefit. These plans must be purchased through a licensed broker and require coordinating enrollment with your team.

Option 2: Encourage employees to get a plan through the Oregon Health Insurance Marketplace

If you are not offering health insurance, you can still support employees by:

• Informing them of how to enroll through HealthCare.gov when they start working for you – share this guide as a free resource!

• Reminding them about Open Enrollment each fall.

Frequently Asked Questions

How do I get health insurance as a self-employee?

Most self-employed individuals start with HealthCare.gov to check eligibility for tax credits, Medicaid, or private health insurance plans. Hillock Insurance can also walk you through your health insurance options in Oregon.

How do I lower my health insurance costs?

You may qualify for premium tax credits, cost-sharing reductions, or a self-employed health insurance tax deduction. Updating income estimates is key.

Can I deduct health insurance premiums if I’m self-employed?

In many cases, yes. Self-employed individuals may be able to deduct health insurance premiums as an adjustment to income. Consult a tax professional for specifics.

What happens if my income changes during the year?

You should update your income on HealthCare.gov as soon as possible. This helps prevent overpayment of tax credits and unexpected tax bills.