Hi there.
Open Enrollment means three completely different things depending on where your coverage comes from. It's the sign-up period for next year’s health coverage.
If you’re on Medicare you can join or leave an Advantage Plan (Part C), or make changes to your prescription drug coverage (Part D). It’s open now (October 15th – December 7th, 2026).
For those of us who are still working, employers typically build their plans on a calendar year, which means that the sign-up window lands in the fall. Check with HR before assuming when the window is.
For people purchasing health insurance through the Marketplace (ACA), it’s very similar with a window that opens on November 1st.
In every case, it means sign-up is open, and you can make changes without a reason. Outside the window, you need a qualifying event (like a change in your family or employment).
The window exists to make sure that people aren’t just waiting until they’re sick to apply for coverage. Since the ACA was introduced, healthcare insurers on the Marketplace (and group health plans) can no longer limit applicants on the basis of prior medical conditions. Insurance works because the costs are reduced by healthy individuals sharing some of the costs of those with expensive care needs. Hence, the window of application.
Now that we’ve addressed what it is, how do you make sure you make the right decision? It’s common to compare the costs and stop there, but it’s important to take a look at some of the finer details: deductibles and out-of-pocket maximums; in-network coverage; HSA eligibility; changes to income; household changes – job, kids moving out, a marriage. Let’s break them down one by one.
The deductible is the amount that you are responsible to pay before the insurer will step in and cover any costs. After that annual deductible has been met, the insurer will cover a percentage of the costs depending on your plan tier (bronze, silver, gold, platinum). Some plans give each person their own deductible, others apply a single family amount, and it’s worth confirming. Plans have an annual limit you’re on the hook for, called the out-of-pocket maximum. Once you hit it, the plan pays for covered services the rest of the year.
Being sure your emergency fund has at least enough to cover your out-of-pocket maximum is essential. This is what you're on the hook for if it rains, and it can rain. If you're unable to cover that, consider a different plan with a lower maximum to make sure you and your family are protected.
Do you have a doctor you've worked with for years? Double check that they're still considered in-network for your new plan. Oftentimes providers change who they accept based on ease of claims or flat out simplicity. If sticking with your primary care provider is important, be sure to check before you make changes. A phone call usually gets you enough to know if they'll be accepting that coverage for the foreseeable future.
Are you funding an HSA? As of January 2026, every bronze and catastrophic plan on the Marketplace counts as HSA-eligible. An HSA has a tax advantage you won’t find anywhere else: the money goes in untaxed, grows untaxed, and comes out untaxed when you spend it on qualified medical expenses (otherwise you’ll owe tax and a penalty). This is all federal treatment, and a few states don’t follow it. One thing some people don’t know: there’s no deadline for paying yourself back. If you have a qualified expense today and pay it out of pocket, you can reimburse yourself from the HSA years later, as long as the expense happened after the account was opened and you’ve kept the records. Be sure you’re eligible to contribute – a qualifying plan is only half of it, and things like a general-purpose FSA can disqualify you.
Did you recently lose your job, get a promotion or change jobs entirely? On the Marketplace, your income decides what you pay, but not the way most people assume. The plan’s price doesn’t change. What changes is how much of the premium gets paid on your behalf, straight to the insurer, as an advance on a tax credit that’s yours. If you experience a large pay raise or bonus mid-year, and you're already on an ACA plan, be aware that you might be responsible for the difference when you file your taxes next year.
Did the dependents in your household change? Changes to the number of dependents directly impact tax credit eligibility. Remember that when you review your enrollment for next year.
The most important thing is to review all your available options and not wait until the last minute to make a split decision. Just because a plan was right for you when you signed up three years ago doesn’t necessarily mean you should sign back up with the same one.
What’s your biggest priority when it comes to picking a plan?
Until next time, God Bless.
Ian
Educational content provided by Entrusted Stewardship LLC. This material is for general education only and is not individualized investment, tax, or legal advice. No specific investment, insurance, or tax strategy is recommended or endorsed here. Consult your CPA, attorney, or advisor regarding your specific situation.
