Around this time of year, you might be wondering, “When is open enrollment?” As it turns out fall is the only time most people can change or sign up for health insurance (otherwise known as the period of “Open Enrollment.”). But here’s the thing: Open Enrollment shouldn’t just be about signing up for the same thing you’ve done in the past. In fact, the decisions you make for your health plan can have a significant impact on your overall financial picture for the entire year. So it’s important to make your decisions around health insurance with care.

Key Questions for Consideration

• Have your anticipated health expenses changed? Are you planning on getting surgery, adding a new member to your family, spending a significant period of the year outside of the country? If so, you may want to consider whether your deductible (the amount you must pay toward health related costs before your insurance kicks in) is optimized. For example, if you expect major medical procedures, a plan with a lower deductible may make sense. You’ll pay a higher monthly premium but that may be offset by having more of your expenses covered. Conversely, a lower premium but higher deductible may make sense if you don’t expect many significant health care expenses.Keep in mind that with every health insurance plan, there are some medical expenses that are covered regardless of your deductible. For example most preventative care (think annual checkups etc.) and a lot of the routine appointments of a newborn baby are typically covered.
• Do you want the ability to contribute to an HSA (Health Savings Account)? Enrolling in a High Deductible Health Plan (HDHP) is typically required in order to be eligible for contributing to a Health Savings Account (HSA). Contributions to an HSA are often called “triple-tax-advantaged” because they:
  • Reduce your taxable income now
  • When invested, grow tax free
  • When withdrawn for medical expenses are tax free (Note: Another great thing about HSA funds is that even when they’re not withdrawn for medical expenses, if you are of retirement age, there is no penalty for withdrawing for other purposes. So while you will be taxed in that circumstance, it would be no different than if you were withdrawing funds from a standard 401(k) or similar. This makes HSA a great retirement savings method.)

Review your plan options carefully and use the tools on your enrollment website to make a decision that’s right for you.

When is Open Enrollment? Key Dates

Now that you know what to be thinking about during open enrollment, when can you get started? Review the table below for general guidelines.

Don’t wait for the new year—start the prep now so you can hit the ground running in 2026!