It’s that time of year again—open enrollment season. If you’ve ever felt a little overwhelmed trying to choose the right benefits, you’re definitely not alone. Between health plans, savings accounts, and all the fine print, it can feel like a lot to sort through.
But don’t worry, I’ve got you covered. Whether you’re a seasoned pro or it’s your first time making these decisions, a few simple tips can help make the process way easier (and maybe even a little less stressful).
Let’s dive in and get you set up for a smooth enrollment experience.
Open Enrollment Tips
Open Enrollment Tip #1: Mark Your Calendar!
Open enrollment times vary greatly but typically occur during the months of October through December. For those who participate in Medicare, Federal Employee Health Benefits (FEHB), or the Health Insurance Marketplace, here are some key dates for 2026 enrollment:
- Medicare open enrollment: October 15, 2025 – December 7, 2025; changes take effect on January 1, 2026
- Open enrollment for Federal plans: November 11, 2025 – December 9, 2025; changes take effect on the first full pay day in January 2026
- Health Insurance Marketplace (or ACA) open enrollment for individual plans: November 1, 2025 – January 15, 2026. Enroll by Dec. 15 for coverage to start on January 1; any enrollments between December 16 – January 15 will start on February 1.
- State-specific open enrollment plan dates may vary.
If you are still waiting to hear from your HR department or plan provider, please ask when you’ll receive the information.
Open Enrollment Tip #2: Review Prior Benefits Usage
Review how you used your benefits last year to help estimate what you’ll need next year. Check for changes in your plan’s:
- Provider network
- Monthly premiums
- Deductible
- Co-insurance, and
- Out-of-pocket maximum
But in case I confused you with these terms, here’s a quick reminder:
- Network: Plan-approved doctors and other healthcare professionals. You usually pay less to receive care from these providers.
- Premium: Your monthly payment for your health plan. A subsidy may offset some of the premium cost if you qualify.
- Deductible: The amount you pay out-of-pocket before your insurance starts covering part of your medical bills.
- Co-insurance: After you meet your deductible, this is the percentage you pay until you hit your out-of-pocket max.
- Out-of-pocket maximum: The most you’ll pay in a year before you plan covers 100% of covered services.
Open Enrollment Tip #3: Explore New Benefit Options
Life changes (such as marriage, having a child, or planning for retirement) can affect your future needs and financial goals.
That’s why it’s important to review all of your benefit options each year.
Even if your employer adjusts offerings or shifts more costs to you, you may still have opportunities to:
- Enroll in new account types (like HSAs or FSAs) to save on taxes
- Choose plans that better match your current needs
- Prepare for future expenses with smarter savings tools
So don’t just renew last year’s choices. Take time to explore what’s new and what’s changed.
Open Enrollment Tip #4: Sign up for FSA or HSA Benefits
Many employers offer tax-advantaged healthcare benefit accounts to help employees save on out-of-pocket costs. These may include:
- Flexible Spending Accounts (FSA) – Use pre-tax dollars for medical costs like co-pays, prescriptions, and deductibles.
- Health Savings Accounts (HSA) – Similar to an FSA, but only available if you’re enrolled in a High Deductible Health Plan (HDHP). You can also use it for COBRA premiums and save long-term.
- Health Reimbursement Arrangements (HRA) – Funded exclusively by your employer to help cover medical expenses, and it’s not counted as taxable income.
Other benefits for non-healthcare expenses include:
- Dependent Care FSAs for child and dependent care
- Transit/Commuter accounts for commuter fare and transportation expenses.
Open Enrollment Tip #5: Get Organized
Before you start choosing your benefits, it’s important to gather your healthcare receipts and Explanation of Benefits documents from the previous year. Doing so will help you make informed decisions about insurance plan needs, FSA or HSA options, and contributions.
Pro tip:
Keep your paperwork in one place and consider using a benefits debit card. It makes paying for eligible expenses easier and reduces the need for manual reimbursement claims.
Remember these tips for easy enrollment, or check out this helpful video: