Seven Tips for Conquering Open Enrollment

Open enrollment is your annual opportunity to choose your benefits that protect your health and finances. Smart decisions now can save you money and ensure you get better care when you need it most.

Here are seven tips for making open enrollment season as low-stress and successful as possible.

#1: Start Early and Stay Organized

Don’t wait until the last minute to review your benefit options. Open enrollment periods are usually short and vary by provider. Yet rushing through important decisions can lead to costly mistakes.

Depending on where you get your insurance from, open enrollment isn’t the same for everyone:

• Do you enroll through your employer? Most businesses select two to three weeks between September and December when you can review and sign up for health benefits for the following year.
• If you buy through a state exchange or federal health insurance marketplace, open enrollment runs from November 1 to January 15 each year.
• Open enrollment runs from October 15 to December 7 each year for people who enroll in Medicare.

Most plan years begin January 1, though your plan may have a different start date.

Mark your calendar as soon as you get your enrollment materials and set aside dedicated time to review your options without distractions. Starting early gives you time to research, ask questions, and make informed choices.

#2: Look At Your Current Situation

Before looking at new options, reflect on how your current benefits worked this year.

• What did you like about your coverage?
• Were there any gaps or surprises?
• Did you use all the benefits you paid for?

Tracking your healthcare deductibles can help you make better decisions at open enrollment time. Know the following:

• The total amount of your deductibles
• The date your deductible starts over
• What expenses don’t count towards your deductible
• If you have different deductibles for in-network and out-of-network
• How often do you meet your deductible

Use last year’s healthcare receipts and Explanations of Benefits (EOBs) to assess your coverage and spending. They can also help you assess your other benefit needs, like signing up for a Flexible Spending Account (FSA) or Health Savings Account (HSA).

And finally, think about any changes in your life since last year. Major life events, such as marriage, divorce, having a baby, or changes in your health, can significantly impact which benefits you choose. Your needs may be different this year than they were in the past.

#3: Make Smart Health Insurance Choices

Health insurance is typically your largest benefit expense, so it deserves careful attention. Don’t just focus on monthly premiums! Add up your total yearly costs, including deductibles, copays, and out-of-pocket limits. Doing so can help you decide between a lower-premium, high-deductible health plan and a higher-premium plan with co-pays for commonly used healthcare services. For example, if you’re generally healthy and don’t visit the doctor often, a high-deductible health plan with a Health Savings Account (HSA) could be a great option.

HSAs offer triple tax benefits:

• Your contributions reduce your taxable income
• The unused money in your HSA account grows tax-free through interest income and investing, and
• You can withdraw tax-free funds in any amount at any time to pay qualified medical expenses

However, if you have ongoing health needs or take regular medications, a plan with higher monthly premiums but lower costs when you access care (such as going to the doctor or getting a prescription filled) may save you money overall.

Many insurance companies offer online tools to help estimate your total annual costs.

#4: Don’t Forget the Supporting Benefits

Health insurance gets most of the attention, but other benefits matter too.

• Dental insurance might seem optional until you need major work.
• Vision coverage can save you hundreds on glasses or contacts each year.
• Life insurance through your employer is often more affordable than buying coverage on your own.
• Disability insurance is another valuable benefit that many people overlook. If an illness or injury prevented you from working, disability coverage could help replace a portion of your income.

#5: Maximize Your Tax-Advantaged Savings

Open enrollment is also your opportunity to set up tax-advantaged accounts that can save you money.

• Flexible Spending Accounts (FSAs) let you pay for qualified medical expenses with pre-tax dollars, reducing your taxable income. And unlike an HSA, you don’t need a special health plan to use one. The amount you can set aside each year in an FSA account is set by the IRS; for 2026, it is $3,400.
• Health Savings Accounts (HSAs) The IRS maximum contribution limits for HSAs in 2026 are $4,400 for individuals and $8,750 for families. Employees age 55 and older may make an additional $1,000 “catch-up” contribution.
• Health Reimbursement Arrangements (HRAs) If your employer offers an HRA, the company funds the account and determines how you can spend the money. However, an HRA does not count towards your income; in that sense, it is also tax-free.
• Dependent Care Assistance Plans provide significant tax savings for parents and adult children by letting you pay for day care, summer day camp, and before- and after-school care with pre-tax dollars. Like healthcare FSAs, the IRS sets the amount you can set aside. For 2026, that amount is $7,500.

There are some key differences in these account options.

• To enroll in, and contribute to an HSA, you must enroll in a qualified high-deductible health plan. With an HSA, you are the account owner. You don’t have to forfeit the account if you change employers or retire.
• FSAs do not have the same deductible requirements as HSAs. Your employer owns the FSA. If you leave your employer (either voluntarily or involuntarily), you cannot take the FSA with you or continue to use the funds.
• You cannot have a health FSA account and an HSA account at the same time.

You can make contributions to both types of accounts in the form of pre-tax withdrawals from each paycheck. Depending on plan setup, employers can make contributions to an HSA, if the combined employer/employee contributions do not exceed maximum limits. Employers can also contribute to their employees’ FSAs, either matching employee contributions dollar for dollar or setting an annual limit of $500.

FSAs and HSAs differ when it comes to dealing with unspent funds at the end of the plan year. Typically, FSA funds need to be exhausted completely or face possible forfeiture. However, many plans allow you to roll funds over to the next calendar year. Some FSAs have a grace period of up to 2.5 months after the plan year ends for you to use unspent dollars. Keep this in mind when deciding how much to contribute to your plan.

HSAs do not have a use-it-or-lose-it deadline. Unspent funds can remain in your account for as long as you wish, which makes HSAs an excellent tool for supplementing retirement plans.

Ask if your employer’s plan offers a benefits debit card. Using one may reduce the number of receipts you must file for reimbursement.

#6: Use the Help That’s Available

You don’t have to navigate open enrollment alone. Most employers provide helpful resources, such as benefits fairs, information sessions, and online tools. Many companies also offer one-on-one consultations with benefits specialists.

Don’t hesitate to ask HR questions about anything that’s unclear. Whether you want to understand network coverage, prescription costs, or how different scenarios might affect your expenses, asking questions now can prevent unpleasant surprises later.

Beneliance clients and their employees have access to numerous tools and resources on our website, including The Adventures of Captain Contributor benefits education program.

#7: There Really Isn’t a “One Size Fits All” Plan

Remember that there’s no one-size-fits-all approach to benefits. The best package for you depends on your health needs, family situation, and financial goals. A single person in their twenties will have different priorities than a parent of three or someone nearing retirement.

Consider both your current needs and what might change during the year. If you’re planning to start a family, you’ll want strong maternity coverage. If you’re managing a chronic condition, prescription drug coverage might be your top priority.

Conquering Open Enrollment: Final Thoughts

Open enrollment is your annual opportunity to create a benefits package that truly works for your life. While it requires some time and attention, making informed decisions can provide significant financial protection and peace of mind.

Take the process seriously, but don’t let it overwhelm you. With proper planning and the right resources, you can build coverage that protects your health, supports your family, and fits your budget. The decisions you make now will affect your financial well-being throughout the entire year, making your time investment well worth it.

Beneliance has been serving employers and their hard-working employees with FSA, HSA, HRA, and COBRA, and administration since 1996.