The 2016 Aflac WorkForces Report found that 57% of employees spent less than 30 minutes making their open enrollment choices. That number has almost certainly not improved in the decade since. Most people click through the same selections as last year, pick the plan with the lowest premium, and move on.
That approach can cost thousands of dollars. The right health plan for your situation, the right FSA or HSA contribution, the right supplemental coverage decisions, these aren’t obvious without asking specific questions first. And open enrollment is often the only time of year you can change them.
Here’s what to actually ask before you lock in your benefits.
First: What Changed From Last Year?
This is the question most people skip, and it’s the most important one. Your employer’s plans change every year. Premiums go up. Deductibles shift. Networks change. A plan that was right for you last year may not be right this year, and the plan that’s right this year may not be the same one.
According to the Kaiser Family Foundation’s 2025 Employer Health Benefits Survey, average family premiums reached $26,993 in 2025, a 6% increase that outpaced wage growth of 4%. That means the math of your health plan comparison almost certainly changed from last year even if nothing else in your life did.
Before evaluating any plan, ask your HR department or benefits team specifically: what changed from last year? Look for increases to premiums, deductibles, copays, and out-of-pocket maximums. Look for changes to the provider network. And look for any new plan options or eliminated options that weren’t available before.
What Is My Actual Out-of-Pocket Maximum?
Most people focus on the monthly premium when comparing health plans. The premium is the most visible cost, but it’s often not the most important one for your actual financial exposure.
The out-of-pocket maximum is the most you will pay for covered services in a plan year before your insurance covers 100% of remaining costs. For a family, this number can be $8,000, $12,000, or higher depending on the plan. That’s your worst-case scenario for a year with significant medical expenses.
According to Included Health’s open enrollment guide, it’s not just about the lowest premium or deductible. You need to understand what your total financial exposure looks like under each plan option across realistic scenarios. A plan with a lower monthly premium but a $10,000 out-of-pocket maximum exposes you to much more financial risk than a plan with a higher premium and a $5,000 out-of-pocket maximum, if you have a year with significant medical needs.
The questions to ask: what is the out-of-pocket maximum for each plan option, for both individual and family coverage? How does that number compare to the premium savings of choosing a lower-cost plan?
Are My Doctors and Prescriptions Covered?
This sounds obvious, but provider networks change. A doctor or specialist who was in-network last year may not be this year. A prescription that was covered at one tier may have moved to a different tier with a higher copay.
According to Kaiser Permanente’s health insurance questions guide, you should ask specifically which providers and networks are included in the available insurance options. If you have ongoing relationships with specific doctors, specialists, or a particular hospital system, verify that they are in-network under each plan you are considering before you enroll.
The prescription question matters separately. Ask your HR benefits team or the plan’s customer service line where your regular medications fall on the plan’s formulary, which is the list of covered drugs organized by cost tier. A medication that was in tier two last year may have moved to tier three, and that difference can add hundreds of dollars in annual prescription costs.
Should I Choose a High-Deductible Plan With an HSA?
High-deductible health plans often have lower monthly premiums, and when they’re paired with a Health Savings Account, they offer a tax advantage that can make them genuinely attractive for the right person. For 2026, the HSA contribution limits are $4,400 for individual coverage and $8,750 for family coverage, according to Lively’s HSA resource guide. Those contributions go in pre-tax, grow tax-free, and come out tax-free when used for qualified medical expenses. That’s a triple tax benefit that no other savings account offers.
The catch is that a high-deductible plan makes the most sense when you’re relatively healthy, don’t anticipate significant medical expenses, and can actually fund the HSA to take advantage of the tax benefit. If you have chronic conditions, planned procedures, or dependents with regular medical needs, the higher deductible may cost you more than the premium savings are worth.
According to ADP’s open enrollment guide, employees need to consider whether they’d rather pay less upfront in premiums or when they actually get care through a higher deductible. Running the math across a realistic scenario for your household is the only way to answer that question for your specific situation. Ask your HR team if they have a benefits calculator that lets you compare total annual costs across plan options.
What Is the Difference Between an FSA and an HSA?
These two accounts are frequently confused, and the confusion leads to people either not using them at all or making enrollment choices that don’t maximize their benefit.
A Health Savings Account is available only with a high-deductible health plan. The funds roll over from year to year, can be invested, and stay with you even if you change jobs. An FSA, or Flexible Spending Account, is available with most plan types but has a use-it-or-lose-it rule, meaning funds that aren’t spent by the end of the plan year are forfeited, with some employers allowing a small rollover or grace period.
You cannot contribute to both an HSA and a Healthcare FSA at the same time, according to Lively’s comparison guide. However, you can contribute to an HSA and a Dependent Care FSA simultaneously if your employer offers one, because the Dependent Care FSA covers childcare and eldercare expenses rather than medical ones.
The questions to ask: does your employer offer an HSA-eligible plan, does your employer contribute to the HSA on your behalf, and does the employer offer an FSA and if so what is the rollover policy?
What Life Changes Happened This Year?
Open enrollment is the right time to update your benefits based on what changed in your life over the past year. Marriage, divorce, a new child, a child aging off your plan, a change in your spouse’s coverage, a significant change in your health situation, all of these are qualifying life events that should trigger a review of your current elections rather than a default rollover.
According to the ADP open enrollment guide, employees can generally only change their health care coverage during the open enrollment period unless a qualifying life event occurs such as marriage, having a baby, or loss of other coverage. If you experienced any of those changes, open enrollment is your scheduled opportunity to update everything.
The questions to ask yourself: did my family situation change? Did my health situation change? Did my spouse’s employer coverage change? Is anyone aging off my plan or becoming newly eligible?
What Supplemental Benefits Am I Leaving on the Table?
Many employers offer supplemental benefits during open enrollment that most employees never look at closely. Disability insurance, life insurance, critical illness coverage, hospital indemnity insurance, accident insurance, legal assistance, commuter benefits, wellness programs, and employee assistance programs are all commonly offered and commonly ignored.
According to Ameriprise’s open enrollment guide, open enrollment is a good time to review employer-provided options including life insurance, long-term care insurance, and disability coverage. Employer-provided life insurance is often low-cost or free at a base level, with the option to purchase additional coverage at group rates that are typically better than what you’d pay individually.
The questions to ask: what supplemental benefits does my employer offer that I’m not currently enrolled in? What would they cost? Have my needs changed in a way that makes any of them newly worth considering?
How Does This Fit Into My Budget for Next Year?
This is the question that connects open enrollment to everything else in your financial life. Your health insurance premium affects your monthly take-home pay. Your FSA or HSA election reduces your taxable income but also reduces your liquid cash. Your deductible choice affects how much you need in your emergency fund to handle a bad health year.
Before you finalize any elections, it’s worth knowing what your total monthly benefits cost will be under each plan scenario and how that fits into your overall budget. If a higher premium plan significantly strains your monthly budget, the protection it offers may not be worth the cash flow impact. If a lower premium plan leaves you exposed to a deductible you couldn’t cover without going into debt, the premium savings are illusory.
A budgeting app with unlimited custom categories makes this kind of forward planning easier, because you can build out your anticipated monthly expenses under each plan scenario and see how the numbers fit. Lucky Friday is a free budgeting app available on iOS and web that lets you create any category structure you need, including a healthcare budget broken into premiums, expected copays, and HSA contributions. Core tools are free forever with no credit card required. Bank sync is available on the premium plan at $12.99 per month or $99.99 per year if you want automatic imports.
Once you have your benefits locked in for the year, tracking what you actually spend against your healthcare budget category is one of the ways a functioning budget earns its keep. Our post on why budgeting apps fail even when people are genuinely trying covers the habits that make the difference between a budget that works and one that gets abandoned. (https://luckyfriday.app/blog/why-budgeting-apps-fail-savings-rate-wake-up-call)
When Is the Deadline and What Happens If I Miss It?
This is a practical question that catches people off guard every year. Employer open enrollment periods typically run two to four weeks in the fall, and the deadline is real. If you miss it, your current elections generally roll over, which means any changes you wanted to make don’t happen, and any new benefits you wanted to add aren’t available until the following year unless you have a qualifying life event.
The deadline varies by employer. Many employer open enrollment periods run in October or November with new elections effective January 1. But some employers have different timing. Ask your HR team specifically when the open enrollment window closes and what the process is for submitting elections, whether that’s through an online portal, paper forms, or something else.
If you’re unsure where to start with building an emergency fund to handle your deductible in a bad health year, our guide on how to start an emergency fund when you’re already behind has a practical method that works at any income level. (https://luckyfriday.app/blog/how-to-start-an-emergency-fund-when-youre-already-behind-the-my-first-buffer-method)
Common Questions About Open Enrollment
What is the most important question to ask during open enrollment?
Ask what changed from last year. Plans change every year, networks change, premiums and deductibles shift. The biggest mistake people make during open enrollment is assuming this year’s plan is the same as last year’s and rolling over their elections without reviewing them. Starting with what changed gives you the information you need to evaluate whether your current selections still make sense.
What is the difference between a premium and a deductible?
Your premium is the amount you pay every month for health insurance coverage, whether or not you use any medical services. Your deductible is the amount you pay out of pocket for covered medical services before your insurance starts paying. A plan with a low premium often has a high deductible, and a plan with a high premium often has a lower deductible. Neither choice is automatically better. The right balance depends on how much medical care you expect to use during the year.
Should I choose an HSA-eligible plan during open enrollment?
An HSA-eligible high-deductible health plan makes the most sense if you’re relatively healthy, don’t anticipate significant medical expenses, and can fund the HSA to take advantage of the triple tax benefit. For 2026, you can contribute up to $4,400 as an individual or $8,750 for family coverage, all pre-tax. If you have chronic conditions, regular prescriptions, or planned procedures, run the full-year cost comparison before choosing the high-deductible option, as the deductible savings may cost more than the premium savings are worth.
What happens if I miss the open enrollment deadline?
If you miss your employer’s open enrollment deadline, your current elections generally roll over automatically. That means you can’t make changes to your plan selection, add dependents, or enroll in new supplemental coverage until the following year’s open enrollment, unless you experience a qualifying life event such as marriage, divorce, a new child, or loss of other coverage. Missing the deadline is particularly costly if you were planning to start contributing to an HSA or FSA, since those require active enrollment.
Can I change my benefits outside of open enrollment?
Generally no, with exceptions. You can make changes to your benefits outside of open enrollment if you experience a qualifying life event, which includes marriage, divorce, birth or adoption of a child, loss of other health coverage, a change in your spouse’s employment, or a move that affects your plan options. Outside of those events, open enrollment is your annual window for changes.
SOURCES:
Aflac WorkForces Report 2016 via PolicyGenius. 57% of employees spent less than 30 minutes on open enrollment. https://www.policygenius.com/health-insurance/news/blast-open-enrollment-smart-way-checklist/
Kaiser Family Foundation. 2025 Employer Health Benefits Survey. Average family premiums reached $26,993 in 2025, a 6% increase outpacing wage growth. Via HR Executive. https://hrexecutive.com/employees-arent-confused-about-their-benefits-theyre-anxious
Lively. 2026 Maximum HSA Contribution Limits. $4,400 individual, $8,750 family for 2026. HSA vs FSA comparison. https://livelyme.com/blog/employee-benefits-questions-to-ask-during-open-enrollment
Kaiser Permanente. 10 Health Insurance Questions to Ask Your New Employer. Provider networks, premiums, deductibles, HSA and FSA. https://healthy.kaiserpermanente.org/learn/hc.health-insurance-questions-employer
Included Health. Clear the Confusion: Top 5 Employee Questions for Open Enrollment. Premium vs deductible tradeoffs, HDHP and HSA pairing, benefits jargon explained. https://includedhealth.com/resources/clear-the-confusion-top-5-employee-questions-for-open-enrollment/
ADP. HR’s Guide to Open Enrollment. Qualifying life events, deductible vs premium explanation, HSA with high-deductible plans. https://www.adp.com/spark/articles/2018/07/hrs-guide-to-open-enrollment.aspx
Ameriprise Financial. Your Open Enrollment Checklist: 7 Questions to Ask. Life insurance, disability coverage, supplemental benefits review. https://www.ameriprise.com/financial-goals-priorities/insurance-health/health-insurance-open-enrollment
OneDigital. Open Enrollment FAQs for Small Business Owners. Common employee questions, FSA vs HSA, open enrollment timing. https://www.onedigital.com/blog/open-enrollment-faqs-for-small-business-owners-how-to-make-it-easier-on-you-and-your-team/