Photo by Priscilla Du Preez 🇨🇦 on Unsplash
Confused about your workplace benefits options this enrollment season? Your answers to the following eight questions could help you pick the best benefits, some of which also offer tax savings, for you and your family.
If you work for a company that provides benefits, then you’ve probably been sorting through material about those benefits, notably your medical coverage.
Or not. If you’re happy with your current benefits, you’re probably tempted to just let it ride into next year.
I get it. It’s easy. But you could cost yourself, both in out-of-pocket expenses and tax savings.
So, before you make a final decision, consider asking yourself the following eight questions.
1. Have I fully explored what’s being offered?
This seems obvious, but we all know how hectic life can get. If you’re happy with your current coverage, and it’s being continued into 2027, you might be tempted to just let it slide into the next year.
But it couldn’t hurt to look at what else is available. It doesn’t take that long. And you might find another option fits your situation better.
For most employees, company-provided medical coverage is their most important (and expensive) benefit. While most workers are just glad to have health insurance, the employee portion of the premium still is often substantial. So, look at what’s being offered this year and compare. You might get similar (or better) coverage for a smaller premium.
This review is especially important if you’ve experienced a life-changing event and didn’t use it when it happened to make changes to your benefits.
2. Will a high-deductible health care plan work for you?
OK, you’ve examined other medical insurance options and are interested in a high deductible health plan (HDHP). These medical insurance plans are appealing because, as its name spells out, it has lower per-paycheck premiums in exchange for a higher deductible applied to medical costs. That’s a workable trade-off for many young and healthy employees.
The dollars associated with these plans and spending accounts are adjusted annually for inflation. For the 2027 tax year, the maximum deductible for a single policy holder is $1,750; it’s a $3,500 deductible for family coverage.
Maximum out-of-pocket expenditures for a single HDHP enrollee is $8,700 and $17,400 for family expenditures. Out-of-pocket expenses include deductibles, co-payments and other medical costs, but not the premiums you pay for the plan itself.
If a high deductible is for you, you’ll want to open and fund as fully as possible an associated health savings account, or HSA. This money helps you offset your higher deductibles. More on this in.
If you do opt for an HDHP plan this benefits enrollment season, you’ll also want to check into establishing an associated health savings account, or HSA. You put money into the HSA, where it grows tax-free. Then you can make tax-free withdrawals for qualified medical expenses.
The HSA contribution maximum for 2027 is $4,500 if you’re a single taxpayer or $9,000 if the coverage is for families with high deductible health plans. There’s also a $1,000 add-on for 55 or older HDHP plan owners.
Even better, the money that you put into an HSA is totally yours, not your employer’s even if it’s offered via your workplace, meaning it rolls over from year-to-year and if you change jobs, it still belongs to you.
3. Would you benefit from a health care flexible spending account (FSA)?
There’s a similar tax-favored medical payment account for workers who opt for traditional health coverage. Flexible spending accounts, or FSAs, allow you to put preset amount from your paycheck into the FSA each payday before taxes are figured.
While you will lose some of your paycheck to the money going into the FSA, your taxes will be reduced a bit, so the bottom-line pay period change tends to be nominal. The tax benefits really come in handy when you get to use those pre-tax dollars to cover eligible medical expenses, including copays and deductibles.
The Internal Revenue Service should soon release 2027 inflation adjustment numbers. Until then, you can use the 2026 amounts as a base, with the expectation it will be bumped up a bit. That’s a maximum FSA contribution of $3,400.
Regardless of the eventual 2027 FSA limit, deciding how much to put into an FSA requires some tax and medical prognostication. You don’t want to underestimate the amount, but neither do you want to over-contribute.
Why the need for the benefits math? Even with some allowances to let you use up your FSA funds, such as rollovers to the next benefits year or grace periods giving you until mid-March to spend the money, the accounts are still use-or-lose arrangements. Any unspent amounts in an FSA go back to your boss.
4. Could a child care spending account come in handy?
More companies are trying to be family-friendly, especially since younger workers have expressed more interest in achieving a better work-life balance.
One long-time workplace benefit that can help is a dependent care flexible spending account (DCFSA). It’s essentially a benefits-plan cousin to a medical FSA. You put pre-tax paycheck contributions into the child care FSA and use them to cover some of the care costs.
With this added financial assistance from the boss, parents might have a bit more leeway in finding a caregiver that meets their family’s needs.
The amount you can contribute each year to a DCFSA is not affected by inflation. But the One Big Beautiful Bill Act of 2025 did increase, for the first time since the 1980s, how much you can put into this account.
Starting with the 2026 tax year, the limit went from $5,000 to $7,500 for single taxpayers and married couples filing jointly. Married couples who file separately can put up to $3,750 (an increase from prior law’s $2,500) into a DCFSA.
The qualifying costs that can be paid from a dependent care account include preschool care, before or after school programs, other private child care costs, and even summer day camp.
5. Does your workplace offer a Trump Account employer contribution?
Parents probably also have heard about Trump Accounts, a tax-advantaged savings option for U.S. citizens age 17 and younger. It essentially is a starter IRA, but with different contribution limits, investment rules, distribution guidelines, and other requirements.
Moms and dads, grandparents and other relatives, guardians, and even family friends can contribute a combined total of up to $5,000 a year to benefit the minor child for whom the Trump Account was established.
In some instances, Uncle Sam also will make a one-time $1,000 contribution. This special amount is for U.S. children born between in 2025 through 2028, and does not count toward the $5,000 contribution cap.
Employers also can get in on the Trumps Savings act. Companies can contribute up to $2,500 per year toward an employee’s or dependent’s Trump Account. More than 100 companies have opted so far to make such contributions. Participation tracking, however, could lag, so check directly with your benefits advisor about Trump Account contributions.
The businesses generally get a tax deduction for the contributions. As for the workers, the Trump Account amounts are not counted as taxable income.
Note, however, that the employer contribution does count toward the total $5,000 maximum annual cap. So, if your workplace maxes out its contribution to the special childhood savings plan, others can only contribute a combined $2,500 to your child’s Trump Account.
6. Will your company help you repay your student loan?
College costs and the debt that students and their families go into to pay for higher education continues to be a challenge. Things have become more complicated in many cases, during the second Trump administration. The OBBBA and other recent legislation has changed, effective July 1, student loan borrowing limits and repayment plans.
Some businesses, however, offer their workers help in paying student loans. These programs have been available for many years, with workers using them to pay for books, equipment, supplies, fees, tuition, and other education expenses. Since March 27, 2020, tax-free educational assistance benefits also include principal or interest payments on certain qualified education loans incurred by the employee for the education of the employee.
The amount that can be provided tax-free to workers is $5,250 per employee per year. This limit will be adjusted annually for increases in the cost-of-living (aka inflation) beginning in 2027.
If you’re paying off college costs, find out whether your employer’s educational assistance program includes the loan payment option. If it does, don’t miss out on this chance to get payment help from the boss.
7. Does your spouse also get workplace benefits?
Marriage is a partnership and that definitely applies during workplace benefits enrollment time. If you and your spouse both have jobs that offer benefits, don’t make any decisions about what job perks are offered in either place before checking with each other. You need to understand what each package offers, how benefits from each workplace are coordinated, and know of any potential marital limits.
This is particularly true if you have children and are considering a dependent care account discussed in question #4.
Even though each parent’s workplace allows them to contribute up to $5,000 in a child care account, the tax code says that working parents’ combined contributions to separate childcare spending accounts cannot exceed $5,000. Don’t get stuck over contributing to this benefit.
As for healthcare, assess the options each spouse’s workplace offers. Will you get lower premiums if you sign up with your lower-earning spouse’s healthcare plan? Or will those premium savings be lost if you must pay higher deductibles or copays? Should each spouse sign up separately for his or her own workplace plans? If so, which one should cover the kids? If you go with one spouse’s medical coverage for the full family, is that spouse’s job and therefore insurance the more secure one?
OK, that’s a lot more than the eight questions (the last one starts after this paragraph) touted at the beginning of this post. And yes, sorting through dual workplace open enrollment options is one of those relatively worse times you agreed to in your vows.
But it’s an exercise that could pay off financially (and tax-wise), improve your combined workplace benefits, and strengthen your relationship.
8. Are you saving enough for your retirement?
How much we’ll enjoy our post-work years depends in large part on whether we’ll have enough money for the kind of retirement we want. A workplace 401(k) plan can help. If you work for a government agency or nonprofit, you’ll likely be offered a 403(b) plan. Those names come from the Internal Revenue Code section under which they are governed.
Workplace retirement contribution plans generally aren’t an official part of the annual open enrollment time frame because you usually can change your 401(k) choices on a payroll period basis. But since you’re looking at all your other employer-sponsored perks now, it’s also a good time to also evaluate your retirement plan options.
Regardless of which tax code section number is assigned to your workplace retirement plan, these programs allow you to contribute to your nest egg via a tax-favored workplace plan. Your employer also can contribute a percentage to your account.
The first step is opening a workplace retirement account. The next one is putting in enough of your own money to get your company’s match.
Under a traditional 401(k) plan used by most private sector firms, your money goes in pre-tax and grows tax-deferred. When you eventually take distributions, those amounts are taxed at your ordinary income tax rate.
Some businesses, however, also offer Roth 401(k)s, which are funded with your already taxed contributions. The benefit here, as with a Roth IRA, is that qualified withdrawals are tax-free.
The contribution limit for the 2026 tax year for employees who participate in 401(k) and similar plans is $24,500. There’s also a plan catch-up contribution limit of $8,000 this year for employees aged 50 or older and who participate in these plans. If your personal budget allows, use these next couple of months to boost your workplace retirement savings plan.
And if you can afford to put in the maximum annual contribution amount, can we talk offline about me visiting the lakefront villa you’re obviously planning on moving into when you retire?! 😉
Again, evaluation before keeping or changing benefits is key.
As noted at the top of this post, it’s tempting during open enrollment to simply sign up for the benefits you already have in place.
But it’s to your benefit, pun intended, to take the time to actually look at what’s being offered for the coming year. Companies do change their benefits plans. And it’s a pretty safe bet that at least your portion of healthcare premiums for next year are higher.
Your life also might have changed. Or you’re making plans for such eventualities. While you can make some benefits changes as major life events occur, thinking about them in advance can’t hurt.
And by selecting the most beneficial workplace benefits now for you and your family, you’ll ensure those company-provided perks really pay off regardless of what the future holds.
