Open Enrollment: What to Review Before You Finalize Your Benefits
Open enrollment isn't just about picking a health plan — it's your once-a-year chance to review benefit elections that often go untouched. Here's what's actually worth a second look.
Open enrollment season arrives every fall whether you're ready for it or not — a short window to make a stack of benefit elections that, once submitted, often go untouched until next year. It's worth treating as more than a health plan decision.
Here's a broader list of what's actually worth a second look before you finalize your elections.
Start With Your Health Plan Options
If your employer offers more than one health plan, compare total expected cost, not just the premium — a lower-premium plan with a much higher deductible can cost more in a year with meaningful medical expenses. If you're eligible for a health savings account, that's worth particular attention: to qualify as HSA-eligible for 2026, a plan needs a deductible of at least $1,700 for self-only coverage or $3,400 for family, and it can't cap out-of-pocket costs above $8,500 or $17,000. These thresholds move every year, so a plan that qualified last year isn't guaranteed to qualify again.
If You Stay HSA-Eligible, Check the Contribution Limits
The 2026 HSA contribution limits are $4,400 for self-only coverage and $8,750 for family, plus an additional $1,000 if you're 55 or older. These limits apply regardless of who contributes — you, your employer, or both — so check your total year-to-date contributions across all sources before assuming you have room left. And don't confuse an HSA with a general-purpose FSA: enrolling in one while you're also HSA-eligible can disqualify you from contributing to the HSA at all, even if the FSA belongs to a spouse rather than you.
Review Your Life Insurance and Disability Elections
Group life and disability coverage through work is often set once, in a first year of employment, and never revisited. If your income, mortgage, or family situation has changed since then, it's worth checking whether your current elections (which are often a multiple of salary) still make sense, and whether supplemental coverage is worth adding while it's available without medical underwriting.
Dependent Care and Other FSAs
A dependent care FSA lets you set aside pre-tax dollars for child care or elder care expenses, separate from a health FSA and unaffected by HSA eligibility rules. A limited-purpose FSA, which covers only dental and vision expenses, can also run alongside an HSA without disqualifying it — worth asking about if your employer offers one.
New Elections Need New Beneficiary Designations
Any new life insurance policy or retirement account election opens with a beneficiary designation of its own — and it's easy to leave the default in place without noticing. This is a natural moment to confirm the names on file match your actual wishes, particularly if you've had a marriage, divorce, or new child since you last enrolled.
The Windward Approach
A benefits enrollment window touches more of your financial plan than it usually gets credit for — your health coverage, your tax-advantaged savings options, your insurance protection, and your beneficiary designations all get touched at once. We're happy to look at your specific options if it would help before you finalize your elections.
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