Open Enrollment Is Here — Here's the Free Money You're Probably Leaving on the Table

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Open enrollment season is creeping up on most workplaces right now, and if you're like a lot of people in their 20s and early 30s, you probably treat it the same way you treat a phone software update: click through the defaults as fast as possible and get back to your day. That's a mistake, and it's an expensive one, because open enrollment is one of the few windows all year where actual free money is sitting on the table waiting for you to claim it.

Let's talk about the two accounts most people mix up — HSA and FSA — and how to not leave money behind this year.

A Health Savings Account (HSA) and a Flexible Spending Account (FSA) both let you set aside pre-tax money for healthcare costs, and that's basically where the similarities end.

An HSA is yours. It rolls over every year, forever, with no expiration. It's only available if you're enrolled in a qualifying high-deductible health plan (HDHP), but the eligibility rules got noticeably friendlier — as of 2026, Bronze and Catastrophic marketplace plans automatically qualify, whether or not they technically meet the older deductible rules. Money goes in pre-tax, grows tax-free, and comes out tax-free for qualified medical expenses. That's a triple tax advantage no other account gives you, including your 401(k).

An FSA is your employer's, sort of. You elect an amount during open enrollment, it comes out of your paycheck pre-tax all year, and — this is the part that trips people up — in most plans, whatever you don't spend by the deadline is gone. Some employers allow a small carryover into the next year, but it's usually capped in the hundreds of dollars, not the full balance.

The IRS has already locked in 2027 HSA limits: $4,500 for individual coverage and $9,000 for family coverage, both up from 2026's $4,400 and $8,750. For 2026 health FSAs, the limit is $3,400, with employers allowed to permit a carryover of up to $680 into the following year. One important rule: you generally can't fully fund a standard FSA and an HSA in the same year — if you have an HSA, you're limited to a "limited-purpose" FSA that only covers things like dental and vision.

Here's the piece that actually matters most for your wallet: check whether your employer contributes to your HSA. A lot of companies kick in $500–$1,500 a year automatically or as a match, on top of whatever you contribute yourself. That employer contribution counts toward your annual limit, but it's still money you didn't have to earn twice — functionally identical to a 401(k) match, and just as easy to accidentally skip if you opt out of the HDHP without checking.

1. Actually check if you're HSA-eligible before defaulting into the PPO. A lot of people default into the plan they had last year, or the one HR pre-selects, without comparing the premium difference against what an employer HSA contribution would be worth.

2. If you're HSA-eligible, find out your employer's contribution before you decide your own. If they're putting in $750 a year, that changes the math on which plan actually costs less once you account for premiums and deductibles.

3. Set your FSA election conservatively, not optimistically. Look at what you actually spent on eligible expenses last year — copays, prescriptions, contacts — and elect close to that number. Use-it-or-lose-it means overestimating is the more expensive mistake, not underestimating.

4. If you have an HSA, don't rush to spend it. Unlike an FSA, there's no deadline. Many providers let you invest your HSA balance once it hits a minimum threshold, turning it into a stealth long-term account for future medical costs, including in retirement. Paying small medical bills out of pocket now and letting the HSA balance grow is a legitimate strategy if your cash flow allows it.

Open enrollment isn't just paperwork — it's one of maybe two or three moments a year where a five-minute decision can be worth real, recurring money. Between employer HSA contributions and getting your FSA election right, this is the same category of "free money you're probably not claiming" that we usually talk about with bank bonuses. Don't let it be the one you skip because the deadline snuck up on you.