Open Enrollment Is Here: The 15-Minute Benefits Check That's Worth More Than Your Raise

🤖 This article was produced with AI assistance and reviewed by our editorial team.

The fastest way to get more out of open enrollment is to do four things before your deadline: price your health plans for a bad year, not just a normal one; fund an HSA if you're eligible; claim every dollar your employer puts on the table; and skim the perks list you've never opened. For a typical single worker, that can be worth more than a 3% raise, which on a $70,000 salary is $2,100 before taxes.

Most people skip it. Open enrollment is the one window each year when you can change most benefits without a qualifying life event like a marriage or a new baby. Miss it, and you live with this year's choices until next fall.

Why this year's open enrollment is different

Health coverage is getting more expensive, fast. Employers expect benefit costs per employee to rise 8.2% on average in 2027, even after cost-cutting changes, according to Mercer's survey released in September 2026. Without those changes the increase would have been 11%, the biggest jump since 2003.

A lot of that cost is landing on workers. In the same survey, about two-thirds of large employers said they expect to raise the share of premiums employees pay. So the plan that was the right call last year may not be this year. Your premiums, deductibles and even the plan list itself could have changed, and auto-renewal won't tell you.

Step 1: Pick your health plan with the "bad year" math

Most people compare plans by the paycheck deduction. That's half the picture. The full cost of a plan is your premiums plus whatever you'd pay out of pocket, and the out-of-pocket maximum (the most you can pay for covered care in a year before insurance pays 100%) tells you the worst case.

Here's one worked example with hypothetical numbers. Your plan's numbers will be different, but the math is the same. Jordan is 29, single, and choosing between two plans:

That won't always be the result. A PPO can win if your employer subsidizes it heavily, if you have predictable ongoing costs that its copays cover cheaply, or if you couldn't come up with a $2,500 deductible in cash on short notice. That last one is real: an HDHP asks you to front more money before insurance kicks in, which is one more reason to keep a cash runway you can reach in a hurry. If you don't have that cushion yet, our guide to calculating your emergency fund number is the place to start.

Run your own version: for each plan, add annual premiums to the out-of-pocket max, then subtract any employer HSA money. Do it for a quiet year too. If one plan wins both, the decision is made.

Step 2: Use the HSA, the only triple tax break in the tax code

If you pick an HSA-eligible HDHP, you can open a Health Savings Account. It's the rare account that's tax-free three times: contributions go in before tax, the money grows tax-free, and withdrawals for qualified medical expenses come out tax-free. No other account gets all three.

For 2027, the IRS set the HSA limits at $4,500 for self-only coverage and $9,000 for family coverage, plus a $1,000 catch-up if you're 55 or older (Rev. Proc. 2026-24, released June 2026). Your employer's deposit counts toward those limits. Contributing through payroll is usually better than depositing on your own, because payroll contributions also skip Social Security and Medicare taxes. If Jordan adds $1,500 through payroll in the 22% federal bracket, that saves roughly $445 in federal income and payroll taxes. One catch for readers in California and New Jersey: those two states still tax HSA contributions and growth at the state level.

The move that makes an HSA powerful is not spending it. Pay small medical bills from your checking account, keep the receipts, and invest the HSA balance. The IRS sets no deadline for reimbursing yourself for a qualified expense incurred after the HSA was opened, so a receipt from 2027 can be reimbursed tax-free years later. In the meantime the money compounds. We walk through the investing side in our complete guide to using an HSA as a retirement account, and if your marketplace plan just became HSA-eligible, see what changed for bronze plans in 2026.

Step 3: Claim the free money you're skipping

This is where the "worth more than your raise" part shows up. Check three things:

• Employer HSA deposits. Some employers fund your HSA automatically, but some only do it if you enroll in a wellness program or contribute yourself. Read the fine print, because unclaimed seed money is a pure loss.
• Your full 401(k) match. You can change 401(k) contributions any time of year, but open enrollment is a natural moment to confirm you're contributing at least enough to get the full match. Leaving part of a match on the table is turning down part of your salary.
• Flexible spending accounts (FSAs). A health FSA lets you pay for medical costs pre-tax ($3,400 limit for 2026; the 2027 limit hadn't been announced as of October 2026). A dependent care FSA covers childcare or daycare pre-tax, and its household limit rose to $7,500 starting in 2026. The catch is "use it or lose it": money you don't spend by the deadline is forfeited, unless your plan offers a small carryover or a grace period. Elect only what you're confident you'll spend.

One rule to know: you generally can't have a regular health FSA and contribute to an HSA in the same year. If you're switching to an HDHP, skip the health FSA (or ask whether your employer offers a "limited-purpose" FSA for dental and vision, which is allowed alongside an HSA).

Step 4: The perks nobody reads

Benefits portals bury the good stuff at the bottom. Five minutes of scrolling often turns up:

• Commuter benefits that let you pay for transit or work parking pre-tax.
• Free basic life insurance, often one times your salary. Check whether your beneficiary is up to date.
• Disability insurance, which replaces part of your income if you can't work. If it's offered cheaply, it's one of the most underrated benefits for young workers, since your future paycheck is your biggest asset.
• An employee assistance program (EAP) with free short-term counseling, financial coaching or legal consultations.
• Discounted pet insurance. Group rates can beat buying on your own, but run the numbers first with our pet insurance vs. emergency fund break-even math.

Your 15-minute open enrollment checklist

1. Find your deadline and put it on your calendar with a reminder two days before.
2. Open the plan comparison and note each plan's premiums, deductible and out-of-pocket max.
3. Do the bad-year and quiet-year math for each plan.
4. If you choose an HDHP, set your HSA payroll contribution and claim any employer deposit.
5. Confirm your 401(k) contribution captures the full match.
6. Elect an FSA only for spending you're sure of.
7. Scroll the perks list, update beneficiaries, and save your confirmation page.

Plan details and limits change every year, so treat the figures here as accurate as of October 2026 and confirm them against your own benefits guide.

Frequently asked questions

Can I change my health plan in the middle of the year?

Usually only after a qualifying life event, such as marriage, a new child, or losing other coverage, and you typically have 30 days to act. Otherwise, the choice you make during open enrollment holds for the full plan year.

Is a high-deductible plan a bad idea if I'm healthy but nervous about costs?

Not necessarily. Compare each plan's worst case: premiums plus the out-of-pocket max, minus any employer HSA deposit. If the HDHP still wins and you have enough cash saved to cover the deductible, the main risk is cash flow, not total cost.

What happens to my HSA if I leave my job?

It stays yours. Unlike an FSA, an HSA is owned by you, not your employer, so the balance and any investments go with you. You can keep using it for qualified medical expenses even if you're no longer on an HDHP, though you can only contribute while you have HSA-eligible coverage.