The benefits email shows up sometime in October. You skim it, you see that your current elections will roll forward automatically if you do nothing, and you do nothing. Deadline passes. Done.
The impulse makes sense. Benefits guides are badly written, the deadline always lands during a busy stretch, and the decision feels low-stakes because the dollar amounts are small on any given paycheck.
They’re not small over twelve months, though. And a few things changed for 2027 that make this year worth a second look.
Start with the HSA numbers
The IRS put out the 2027 figures back in May. If you’re on an HSA-qualified high-deductible plan you can put in $4,500 with self-only coverage, or $9,000 with family coverage. Those are up from $4,400 and $8,750. Anyone 55 or older gets another $1,000 on top, and that catch-up number is written into the statute, so it doesn’t budge with inflation the way the rest do.
For the plan itself to qualify in 2027 it needs a deductible of at least $1,750 self-only or $3,500 family, with out-of-pocket capped at $8,700 and $17,400.
Now, the part that costs people money. Your payroll deduction usually carries forward at whatever you set last year. The limit went up; your contribution didn’t. You end the year a couple hundred dollars short of the max and there’s no way to go back and fix it. Just reset the number.
Two eligibility changes that might apply to you
If you’ve been told in the past that you couldn’t contribute to an HSA, that answer may be stale.
Bronze and catastrophic plans bought through the ACA marketplace became HSA-compatible on January 1 of this year. That’s relevant if you’re self-employed, retired before 65 and bridging to Medicare, or otherwise buying your own coverage.
The other one is direct primary care. Those monthly-fee arrangements used to wreck your HSA eligibility entirely, because they counted as disqualifying secondary coverage. Under the OBBBA they don’t anymore, so long as the fees stay at or under $150 a month for one person or $300 for an arrangement covering more than one.
Read that threshold carefully, because it isn’t prorated. A $160 monthly membership doesn’t cost you a slice of your eligibility. It costs you all of it.
One more on this: telehealth before you’ve met your deductible is now permanently fine and won’t affect your HSA either.
A 401(k) wrinkle that’s catching people this year
Not strictly an open enrollment item, but it hits the same season and it’s come up in a lot of conversations this year.
As of 2026, if your prior-year wages from your employer were above roughly $145,000, your catch-up contributions have to go into Roth. The pre-tax deduction on that portion is gone.
Two consequences. If your plan doesn’t offer a Roth option, you may not be able to make catch-up contributions at all right now, not until the plan gets amended. And if you’d been leaning on that deduction to hold your taxable income down, that lever is shorter than it was. Worth checking your withholding.
The friendlier side of the same rules: if you’re between 60 and 63, there’s a larger “super catch-up” available to you. It’s a four-year window and plenty of people go through it without ever using it.
Worth thinking through
Anything change in your life this year? New baby, spouse switched jobs, kid aged off the plan, a diagnosis, a divorce. Any one of those can turn last year’s right answer into this year’s wrong one, and the plan doesn’t know about it.
On the HDHP question — the premium savings get all the attention, but the HSA is the real reason to consider one. Money goes in pre-tax, grows untaxed, comes out untaxed for medical costs. If you can cover this year’s doctor bills from cash flow and leave the account alone to compound, it’s arguably the best-treated account in the code. If you’d be draining it every December, that math looks very different and the cheaper premium may not be worth the exposure.
Related, and this one surprises people: a lot of HSA money never gets invested. It just sits in the cash sweep earning nearly nothing for a decade. If you’re treating the account as long-term savings, go check what it’s invested in.
Then there’s disability. Group LTD through your employer is a fine starting point and it’s almost never the whole answer. The benefit is typically capped at a percentage of income, it’s taxable to you if your employer paid the premium, and it goes away when you leave. What matters more than any of that is how the policy defines “disabled.” For physicians and other specialists especially, an own-occupation definition on a portable individual policy is frequently the difference between a claim getting paid and a claim getting denied. If you’ve never read that language in your own coverage, this is a good month to.
Last thing, and it’s the easiest: make sure you’re capturing whatever your employer is handing out. Match, HSA seed money, wellness credits. Cheapest dollars you’ll ever get.
The Bottom Line
Put thirty minutes on the calendar before the deadline. Pull up last year’s elections next to this year’s guide and compare them line by line instead of going from memory, because memory is usually wrong about this stuff.
And if your situation has real moving parts this year — a working spouse with a competing plan, income that swings, equity comp, a coverage question you keep going back and forth on — have that conversation while you can still act on it. Open enrollment is one of the few financial deadlines with no extension and no amended return.
Securities offered through Registered Representatives of Cambridge Investment Research, Inc., a Broker/Dealer, Member FINRA/SIPC. Advisory services offered through Cambridge, a Registered Investment Advisor. Sound Foundation Wealth Advisors and Cambridge Investment Research, Inc. are not affiliated.
