The Roth series · By Rich LoPresti, CFP®
One of you will file alone. The tax code will notice.
It's called the widow's penalty, and it's one of the least understood reasons to plan your taxes while you're both here.
The short answer. When a married couple becomes a household of one, the surviving spouse usually starts filing as a single person, generally from the year after the death, unless another filing status applies. Most of the tax brackets are roughly half as wide, the standard deduction is cut in half, and the income thresholds for Medicare surcharges drop too. But the income often barely falls: the smaller Social Security check goes away, and maybe part of a pension, while the IRA and its required withdrawals stay exactly where they were. The result is a higher tax rate on nearly the same income, for the rest of the survivor's life. Money that's in a Roth doesn't show up on that tax return at all, which is why building one while you're both alive is one of the most caring things a couple can do for each other.
Same house, same bills, half the brackets.
Most people don't think about this until they're in it. Here's what the 2026 brackets look like side by side:
| Rate | Married filing jointly | Single, the survivor |
|---|---|---|
| 10% | Up to $24,800 | Up to $12,400 |
| 12% | Up to $100,800 | Up to $50,400 |
| 22% | Up to $211,400 | Up to $105,700 |
| 24% | Up to $403,550 | Up to $201,775 |
| Standard deduction | $32,200 | $16,100 |
2026 federal figures on taxable income, as published by the IRS. Additional deductions for those 65 and older are not shown.
What that does to the same income.
Take $100,000 of taxable income, and nothing else changes except the filing status.
Tax-law arithmetic · $100,000 of taxable income · 2026 federal brackets
Same income, different return.
Federal income tax on $100,000 of taxable income under each filing status, calculated directly from the 2026 brackets. This is how the tax code works, not a projection of anyone's taxes or a measure of any strategy.
That's about 45% more federal tax on exactly the same taxable income. And it's usually worse in real life, because the smaller standard deduction means more of the survivor's income is taxable to begin with.
Why the income doesn't fall the way you'd think.
When I walk couples through this, the reaction is usually "but there's only one of us now, so we'll need less." Some expenses do go down. Most don't. The house, the property tax, the insurance and the car are all still there.
And the income that's left is the income you can't turn off:
- Social Security: the survivor generally keeps the larger of the two checks, and the smaller one stops.
- A pension: it continues only if a survivor option was chosen at retirement, and that choice is usually permanent.
- Required withdrawals: they're based on the account balance, not on how many people live in the house. The IRS doesn't care that the survivor is 85 and alone. The freight train →
In Connecticut there's one more step down. The state's exemptions for Social Security and for pension and IRA income each work a little differently, but both start shrinking at $100,000 of federal AGI for a married couple, and at $75,000 for a single filer.
What you can do about it while you're both here.
Much of this is hard to fix after the fact. All of it can be planned for in advance.
- Build the Roth at joint rates. Converting while you're both alive means paying tax in the wider married brackets. And Roth withdrawals don't appear on the survivor's tax return, so they don't push the survivor into a higher bracket or a Medicare surcharge.
- Treat Social Security as survivor insurance. The larger benefit becomes the survivor's benefit. Waiting to claim it, where that makes sense, raises the check the survivor keeps for life.
- Choose pension options with the survivor in mind. The single-life option pays more today, but stops at the first death. Look at every option in dollars before signing.
- Keep the beneficiary forms current. Every retirement account passes by its own form, not your will.
And then it happens again, to your children.
When your children inherit a traditional IRA, most of them have to empty it within ten years, and every pre-tax dollar is taxed as ordinary income on top of their own salaries, often in their peak earning years. An inherited Roth generally has the same ten-year clock, but the money comes out tax-free. So the same Roth that protects the survivor also protects the next generation. It isn't that the same dollar gets taxed twice. It's that the bill can come due later, on a bigger account, in someone else's higher bracket. I'd rather you pay it once, at a rate you choose.
Bring it back to your plan
Four questions worth asking
- If one of us passed away, what income would the survivor have, and how would it be taxed?
- Whose Social Security benefit is larger, and when should that one be claimed?
- If either of us has a pension, what does the survivor receive under each option?
- How much of our savings would the survivor be forced to withdraw each year, and at what rate?
What this article does not show.
Worth being explicit, because an article like this can imply more than it should.
- It is not a projection. The $100,000 example shows how the tax code treats the same income under two filing statuses. It does not estimate anyone's taxes or any tax saved.
- Every household is different. Some survivors spend much less, have little in pre-tax accounts, or qualify for other filing statuses for a time. Rules for surviving spouses with dependent children differ.
- Conversions cost real money. A Roth conversion is taxable income in the year it happens, and paying that tax today is a real cost.
- Tax law changes. Brackets, deductions, Medicare thresholds, state rules and inherited-account rules are shown as they stand in 2026.
Part of a series on the Roth. Start with The Roth isn't a tax break. It's a steering wheel.
Try it on your own dates
Is this worth a look for you?
Two minutes, eight questions, nothing saved. Or map the years between your last paycheck and your first required withdrawal.
Take the two-minute check → Map your conversion window →The timing
Why the years right after the paychecks stop are often the cheapest time to convert.
Read the article →What to convert
Why one blended fund makes it hard to put the right assets in the Roth.
One fund got you here →Plan for both of you, and for whoever is left.
An hour is enough to see what the survivor's tax return would look like, and what you can still change while you're both here.
Talk with Rich →Sources: IRS Publication 590-A and Publication 590-B (IRAs and Roth IRAs); IRS 2026 inflation adjustments for tax brackets and standard deductions; Social Security Administration, Medicare Premiums: Rules for Higher-Income Beneficiaries; Connecticut Department of Revenue Services.
Educational content written by Rich LoPresti, CFP®, drawing on recurring planning conversations. It is not a client case study, testimonial or individualized recommendation. Federal brackets and standard deductions are 2026 IRS figures; a surviving spouse may generally file jointly for the year of death, and qualifying surviving spouse status is available only in limited circumstances. Social Security survivor benefits depend on each spouse's record and claiming age. Inherited-account rules vary by beneficiary type. Connecticut thresholds reflect current Connecticut law. Consult a qualified tax advisor. Retirement Approaching provides retirement-planning education. Advisory services are offered through Milestone Asset Management Group, LLC, an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. No investment result or tax savings is guaranteed.