Most people assume the tax code punishes the working class and rewards the wealthy. Rosalind Underwood believed that for most of her adult life — and she wasn’t entirely wrong. But the part she missed was this: there are real, meaningful credits and deductions written specifically for people like her, and they go unclaimed every single year not because they don’t exist, but because no one ever sat down to explain them.
I met Rosalind on a cold Thursday morning in late January 2026, at a Volunteer Income Tax Assistance (VITA) clinic hosted by a community center in Kansas City, Missouri. She was sitting in a plastic chair with a manila folder on her lap, wearing her school ID badge — she’d come straight from a half-day at the high school where she’s taught math for 31 years. I was there reporting on how middle-income earners navigate free tax services, and something about her calm, methodical energy made me want to hear her story.
When I sat down with Rosalind Underwood after her appointment, the first thing she said was that she almost didn’t come. “I’ve always done my own taxes,” she told me, smoothing the folder on her knee. “I teach math. I figured I had it handled.”
The Financial Picture She Walked In With
At 62, Rosalind earns approximately $68,400 a year as a public school teacher — a salary that sounds stable until you stack it against Kansas City’s rising cost of living, a mortgage, and the $31,200 still remaining on the student loans she took out for her master’s degree in mathematics education back in 2004. Her husband, Dennis, works in facilities management and brings in roughly $49,000 annually, putting their household income at just over $117,000.
That income level is often called “upper-middle class,” but Rosalind bristled slightly when I used that phrase. “Upper-middle class doesn’t account for what you owe,” she said. “We’re comfortable on paper. But we’ve got my loans, we’ve got a 17-year-old who starts college in the fall, and my school supply budget comes out of my own pocket every single year.”
For the 2025 tax year, Rosalind had prepared her return the same way she had for the past decade — using a popular retail software program, answering questions quickly, and submitting before the end of January. She expected a modest refund of around $340. When the VITA volunteer pulled up her return and began asking questions, the number started to shift.
The Deductions She Had Been Walking Past for Years
The first thing the VITA volunteer flagged was the educator expense deduction. Under current IRS guidelines, eligible K-12 teachers can deduct up to $300 in out-of-pocket classroom expenses — and that limit rose from $250 in 2022. Rosalind had been claiming $0 for the past several years, not because she didn’t spend the money, but because she assumed her receipts were too scattered to bother tracking.
“I buy graph paper, dry-erase markers, pencils for kids who show up without any,” she explained to me. “Last year I bought a used graphing calculator set off a teacher who was retiring. That alone was $85. I just never put it together that those things counted.”
That was the smaller discovery. The larger one involved her student loans. Rosalind has been making payments on her graduate school debt since 2005 — over two decades of monthly installments. In 2025, she paid approximately $2,180 in interest alone. The IRS student loan interest deduction allows taxpayers to deduct up to $2,500 in qualified student loan interest, and for married couples filing jointly, the income phase-out for 2025 begins at $155,000 — well above the Underwoods’ $117,000 combined income.
She had never claimed it. Not once.
Why She Had Missed It — and Why That’s More Common Than People Think
When I asked Rosalind how she had overlooked this deduction for so many years, her answer was telling. “The software I used would ask if I had student loans, I’d say yes, and then it would ask if I received a 1098-E. I never got one in the mail, so I always said no and moved on.”
This is a common gap. Loan servicers are required to send a Form 1098-E only if $600 or more in interest was paid during the year — but the deduction itself is still available even if the form wasn’t mailed, as long as the taxpayer paid qualifying interest. Rosalind’s servicer had updated its mailing address policy, and her 1098-E forms had been going to an old address for at least three years.
The VITA volunteer walked Rosalind through logging into her servicer’s account right there at the clinic. The 2025 interest total: $2,180. Combined with the $300 educator deduction, her adjusted gross income dropped meaningfully — and her refund jumped from the $340 she had expected to approximately $2,640.
Looking Ahead: The American Opportunity Credit and What Comes Next
Rosalind’s son Marcus starts college in August 2026. That means when she files her 2026 tax return — the one due in April 2027 — she may become eligible for the American Opportunity Tax Credit (AOTC), which is worth up to $2,500 per eligible student for the first four years of higher education.
Unlike a deduction, which reduces taxable income, the AOTC is a credit — meaning it reduces the actual tax owed dollar for dollar. Up to $1,000 of it is refundable, which means even taxpayers who owe nothing can receive a partial payment.
The VITA volunteer printed out a summary of these credits and handed it to Rosalind, explaining that she should keep it for next year’s filing. Rosalind folded it carefully into her manila folder. “I’ll probably laminate it,” she told me with a small laugh. “That’s the teacher in me.”
The Regret She Couldn’t Quite Shake
After the appointment, Rosalind and I talked for another twenty minutes in the parking lot. She was grateful — that part was clear. But there was an undercurrent of frustration in how she spoke about the years she had filed on her own, convinced she was doing it right.
“I think about what I paid into those loans over the years and never deducted a dollar of interest,” she said. “Even if it was just a few hundred dollars a year, over ten years that’s real money. That’s Marcus’s textbooks. That’s a car repair.”
She’s not wrong to feel that way. If Rosalind paid roughly $2,000 in student loan interest annually for the past ten years and never claimed the deduction, the cumulative tax benefit she forfeited — depending on her marginal rate — could conservatively approach $4,000 to $5,000 over that period. That number is impossible to recover now. The IRS generally allows amended returns only three years back.
That assumption — that middle-income earners are somehow disqualified from relief programs — is one of the most persistent and costly misconceptions in American tax filing. Many of the above-the-line deductions available to teachers and student loan borrowers have income thresholds well above what most households earn, yet the perception of ineligibility keeps people from ever checking.
Before we parted ways, I asked Rosalind what she planned to do with the additional refund. She paused for a moment. “Put it toward Marcus’s first semester,” she said. “What else would I do with it?” That answer — instinctively redirecting a windfall toward her child’s future — said more about her than any tax form could.
Rosalind Underwood is not a cautionary tale about financial recklessness. She is a careful, hard-working woman who was let down by a system that assumes people will find the benefits on their own. The fact that she finally found them — at 62, in a plastic chair at a community center, because she took a chance on a free clinic — is something worth remembering the next time someone tells you the tax code doesn’t work for ordinary people.
Sometimes it does. You just have to know where to look, and sometimes you need someone sitting beside you to point.
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