It was supposed to be a quick tax payment. But for one Bay Area couple, it turned into a costly mistake that left them with a penalty and a lot of stress.
How can a simple check-writing error cost you thousands?
This all started when Joy and Kenneth Hays wanted to get ahead on their taxes. They were trying to pay their 2025 estimated tax early — a smart move, right? Their estimated amount was $3,360. But here’s where things went sideways.
Joy wrote $3,360 in the box where you write the numbers but in the line where you write the amount in words, she accidentally wrote “thirty-three thousand + 60.” That single slip turned a regular check into a $33,060 tax payment.
And the IRS? They tried to take the full amount.
What happens when a check bounces twice?
Because their account obviously did not have $33,000 in it — “I would have bought a car!” Joy said — the check bounced. And not just once. Twice.
That led to a lot of confusion. The couple says Chase Bank told them they only process the written amount in words, not the number box. That meant the IRS tried to collect more than what was in the account.
And here is the crazy part:
- The IRS did not catch the mistake.
- They cashed the check anyway.
- The check bounced — twice.
- Then the IRS hit the couple with a $661 penalty.
You would think someone — anyone — would notice something was off.
Why did the IRS charge them a penalty?
The IRS claimed it was an underpayment or late payment. But it may have also been from the bounced checks. That part is still unclear.
Kenneth said, “I just figured it was impossible… You’d think someone would look at the check and realize that it was wrong.”
Unfortunately, tax attorney Chris Housh says that is not how it works these days.
- The payment processing and tax processing departments are separate
- The check gets separated from the tax forms
- No one compares the number box to the written amount
That is how a $30,000 overpayment mistake was not caught.
How hard is it to reach the IRS for help?
Joy and Kenneth tried everything to fix the issue. They called the IRS for weeks. Sometimes they sat on hold for six hours, only to be disconnected.
- No one returned their calls
- No one reached out from the IRS
- They still have not gotten a real answer
“The IRS — they need more people!” Joy said.
What should you do if this happens to you?
Tax attorney Housh gave some helpful tips for others who find themselves in a similar situation:
- Try calling the IRS late in the day, when call lines are less busy depending on your time zone
- Go in person to a local IRS office if phone support does not work
- As a last resort, write a letter explaining your situation
But even letters are not a quick fix. That department is also understaffed and overwhelmed, Housh said.
He warns that these kinds of issues may become more common due to recent policy changes that put more burden on fewer IRS workers.
Can the IRS really ignore obvious mistakes?
Sadly, yes. Mistakes like this happen “often enough,” Housh said. And the system is just not built to double-check small details like what is written in the amount line of a check.
As Kenneth put it, “Is it all AI?”
It might feel that way. But it is really just a system stretched too thin — where humans are no longer catching obvious red flags.
And until things change, regular folks like Joy and Kenneth are left to deal with penalties for honest mistakes… and spend weeks trying to get someone — anyone — on the phone
