The following is a true narrative. Names and identifying details have been changed to protect confidentiality.
David Klein didn’t set out to violate federal law. He just needed to make payroll.
I met David when he called our office in a panic. As executive director of Rofeh Services, a nonprofit that helps families navigate medical crises, he was used to managing cash flow problems. But this time, he was staring down the IRS.
The core problem was simple. Rofeh didn’t have enough money to cover its operating expenses. Payroll, rent, vendor bills—the numbers didn’t work. The only liquid funds in the account were the payroll taxes that had already been withheld from employee paychecks: federal income tax, Social Security, and Medicare. That money was supposed to go to the IRS. It was set aside, held in trust.
But David needed to keep the lights on, and the staff paid.
So, he used it.
Over the course of several months, he dipped into the withheld trust funds whenever cash got tight. Just enough to keep payroll going. Each time, he told himself it was temporary—that he’d make it right once funding stabilized. It wasn’t a scheme. It wasn’t theft in his mind. It was survival. A way to buy time.
But the reprieve he was counting on never materialized. Instead, a letter from the IRS arrived.
Rofeh Services owed over $350,000 to the IRS. But the bigger blow came in a second envelope. David himself had been named. The IRS viewed his actions not as a bookkeeping shortcut but as a deliberate misuse of federal funds. Under IRC §6672, they held him personally liable for the entire trust portion. And if they concluded that his decision was willful and knowing, they could escalate the case beyond civil penalties—all the way to felony prosecution, with real prison time on the table.
This is what most people miss. Payroll taxes aren’t just another line item. They don’t belong to the organization. They don’t even belong to the employer. They are held in trust and using them for anything else—even for reasons that feel justified—can trigger personal and criminal exposure.
When I saw the facts, I moved his file to the top of my stack. This was no longer a collections issue. It was a crisis.
First, we stabilized the situation. All future payroll taxes were filed and paid on time. The IRS doesn’t negotiate while you’re still violating.
Next, we ran the numbers. The trust fund portion—the part that exposed David personally—was significant. There was no way to pay in full. Our best move was to file for an Offer in Compromise (OIC).
The OIC process is a grind. Weeks of document gathering, financial disclosures, and IRS scrutiny. Our top priority was keeping David out of a courtroom—or worse. One element gave us a clear path to do that.
By default, when a taxpayer submits a payment toward an outstanding tax balance, the IRS applies it however they see fit—typically to penalties and interest first. But a little-known provision allows taxpayers to designate how voluntary payments are applied. Under Rev. Rul. 79-284, the IRS is required to honor that designation if made clearly. What most people don’t know is that you can even designate an OIC 20% payment towards the trust fund only. By directing the payment to the trust fund portion, we immediately eliminated David’s personal exposure.
When we submitted the designation, the Revenue Officer pushed back. She insisted that you can’t designate an initial OIC payment towards the trust fund only and that the IRS would apply the payment at its discretion, regardless of what we requested.
We didn’t press the issue. The law was clear, and we were confident in our position—but our priority wasn’t to win an argument. It was to keep our client out of court, and out of prison. Preserving a productive relationship with the IRS was essential to that goal.
We gave her the space to reconsider without forcing a confrontation.
“That’s surprising,” I said. “The Offer in Compromise form and the Internal Revenue Manual seem to permit it. Can you walk us through your position?”
Two days later, they reversed course. The payment was applied as directed. David was out of the blast zone.
What followed was slow and procedural—paperwork, correspondence, and the final approval. But the danger had passed. David was no longer at risk of indictment. He could walk into his office without wondering if it might be his last day there.
Today, Rofeh is still running, continuing its mission to help families navigate complex medical crises. David is still at the helm. But the experience reshaped how he thinks about risk, responsibility, and the limits of good intentions. This isn’t just a cautionary tale—it’s a reminder that following the rules is only part of the story. When you find yourself in a bind, it’s knowing how to work within the system that can make all the difference.
This material has been prepared for informational purposes only, and is not intended to provide or be relied upon for legal or tax advice. If you have any specific legal or tax questions regarding this content or related issues, please consult with your professional legal or tax advisor.
