IRS TAX PROBLEMS: Disorganization is no defense in Tax Court!
Kevin Rego • June 17, 2024
Tax Court did not find a disorganized "shoebox" compelling which leads to a big liability
San Mateo, CA:
In a recent US Tax Court case, the Wrights' (owners of a couple of small businesses--catering and construction) learned a very important lesson in document organization.
The Wrights were audited by the IRS for their 2014-2016 tax returns. A substantial portion of their business expenses were disallowed by the IRS for lack of substantiation. A total of $46,680 in tax and $9,335 in accuracy-related penalties were charged by the IRS.
The Wrights, feeling that their case was worthy of an appeal, petitioned the US Tax Court to hear their case.
The Wrights presented the Tax Court with 44 exhibits and almost 2,000 pages of documents (receipts, invoices, etc). So far so good....except, many of the receipts and adding machine tapes did not add up to the amounts claimed on their returns. In addition, an additional $58,473 in income was "found" on the catering business bank records of deposits. The documents presented to the court were disorganized, with handwritten notes in the margins, and double entries in the documents (a credit card record showing meal expense and a restaurant bill showing the same expense counted twice). There were multiple instances of inconsistences in the documents, leading the court to question the genuineness of the evidence offered--even noting that some entries appeared to be fabricated.
The Wrights were warned by the judge beforehand that a clear and concise spreadsheet of expenses being claimed would be necessary to present as evidence. Essentially, a "shoebox" of disorganized and jumbled documents were not acceptable. Unfortunately for the Wrights, they did not take that advice.
In the end, after reviewing the mess that he was presented, the judge found the Wrights did not meet their burden of proof. Because of the finding by the court of fabrication and questioning the genuineness of some of the records, the court further found that the Wrights' credibility was so damaged, that their uncorroborated testimony was essentially disregarded. The Wrights' lost their appeal.
Running a business is really no different than an individual tax return. The numbers on the tax return must be "backed up" to substantiate any expense deduction. An organized, clear, and complete record of those substantiations are necessary----putting them in "messy shoebox" and expecting the IRS or Tax Court to fix your organizational deficiency will lead to a bad result for you.
Kevin Rego
www.regotaxlaw.com
San Mateo, CA I usually write about IRS tax problems since my practice centers around IRS collection and audit resolution , however every once in a while some interesting tax and financial related items come across my desk that I think are worth mentioning. If you have kids in high school looking ahead to college or kids in college looking at graduate school and you are wondering--how will I pay for this---this is article is for you. Student Loan Changes are in effect: Starting this July, the way students borrow money for college and graduate school is getting a significant overhaul. New rules will reshape borrowing limits, phase out certain loan types entirely, and for the first time, draw a sharper line between graduate and professional degrees when deciding how much a student can take on. Most of these changes kick in July 1, 2026, and affect federal loans first disbursed for the 2026–2027 academic year. If your kids are already in school, take a breath — many of these rules won't touch you. They're largely aimed at incoming students. Undergraduate borrowing? Nothing changes. For all the commotion surrounding these program reforms, undergraduate loan limits are staying exactly where they've been. Federal Direct Loans remain the main-stay of student aid for four-year programs, and the annual caps haven't moved. Here's a basic breakdown: Dependent students can borrow up to $5,500 in their first year, $6,500 in their second, and $7,500 annually after that. Independent students get more room — $9,500 in year one, $10,500 in year two, and $12,500 per year from there on. Lifetime caps sit at $31,000 for dependent students and $57,500 for independent ones. These numbers haven't budged in years, and since they're not tied to inflation, they now cover a noticeably smaller slice of what college actually costs than they once did. Dependent or Independent--What does that mean: Whether a student qualifies as "independent" matters quite a bit here, since that status unlocks higher limits. Under Section 480(d) of the Higher Education Act, you're considered independent if you're 24 or older, married, have dependents of your own, are enrolled in a graduate or professional program, have served in the military, are an emancipated minor or ward of the court, grew up in foster care, or are a homeless youth — among a few other qualifying circumstances. Because loans rarely cover the full bill anyway, most undergraduates piece together the rest through scholarships, grants, family contributions, 529 savings plans, part-time jobs, and sometimes Parent PLUS or private loans. Graduate students are facing the biggest changes. This is where the 2026 reforms really have a bite. Under the old system, graduate students could stack Direct Loans on top of Graduate PLUS Loans, which allowed borrowing all the way up to the cost of attendance — tuition, housing, food, everything. That flexibility is gone . Graduate PLUS Loans are being eliminated for new borrowers. Going forward, most graduate students will be limited to $20,500 per year, with a lifetime cap of $100,000 for all graduate borrowing. There is an exception carved out for a narrow tier of professional degrees: medicine, dentistry, law, and a few others. Those students can borrow up to $50,000 per year and $200,000 over the course of their studies. Worth noting: unlike before, these new caps aren't pegged to the cost of attendance. That means federal loans may no longer stretch far enough to cover both tuition and living expenses, leaving students to find other ways to fill the gap. Families borrowing through Parent PLUS loans will feel it too. The changes don't stop with students. Parent PLUS loans — long used as an additional source of college funds— are also getting capped. Where parents could previously borrow up to the full cost of attendance, they'll now be limited to $20,000 per year per child, with a lifetime ceiling of $65,000 per student. Since these loans land on the parent's credit and the parent is responsible for repayment, families who've relied heavily on Parent PLUS to afford higher-cost schools may find themselves rethinking their options. Scholarships, savings, and more affordable educational pathways are likely to become a bigger part of the conversation going forward. Have questions about how this affects your family? These changes may not show up on a tax return, but they're very much a part of your financial picture. Where loans in the past have made up a large part of financing college tuition and living expenses, new changes may limit those options. Remember to always verify your circumstances with a college financial planner or college advisor. These are general provisions designed as an overview of changes. Your individual circumstances may vary. Kevin Rego Law Office of Kevin Rego 650.933.5222 Disclaimer: The information provided is intended to provide a general overview of the topic presented at the time of publication. Tax laws change and you should always consult a tax professional for the latest tax law. This article is not intended to be a legal interpretation of your individual tax or legal situation. If there is a conflict between the information provided and any legal authority implementing or interpreting the topic, the legal authority shall prevail. Always seek legal advice from a licensed attorney. This article does not in any way establish an attorney-client relationship. That relationship can only be accomplished with both parties signing a mutual, written agreement.
A recent U.S. Tax Court case is a cautionary tale every taxpayer who takes a charitable donation deduction on their annual tax return needs to hear. A couple donated a piece of land worth thousands of dollars to their city in the state of Utah. They had letters, a deed, city council records — a whole file of documents showing the donation was legitimate. They filed their tax return with the donation deduction and that is when things went haywire. The IRS disallowed the entire deduction. In subsequent litigation challenging the disallowance, the US Tax Court agreed with the IRS. Not because the donation was not real. Not because the land had no value. But because the paperwork did not say the right things. Here is what you need to know to protect your deduction. The Magic Number Is $250 If your charitable contribution — cash or property — is $250 or more, the IRS requires a Contemporaneous Written Acknowledgment (CWA) from the charity. “Contemporaneous” means you must have this document (1) on or before the date you file your return or (2) the due date of the tax return — whichever is earlier. Without it, if your charitable deduction is challenged by the IRS, your deduction is likely gone. What the Letter MUST Contain Under I.R.C. § 170(f)(8)(B), the CWA must include all three of the following: A description of what you donated. For cash, state the dollar amount. For property, describe what was received by the charity. The charity does not need to state the value — but they must describe what they got from you. An affirmative statement about whether the charity gave you anything in return for the donation. This is the one that trips up ALOT of taxpayers. If the charity gave you nothing — no dinner, no tickets, no tote bag — the letter must say so explicitly. Words like “donation” or "thank you" or "acknowlegement" or “gift” are not enough. The required language is simple: “No goods or services, in whole or in part, were provided in exchange for this contribution.” Silence on this point will cost you your deduction. If the charity DID give you something in return for the donation, it must be described and include an estimate of the value of what you received. For example: “Two gala dinner tickets with an estimated fair market value of $150 were provided in return for your charitable donation of $500”. For contributions to religious organizations or houses of worship, a statement to the effect of such goods or services consist solely of "intangible religious benefits" is often appropriate in this part. Close Is Not Good Enough In many areas of tax law there is a concept called substantial compliance — meaning if you got close enough, the IRS would cut you some slack. That doctrine does not apply here. The CWA requirements are strict, and a deduction will be disallowed in its entirety if the letter falls short — even if the donation was completely genuine and legitimate, like our couple from Utah. Before You File — Make sure everything is in order If you have made a significant charitable contribution and are not certain your acknowledgment letter meets the IRS requirements, contact the qualified charity before you file. It is far easier to get a revised or re-worded letter from the charity before your return goes in than to fight the IRS afterwards. If you've received an IRS letter or notice that and you're not sure what to do next, contact my office today for a consultation. Kevin Rego Law Office of Kevin Rego 650.933.5222 Disclaimer: The information provided is intended to provide a general overview of the topic presented at the time of publication. Tax laws change and you should always consult a tax professional for the latest tax law. This article is not intended to be a legal interpretation of your individual tax or legal situation. If there is a conflict between the information provided and any legal authority implementing or interpreting the topic, the legal authority shall prevail. Always seek legal advice from a licensed attorney. This article does not in any way establish an attorney-client relationship. That relationship can only be accomplished with both parties signing a mutual, written agreement.