10 Absurdly Clever Tax Deductions That Got Approved

The IRS has seen some pretty wild tax deduction attempts over the years, and some of them actually worked! Check out our list of the 10 craziest tax deductions you have ever heard of! And if you’re a freelancer, don’t miss our other blog: “The Freelancer’s Guide to Tax Deductions.” Table of Contents 10 Wild Tax Deductions Legit Deduction or Wishful Thinking? Let’s Find Out! Now that you’ve seen some of the most surprising tax deductions that actually got approved, it’s time to test your own deduction savvy. Below are a few expenses. For each, one scenario is deductible, and the other isn’t. Can you determine which is which?Cat FoodScenario 1: Junkyard owner buys food for rat-patrolling felinesScenario 2: Snack for a pet catGuard DogScenario 1: Business guard dog expensesScenario 2: Pet dog expensesTutorsScenario 1: Specialized tutor for a child with a diagnosed learning disability, as recommended by their doctorScenario 2: Reading tutor for general academic improvementAfrican SafariScenario 1: Dairy business owners on a wild animal-focused tripScenario 2: Family vacationPrivate AirplaneScenario 1: Condo owners flying themselves to check on their rental propertyScenario 2: Vegas private jet ride Personal TrainerScenario 1: Trainer for a professional athleteScenario 2: Gym-goer getting ready for summerClown CostumesScenario 1: Professional clown costumeScenario 2: Halloween costumeSun ProtectionScenario 1: Sunscreen for carpenters/gardenersScenario 2: Sunscreen for beach trip Absolutely right! Scenario 1 is deductible, but Scenario 2 isn’t. Many of these cases are based on real stories, proving that the same expense can be approved or denied depending on the context and whether it meets the IRS rule of ‘ordinary and necessary.’ “Ordinary” means it’s common in your line of work, and “necessary” means it’s helpful and appropriate for your business—not just something you want. Tax deductions come with rules. For example, guard dog expenses are only deductible for the time the dog is actually working, and medical deductions are subject to limitations like the 7.5% AGI rule. Because tax laws are complex, it’s always best to consult a professional when in doubt. Itemized Deduction vs. Standard Deduction These unusual (and sometimes surprisingly successful) deductions highlight the importance of understanding the rules and keeping meticulous records. Navigating the tax code can be tricky, and knowing what qualifies as a legitimate deduction is crucial for any taxpayer. This is especially crucial when deciding whether to itemize or take the standard deduction. The TCJA changed the tax landscape, making the standard deduction the better option for most taxpayers. But if you have significant deductible expenses, itemizing can still work in your favor. The good news? The old deduction limit is gone, so you can claim the full amount if eligible. That said, with fewer people itemizing, the IRS is paying closer attention to those who do. If you’re planning to itemize, make sure your records are solid. Looking to keep your records organized and ready for tax filing? Schedule a call with our experts today for bookkeeping support.