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The Weirdest Tax Deductions That Actually Worked (No, Your Dog Is Still Not One of Them)

January 13, 2026 by Bill Bourbonnais

Every tax season, Americans ask the same hopeful question: “Can I deduct that?” Sometimes the answer is “no, sorry.” Sometimes the answer is “absolutely not, please stop talking.” But every once in a while, the answer is: Shockingly . . . yes. Welcome to the wild side of the tax code, where deductions roam free, logic occasionally takes a lunch break, and the IRS reluctantly admits, “Fine. We’ll allow it.”

Filed Under: IRS, taxes Tagged With: business deductions, CPA humor, entrepreneur finance, financial strategy, IRS approved, small business taxes, tax deductions, tax planning, tax strategy, tax tips

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