Kiplinger

18 Nice-Try Tax Breaks Rejected by the IRS

Over the years, taxpayers have concocted a lot of zany arguments to justify their tax breaks. We've come up with 18 of the most creative ones that the courts decided did not quite work.

As secret agent Maxwell Smart would say, "Missed it by that much!"


My Little Princess

Getty Images

A couple's daughter began competing in beauty pageants at age 9. She won between $1,000 and $2,000 in prize money each year that was deposited into her college savings account. The parents reported the income on their returns and also took large write-offs for the cost of travel, costumes and other expenses.

Because the prize winnings were compensation for the child's services in the pageant, they are included in her income. And only she can deduct the costs, even though the expenditures were made by the parents. So the Tax Court denied the parents' deductions.

A Little Peace and Quiet

Thinkstock

A busy tax preparer ran her business from her home. During tax season, she felt so harassed from clients calling her at all hours of

You’re reading a preview, subscribe to read more.

More from Kiplinger

Kiplinger5 min read
As the Market Falls, New Retirees Need a Plan
Anyone newly retired or nearly so must feel like they have the worst timing in the world. A portfolio tends to be largest near retirement, just before those savings are about to be drawn down. These days, however, most portfolios have lost value; the
Kiplinger2 min read
Fed Rate Hike Meets Expectations, But What Next? Here's What the Experts Say
The Federal Reserve served up a widely expected third consecutive jumbo rate hike when it concluded its regularly scheduled two-day meeting on Wednesday. Chair Jerome Powell and the rest of the Federal Open Market Committee (FOMC) raised the federal
Kiplinger4 min read
Got Crypto? The IRS Really Wants to Know
The 2022 crypto price crash understandably has some investors concerned. But for those of you who haven’t run for the hills, it’s worth knowing that cryptocurrency currently has the attention of not only the Biden administration, and Congress, but th

Related Books & Audiobooks