Crazy tax deductions: When they don’t – and do! – work

July 11, 2020

Tax-deductions-header_Shannon-Ryan

You’re working on your tax return and discover that you are that close to shaving a few more dollars off what you owe Uncle Sam.

Many in this situation are tempted to get creative. Don’t. The Internal Revenue Service has seen it all. OK, most of it.

The bottom line is that sketchy tax deduction claims are invitations to IRS auditors.

Crazy and possibly costly tax break claims: Earlier this year before Tax Day got pushed to July 15 by coronavirus precautions, Washington Post financial columnist Michelle Singletary talked with some tax professionals about the wild write-offs they’ve seen.

Singletary cites some of those brazen tax fudging ideas in her article “People try to claim the darnedest tax deductions to reduce their bills.”

I won’t spoil the article, which is one of this weekend’s Saturday Shout Out honorees, but yes, many of them involve so-called business claims. And I suggest you check out the readers’ comments, too.

Some odd, but OK tax deductions: Now I’m not saying don’t deduct, just do so wisely and within the law. Even the IRS says you can and should take all the tax breaks to which you are legally — I repeat, legally — entitled.

And there are some tax deductions that look at first glance to be a bit iffy, but to which the IRS said, OK.

Matt D’Angelo details just such situations in his Business News Daily article “Crazy Tax Deductions Allowed by the IRS.” That piece earns this weekend’s second Saturday Shout Out.

The IRS’ maybe/maybe not decisions when it comes to curious tax deductions also prompted Shannon Ryan, a Certified Financial Planner, to provide a visual tax write-off take. The image at the top of this post is from Ryan’s crazy tax deductions infographic, which get this weekend’s third shout out. 

Audit implications: Also remember that when you do claim anything, be it a commonly accepted tax deduction or one where you’re a little aggressive, be sure to have the documentation to back it up if the federal tax collector does eventually raise an eyebrow.

When it comes to audits, it’s the opposite of our legal system. The IRS presumes you cheated and you have to prove that you most definitely didn’t. If you can’t, you’ll end up owing not just more tax, but also penalties and interest.

So consider your quirky claims carefully.

You also might find these items of interest:

Advertisements

 





 

Share:

The More Tax Posts tab at the top of this page will take you to, well, more tax posts. You also can search below for a tax topic. 

Latest Posts
The latest Dirty Dozen tax scam list is familiar because too many are still falling for the schemes

March 5, 2026

Tax filing season is also peak time for tax scams. Be on the lookout for…

Read More
Hello Tax Season 2026

Happy New Tax Year! Are you ready to file your 2025 tax return? I know, too early to ask. But Tax Day 2026 will be here before we realize it. The Internal Revenue Service deadline to file and pay any tax we owe is the regular April 15 date this year. It’s also Tax Day for most of the states that collect income taxes from their residents, which is most of the states! If that seems too far away right now, don’t worry. As is the case every tax season, the ol’ blog’s tips and other tax reminders should help all of us meet our state and federal responsibilities. Procrastinators also will want to keep an eye on the countdown clock just below. It tracks how much time we have until April’s Tax Day, just in case we put off our annual tax task until the absolutely final hours and decide we need to instead get an extension request into the IRS by that date. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

Comments
Leave the first comment