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12 of the most bizarre tax deductions that are actually legal

12 unusual tax deductions you can actually file for
Posted at 2:05 PM, Apr 12, 2024

It’s the most un-wonderful time of the year! Tax season.

While few people like this annual process, take heart: You may have some interesting little tax deductions hiding in plain sight that could boost your return or reduce the amount you owe.

Here’s a short list of unusual deductions people have successfully claimed in the past. Some of them are hilariously obscure, but others might make sense for your family — if you qualify, of course.

1. Ransomware Attack

If you’ve been the victim of a cyberattack and paid money as “ransom” to get out of it, you can claim the amount lost as a tax deduction. Law enforcement experts recommend that victims not pay any ransoms, but if you do, this is a “silver lining.” Yay?

2. New Swimming Pool

Medical expenses are a very broad category for tax deductions. Care bills, prescriptions, equipment and appointment costs can all be used as tax deductions. And, yes, that includes a home swimming pool, if your doctor can provide documentation that it’s medically necessary. (And not just for summer fun.) However, you must show these expenses exceeded 7.5% of your adjusted income for the year to claim any medical deduction.

3. Clarinet Lessons

Learning the old licorice stick can save you money on your taxes! Back in the 1960s, a family successfully argued that their kid’s orthodontist recommended clarinet lessons to help fix an overbite. So if you can get an orthodontist to declare them necessary, you may be in luck. (Full disclosure: As a former clarinet player, I must say this seems … unlikely. But it’s worth a shot.)

A young girl plays clarinet
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4. Personal Protection Animal

You can claim a guard dog as an expense if it helps protest the premises of your business. Vet bills, chow and training could all be deducted with proper documentation. However, be advised that the dog’s breed does matter. The IRS authorities will not be amused if they’re greeted by your lovebug golden retriever — and not a Belgian Malinois on patrol — if they audit you.

MORE: Tax crunch time is here: What to do (and not do) this week

5. Cosmetic Surgery

Like many of these, this is a tricky deduction to qualify for. But it’s possible if you’re employed in certain industries. In 1994, a dancer claimed her breast implants as a deduction because they were required for her to make money. The courts agreed, likening the implants to a costume.

A doctor holds silicone breast implants
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6. Free Beer (For Others, Not You)

Here’s another one that could fall under business expenses, if you’re so inclined. A gas station owner once successfully claimed that his free beer giveaway was an expense that attracted customers. (One would imagine, however, that providing free beer at a gas station is not a smart move for other, more important reasons.)

7. Expenses For Volunteer Work

Besides the personal satisfaction you get from giving your time, you can also claim certain expenses incurred while volunteering. These include gas money, uniform costs and even the cost of entertaining a donor on behalf of a charity (seems like yet another way to claim beer). You can also deduct travel costs like airfare, hotel and taxi fare if you traveled to volunteer — as long as there isn’t “a significant element of personal pleasure” involved. So try not to have too much fun.

A young woman organizes clothing donations in a box
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8. Whaling Boat Expenses

Calling Captain Ahab! You can deduct up to $10,000 a year for repairs on your whaling vessel! But whaling is extremely illegal in the U.S., so this is only available to certain Native American groups who practice whaling as a tribal tradition.

9. Exceptional Trees (Hawaii Only)

Hawaii honors conservation with a unique tax deduction. If you have a special tree on your property, you can qualify for a state tax deduction to cover its care — up to $3,000 every three years. What trees are considered “special”? The criteria are generous, including trees that are especially large, old or pretty, or have cultural value. Anyone can nominate a tree to be declared “exceptional,” but professional arborists make the final determination.

a large banyan tree next to a lake
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10. Donated Deer Meat (South Carolina and Maryland Only)

Two other states offer an unusual incentive to help feed hungry citizens: A tax credit for donating venison. In Maryland, hunters can get $50 for each deer carcass they butcher and donate, up to $200 per year. It’s also $50 in South Carolina, but only professional meat processors qualify for the credit there, not the hunters themselves.

11. Lawn Care Expenses

This one counts if you run a business out of your home — but you have to demonstrate that your house is your workplace and that a manicured lawn is relevant to your business. One man who pulled this off successfully showed that he met clients at his home, requiring him to keep his lawn in good shape.

Man mowing a lawn
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12. Continuing Your Education

Folks who love learning can get a tax credit for educational expenses, even if they’re not seeking a degree. The Lifetime Learning Tax Credit offers up to $2,000 in credit for tuition, fees and expenses at a post-secondary institution. That means you can take that college-level painting class you’ve wanted to try and get a nice little tax reimbursement the following year.

As with all things related to taxes, there are caveats and loopholes aplenty, plus serious documentation requirements. Don’t try to claim things without the evidence to back it up — the IRS isn’t known for its forgiving nature, and the costs of hiring a tax attorney will likely eliminate any gains earned from making an iffy claim.


12 of the most bizarre tax deductions that are actually legal originally appeared on Simplemost.com