Clever People Share The Biggest Loopholes They’ve Ever Found

February 12, 2019 | Scott Mazza

Clever People Share The Biggest Loopholes They’ve Ever Found

Loopholes are some of the greatest life hacks out there. When someone discovers a minor detail about a rule or policy that allows them to get way more out of it than was ever intended, or even to do the very opposite of what it exists for, the feeling can be pretty awesome. While loopholes can cause legal philosophers to pore over the true meaning of the letter of the law versus its spirit, they just cause the rest of us to be thankful for the creative minds who discover them. Here are 42 stories of some of the most epic loopholes people have ever discovered and taken full advantage of.

1. Around the World with $25

A few years back, an online store had this promotion where whoever spent the most money over a month would get free round trip plane tickets to anywhere in the world. My friend (who's a genius) found out that you could buy gift certificates on the site. So he bought a $25 gift certificate and spent it on another $25 gift certificate. He then repeated this process over and over again until he had won the contest.

So he ended up spending $25 on round trip tickets to Australia.

Loopholes Facts310sw

2. The Fashion Business

I went to a Catholic school with uniforms. However, if we earned a “jeans day” pass, we could be exempt from the uniform for a day. The passes were always different colors, including white. I took one white pass to a copier and copied enough to fill out one page, then printed one full page of passes, then printed mass stacks of pages. I made a lot of money selling them out.

Loopholes FactsFlickr nloik

3. Two for the Price of Zero

At my school, a parking permit is $220 for a car and $30 for a motorcycle. However, you can add a car as a second vehicle to your motorcycle permit, since it rains sometimes. I have my fair share of friends I've let know about this trick.

Loopholes FactsNational Park Service

4. A Medium to Large Loophole

I used to work at Papa John’s to help pay my way through college. There was a contest we had where if you got someone to "upsize" their pizza from a medium to a large for an extra $2, you got points towards movie tickets. A large was simply $2 extra normally anyways. So anytime someone ordered a large to begin with, I simply put in a medium and "upsized" it.

I won every single week. My coworkers didn't notice this obvious loophole and it didn't cost the customer anything extra, so I didn't have a problem with the moral gray area. Free movie tickets every week was a huge plus in college.

Beyoncé Knowles factsPxHere

5. I Knew You Were Trouble When You Didn’t Walk In

My high school had a stupid rule that banned you from attending prom if you had a Saturday detention that semester. I got in trouble and was assigned to one, but my girlfriend really wanted to go to prom. I just kept skipping it and they kept adding more until they rolled it into a day of actual suspension.

They had no rule barring you from prom for an out-of-school suspension, so I got a day off and took my girl to prom.

Loopholes FactsFlickr

6. Happy Birthdays!

As a teenager, I created 12 email accounts with different birthdays and got promotional free birthday ice cream cones every month of the year.

Tom Hanks FactsPexels

7. Parked Cards

My brother got free parking for pretty much his entire time at university. It was during that golden period when parking meters were able to accept credit cards, but before they were actually connected. They'd read a card and check it against a locally stored list of banned numbers, and once a month the meter maid would download the transactions, process them, and update the blacklist.

My brother found that they'd accept prepaid gift cards if they were backed by Visa or MasterCard, but couldn't check the available balance, so he'd buy one, use the balance up on whatever, then use the card for parking until the end of the month when it'd get processed, be found to not have funds, and be banned. Rinse and repeat. Guy saved probably $2,500 over his degree.

Loopholes FactsShutterstock

8. Buy One, Get All Free

They used to have a promotion at Wendy’s, probably 6 or 7 years ago, where if you filled a survey out on your receipt you could get a free burger next time. I guess they didn’t notice that you could take the survey again on the receipt of the free burger, and just keep getting free ones each time. So we would go every day after school and chain five free burgers after buying just one. We did that for a few days until they finally caught on and stopped accepting it.

Loopholes FactsWikipedia

9. Pool Shark

My brother once yelled, "Last one in the pool is a rotten egg" and then immediately jumped into the pool. However, I realized that if just never jumped in, then technically he would be the last one in the pool—making him, and not me, the rotten egg.

Kids Share the Most Humiliating Acts FactsShutterstock

10. Take Me to Your Leader

At my company, I have two bosses who don’t interact with one another, but who have equal authority over me and my job. When neither assigns me any work for the day, the other doesn’t know, and just assumes that if I’m not asking, I’m doing something for the other. Without the company ever suspecting a thing, I've gotten paid for spending entire days at home doing nothing while each thinks I'm working for the other.

Human Psychology FactsShutterstock

11. All the Tea in China

I can't remember when it happened, but it was years ago. I think it was Nestea or some other canned tea, but if you bought a case of tea then there was a coupon on the box for a free case—except it was on every case, so now you have case #2 and another free case coupon. All the tea could be had.

Really That Stupid factsFlickr

12. Measures of Success

My high school offered a bunch of incentives for getting the most improved score on a standardized test. So I failed on purpose the first year I did it, then tried for real the following year. I received both a reserved parking spot and a special card allowing me to leave the campus for lunch whenever I wanted.

Quiz: MonarchiesMax Pixel

13. The Answer is Blowing in the Wind

When I was in high school, I applied for a summer job with the county. As part of the "unbiased" application process, each applicant was asked to take an intelligence test. The test consisted of about 80 questions. Each question was four or five line drawings, and you had to put an X in the box next to the one that didn't belong. Pretty easy.

I happened to notice, though, that the test paper had two parts, and that an answer key for marking the tests was attached at the back with a sheet of carbon paper in between. I could peel the sheets apart and look inside. So, I did all of the questions with obvious answers and, if I was unsure, I just peeled the paper apart, noted the answer on the second sheet, and made sure I got it right.

Of course, I got 100%. I figure that if you can cheat on an intelligence test, you're pretty smart.

Criminal Minds FactsShutterstock

14. Do It Yourself

If you want a quarter pounder at McDonald’s but don’t want to pay the price, you can just order a McDouble on a sesame seed bun and add the other condiments of a quarter pounder.

Loopholes FactsWikipedia

15. Juicy Earnings

There was a drink machine in college that charged $0.75 for a juice. If you put a dollar in, it gave you five quarters in change. I got a juice every day for months before they finally fixed it.

Tokyo FactsGetty Images

16. By My Calculations, This is a Loophole

In keyboarding, we had to type up a huge table and do the math for each problem. I went into Excel, typed the formulas up, and copied/pasted it onto a sheet as a table. Cut an hour off of doing it manually. This was in seventh grade and my teacher was pissed because "I manipulated the rules".

My thoughts were that it was more convenient and easier, and in the real world, that's what I would do.

Evil People Who Made History QuizShutterstock

17. Premium Loophole

My dad figured out a good one back in the 80s. Back then cable companies would give you a free weekend trial of a premium channel hoping you would then want to sign up and pay. However, our cable company's method of giving you access to the special channel was to send a signal to your cable box, which unlocked the channel. To turn off the channel at the end of the free trial, another signal was sent.

My dad figured out that the signal to lock it was only sent for a short period of time, so before the end of the free weekend, he would unplug the cable box and then plug it back in the next day. Since the box never got the signal, we would have a free premium channel for a while.

House M.D factsPixabay

18. Ahead of the Game

Some American colleges don't understand the British or European education systems, and that's how people like me manage to get into college at 16. Best decision ever.

Emma Watson factsShutterstock

19. Scratch That Off the List

I was working maintenance at McDonald's when they did a Best Buy bucks promotion. Large sodas and large fries had a scratch-off that was worth at least $1 at Best Buy. I would go through the trash daily, pulling out all the discarded scratch-offs. I got a free computer that year for Christmas. I also had the poor cashier at Best Buy in tears. She had to manually scan each scratch-off and verify the dollar amount.

Loopholes FactsFlickr Ian Muttoo

20. Doing the Time, Doing the Crime

In third grade, our teacher had to leave the room for some kind of emergency and she left one of the students in charge. The teacher said that we were not allowed to talk, and if we did, we would have to write "I will not talk in class when instructed not to" out 100 times. Well, my friend and I were bored, so we started writing out the "punishment" and when we were finished, proceeded to talk to each other until the teacher returned.

The student left in charge wasn't sure what to do. It was hilarious.

Students in class chatting.Getty Images

21. Poetic Justice?

I used an illegal downloading service to illegally download a more expensive premium version of itself for free.

Awkward Conversations to Translate factsPexels

22. Netflix, But No Chill

Unfortunately, the American version of Netflix isn’t available in other countries. However, I've discovered that if I turn my free VPN app on and off ten times and then open up Netflix, I'm able to watch American Netflix without the annoying notification that 'blocks' my VPN. And it I get that notification, all I have to do is quit the Netflix app, smash the VPN button a couple more times, and reopen it. Works like a charm.

Evil People Who Made History QuizShutterstock

23. That’s What You’d Do for a Hoodie

My university was trying to encourage people to walk, so if we downloaded a specific health tracker that was connected to our school account, it would convert steps into points. The points would get you stuff like free coffee, mugs, and—last but not least—the most expensive prize: a university hoodie, which cost about £30. Now, the health tracking app was pretty basic.

It wouldn't let you log your steps manually, however it would let you connect with other health apps. I found a health app that would let me add in steps and I logged in an equivalent of 50 km a day and, in a few days of logging manually, I would get myself a hoodie or two and never get caught. However, I told my friend about it, and he really perfected the method of getting more steps a day.

Apparently, there was a hidden physical limit to how far a person can walk in a day, but he managed to trick it by setting his height to be 1 cm since the shorter you are, the more steps you need to take to cover the same distance. In the end he claimed about 10+ hoodies and he would just get them for anyone who asked.

Loopholes FactsPixabay

24. Works Well With Others

Teacher: “For this project you will work in groups of less than seven.”

Me: “Sir, one is less than seven.”

Teacher: “Ok, fine. Do it all yourself then.”

I got 70% on this assignment—the highest mark I ever got in group work.

Lawyers Share “I Rest My Case” FactsShutterstock

25. Decoded

For a while, McDonald’s had a promo where, when you walked in, you could scan a QR code and possibly get free food. However, different locations and different cutouts had different codes. I took pics of as many unique codes I could find, put them all on a handy PDF, and scanned them all using an Android device and an IOS device before lunch.

I got free extra value meals regularly. In fact, I still had a couple free ones left over when they stopped the promotion.

Loopholes FactsMax Pixel

26. Slow Poke

When I was a kid, my town had a "slow bike race" tournament. The objective was to cross the finish line in last place, and the key is to keep your balance. Well, the rules stated that each time your foot hit the ground you would have five seconds subtracted from your time. But it didn't say anything about keeping your foot planted on the ground. So once the race started, I just stood there and waited until everyone else finished, waited a good five seconds after that, then just rode across the finish line.

Loopholes FactsMax Pixel

27. I Like Those Odds

Back in 2013, Papa John’s had a promo for the Super Bowl where if you called the coin toss correctly, you would get a voucher for a free one-topping pizza. However, the only control in place was that you could only enter the contest one time per email address. I created more than 60 emails, half of them calling heads, half tails. Ate free pizzas for six weeks.

Loopholes FactsWikipedia

28. Lost and Found

We parked our rental in a parking lot in Santa Monica for a week. A 24-hour stay was around $25, but there was also a “lost ticket” option for $10. Not sure how, but I lost my ticket every day.

Introverts Avoid Human Interaction factsPixabay

29. What Rhymes with Orange? How About 3 More Oranges!

Our local Tesco accidentally had two offers for Terry's Chocolate Oranges at once, so if you bought 4 (or a multiple of 4) they GAVE you 50 pounds on your card. I tried not to abuse it so that they wouldn’t notice and change it, but I bought 4 chocolate oranges with other stuff through the self-checkout every day for almost 2 weeks before they corrected it.

I planned to save them for Christmas presents, but you know how delicious Terry's Chocolate Oranges are...

Loopholes FactsWikimedia Commons User:Blutackey

30. Schooled

Amazon lets you get a free 3-month prime trial with a .edu email account. My university lets you create unlimited aliases for your email account.

Loopholes FactsPixabay

31. Never Let School Interfere With Your Education

Took a test run of a course the school was planning to offer in the future when I was in college. Easy enough course, got my credit, went home happy. Next semester the course went "live" and was offered under a different course number—but the description was identical. Signed up, never attended a class, took the final, and got my credit again.

Fire Me, I Dare You factsShutterstock

32. Hello, I Must Be Going

My local parking garage gives you a ticket when you pull in that you have to take over to a machine to pay for before you leave. The amount you pay is based on how long you were parked and the gate at the exit will only open when you insert a ticket that says it has been paid for. Whenever I go into the garage, I get a ticket, go over to the machine, and immediately pay.

It only charges for a few minutes, then I park there for eight hours for free.

Childish Behavior From Adults factsPixabay

33. Quick Maths

Back in the day, two five-piece chicken nuggets orders at Burger King cost less than one eight-piece chicken nuggets order. Me and those two extra nuggets were laughing all the way to the piggy bank.

Loopholes FactsWikimedia Commons

34. Time On My Hands

My old job had a loophole about time. It worked as such. If you were scheduled for an 8 AM shift, you had 7 minutes to arrive and still be counted as on time. If you arrived past the 7 minutes, you were considered 15 minutes late. Loophole: it worked the same for clocking out. If you stayed and helped for an extra 7 minutes, you automatically got an extra 15 minutes of pay.

During my tenure there, I would always ask if people needed extra help—and made sure I stayed past the 7 minutes. This went on for a full year. Got probably close to an extra 24 hours of pay.

Human Psychology FactsShutterstock

35. Location, Location, Location

Back in the 1960s, the school district in my hometown was broken up and absorbed into the surrounding districts. Fast forward to 2003. I'm applying to colleges. I discovered that there is a scholarship fund for people living in that old district's area. The district is gone, but the scholarship still exists! I applied and got the scholarship. I don't think there were any other applicants.

Julia Roberts QuizShutterstock

36. Regifting

A friend of mine works for a popular store where she gets a 40% off employee discount on everything. We realized this 40% off deal also applies to gift cards. So I have her get tons of them for me, then I sell them online and give her a cut.

Loopholes FactsShutterstock

37. The Original Candy Crush

An Italian restaurant my family loved had a candy claw machine that we played every time we went. The trick to learn was that if the claw closed all the way, it thought that meant you didn't get anything—and would let you play till it thought you did get something. This meant that we could go for individual items that would fit into the claw perfectly (like one sucker, one laffy taffy).

So by going for one small item at a time instead of a big pile, we actually ended up getting more. The best part? IT ONLY COST A QUARTER! They no longer have that machine though…

Loopholes FactsFlickr Steven Depolo

38. Let it Snow!

Instead of buying sandbags to weigh down the bed of my pickup truck in winter, I just shovel the snow right in there. When it warms up, the snow melts. No muss, no fuss.

It'll be a cold day in hell when I actually pay for a bag of sand.

The American Civil War FactsPixabay

39. A Minor Crime Spree

Michigan used to have a law forbidding minors from pleading guilty to a crime without a lawyer. I found this out by accident when I was 13, and used it three more times before I was an adult. What happens is that I, as a minor, would just plead guilty, they would then give me a sentencing date and let me leave. Then a week or so later I would get a letter stating that it is not legal for me to plead guilty without a lawyer and that my case was dismissed or thrown out because of it. I got out of three minor possession tickets that way.

History’s Greatest Mistresses quizShutterstock

40. Aloha!

I went to a strict high school where the dress code said we had to wear a button down shirt to class every day. One of the kids realized that they never specified what kind of button down it had to be—so he showed up in a short sleeve Hawaiian shirt one day and, since it technically met the policy standards, he was in the clear. Pretty soon, most of the school started wearing Hawaiian shirts to class.

We looked like a bunch of ridiculous idiots, but it was worth it to spite the system and be slightly more comfortable. They changed the rule to ban Hawaiian shirts shortly after.

Loopholes FactsWikimedia Commons

41. Hard Work Pays Off

When it comes to loopholes, there is nothing crazier than what you can discover when you take the excessive amount of time necessary to put all details of a store’s policies and coupons together. My wife is the coupon queen. The kind you would hate to be stuck behind in a store. Her strategy is kind of genius, to be honest.

Apparently, the way to get the best deals is to wait until you can find store coupons, manufacturer coupons, and sales all on the same item. Then you go and clear the shelves out of that item. It's so embarrassing, I can't even go with her. The cashiers always argue and say that you can't use all three together, but they are wrong.

My wife has the store policies printed out and readily available in a binder that she shows them in the store. Not joking. She really does that. She's even part of a community where a bunch of wives all mail each other coupons and trade them like Pokemon cards. It's insane. The cashiers and other customers hate her so much, but she does get riiiidiculous deals on things in bulk this way.

Like, a year’s supply of laundry detergent for $20. She's insane, but it's hard to argue with the results.

Wildest Things Found Inside Houses factsPixabay

42. What’s Good for the Goose is Good for the Gander

I had an agreement with an employer which said that if I stayed with them until a certain date, they would pay for my school tuition. If I willingly left before the date, though, I would have to pay the money all back to them. The parent company of my division changed after the agreement was signed and the time came for me to get the cash I was owed.

The head of HR refused to pay. I went to him and asked why I wasn't getting the check we had agreed to. He stated that the agreement was with the previous parent company and therefore was no longer valid. He had this smug look on his face, but then he noticed I had a big smile on my face. I could tell he couldn't figure out why. I asked him again if they were refusing to pay and he said yes.

I then stated that I no longer have anything binding me here, because the contract stated that "If I willingly leave the company, I have to repay the money." He agreed and asked what my point was. I then stated that if the parent company did change then I did leave said company, but I did not willingly leave. Therefore, I did not owe any money if I left this company, as it was not the company I signed the agreement with.

The expression on his face changed. I continued on with, "If I, hypothetically, put my two weeks notice in now, I would be able to leave without owing any money." It didn't take him long. He realized that by stating that the agreement was no longer valid for his own purposes, he had given me a way out of the contract. So he agreed to pay me the money.

Spoiler alert: he was fired just a few weeks later for various reasons. He was one of the worst HR directors I have ever seen.

Men's Secrets factsPixabay

Sources: Reddit,

More from Factinate

Featured Article

My mom never told me how her best friend died. Years later, I was using her phone when I made an utterly chilling discovery.

Dark Family Secrets

Dark Family Secrets Exposed

Nothing stays hidden forever—and these dark family secrets are proof that when the truth comes out, it can range from devastating to utterly chilling.
April 8, 2020 Samantha Henman

Featured Article

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.

Madame de Pompadour Facts

Entrancing Facts About Madame de Pompadour, France's Most Powerful Mistress

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.
December 7, 2018 Kyle Climans

More from Factinate

Featured Article

I tried to get my ex-wife served with divorce papers. I knew that she was going to take it badly, but I had no idea about the insane lengths she would go to just to get revenge and mess with my life.

These People Got Genius Revenges

When someone really pushes our buttons, we'd like to think that we'd hold our head high and turn the other cheek, but revenge is so, so sweet.
April 22, 2020 Scott Mazza

Featured Article

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but few people know her even darker history.

Catherine of Aragon Facts

Tragic Facts About Catherine of Aragon, Henry VIII’s First Wife

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but very few people know her even darker history.
June 7, 2018 Christine Tran

Dear reader,

Want to tell us to write facts on a topic? We’re always looking for your input! Please reach out to us to let us know what you’re interested in reading. Your suggestions can be as general or specific as you like, from “Life” to “Compact Cars and Trucks” to “A Subspecies of Capybara Called Hydrochoerus Isthmius.” We’ll get our writers on it because we want to create articles on the topics you’re interested in. Please submit feedback to Thanks for your time!

Do you question the accuracy of a fact you just read? At Factinate, we’re dedicated to getting things right. Our credibility is the turbo-charged engine of our success. We want our readers to trust us. Our editors are instructed to fact check thoroughly, including finding at least three references for each fact. However, despite our best efforts, we sometimes miss the mark. When we do, we depend on our loyal, helpful readers to point out how we can do better. Please let us know if a fact we’ve published is inaccurate (or even if you just suspect it’s inaccurate) by reaching out to us at Thanks for your help!

Warmest regards,

The Factinate team

Want to learn something new every day?

Join thousands of others and start your morning with our Fact Of The Day newsletter.

Thank you!

Error, please try again.