People Reveal the Biggest Loophole They’ve Ever Taken Advantage Of

Photo Courtesy: Paul Bradbury/OJO Images/Getty Images

In many cases, rules serve as guidelines for the proper way of doing things, and most of us don't question them too much. However, in the age of the internet, we're constantly learning about “life hacks” that could make our days a whole lot easier. Despite these acceptable shortcuts, sometimes opportunities spring up that allow us to take advantage of situations in ways the people who created the rules just didn't anticipate. And they're just too good to pass up — as the following cunning and crafty people know all too well.

Are these loophole exploiters sneaky or strategic? You decide.

Advantage in the Arcade

The arcade near where I used to live as a kid had an air hockey table in the back room. Somebody figured out that if you jimmied the coin slot a certain way, you could get an extra three or four games with a single quarter. None of us had much money, so this was a lifesaver. The employees didn’t really care because whatever money we did have was typically spent at the snack bar, so they made money off of us anyway.

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I kind of miss that place. They always had free watermelon for kids who had absolutely no money. Nobody felt left out.

Free Big Macs on Demand

Back when the McDonald’s app first came out it didn’t require a login. When you first downloaded it, you got a free signature sandwich. I would just delete the app and re-download it every time I was hungry.

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Turning Salads Into Sandwiches

My college campus had a cafe with a deli and salad bar, and the deli sandwiches were way overpriced. A standard turkey sandwich was like $8. The salads, on the other hand, were very reasonable. Most of them only cost $1.50 each.

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I discovered that the salads had all the same ingredients as the sandwiches. The only difference was that the meat in the salads was shredded. The deli sold slices of bread for 25 cents each, so I would just buy the bread, load it up with a salad and grab some free mayo and mustard packets. Everything would cost just under $2. I used that trick for my two years of college.

Prizes for the Psychic

A local radio station had a contest where you would win a prize if you called in after they had played songs by the same artist back to back. I went to their website and saw that they had a “now playing” feature and an “up next” feature. My girlfriend at the time would start calling in before the second song even came on. She won tons of prizes, ranging from concert tickets to a laptop.

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The Winning Cap

Back in the ’90s, Dr. Pepper ran a promotion where you could win stuff from the bottle caps, including a free Dr. Pepper. I learned that you could look up into the bottle and kind of make out what was written on the inside of the cap. I bought one Dr. Pepper and continued to “win” many more Dr. Peppers. As a teen, having an unlimited supply of soda was amazing.

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Hawaiian Hallways

At my high school, we had to wear a button-down shirt and tie to class every day. One of the kids realized that they never specified what kind of button-down shirt it had to be, so he chose to wear Hawaiian shirts every day to class. Technically, it met the dress code so it stuck.

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Pretty soon, most of the school started wearing Hawaiian shirts with ties to class. We looked like a bunch of ridiculous Jimmy-Buffet-goes-Mormon types, but it was worth it to spite the system. They changed the rule to ban Hawaiian shirts soon after.

Gift Card to Down Under

A few years back, an online store had a promotion where whoever spent the most money over a month would get free round-trip airplane tickets to anywhere in the world. My friend found out that you could buy gift certificates on the site. So, he bought a $25 gift certificate and would use it to buy another $25 gift certificate. He repeated this spending pattern, and in the end, he ended up spending only $25 for round-trip tickets to Australia.

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The Very Lucky Vending Machine

I found a vending machine at work that didn’t differentiate between quarters and golden dollar coins when dispensing change; when it was supposed to give you quarters about half of them were golden dollars. I put in as many $5 bills as possible and bought the cheapest item available. I got $8 of change back each time. My total profit off that machine was over $50 before it ran out of golden dollars.

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Outsmarting the Teacher

In third grade, our teacher had to leave the room for some kind of emergency and left one of the students in charge. The teacher told us that we were not allowed to talk while she was gone. If we did, we would have to write the line “I will not talk in class when instructed not to” 100 times on sheet paper.

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Well, my friend and I were bored, so we started writing out the punishment. When we were finished, we proceeded to talk to each other until the teacher returned. The student left in charge wasn’t sure what to do. It was hilarious.

Refunded for Rough Streaming Quality

Not exactly a giant loophole, but I used to live in a very rural area with really slow internet. Anyway, I’d rent movies on Amazon and stream them and the definition would get pretty rough sometimes. It’d have to buffer a bit, but overall not enough to ruin a movie for me. Well, Amazon will refund you if rented a movie and it gets a notice that the streaming wasn’t great. I rented a whole bunch of movies I normally would never pay to rent and got refunded for all of them. Yes, I was sacrificing quality, but I basically had a “free” streaming service until I moved and got better internet.

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Sole Scholarship Applicant

Back in the ’60s, the school district in my hometown was broken up and absorbed into the surrounding district. Fast forward to 2003, when I was applying to colleges. I discovered that there was a scholarship fund for people who used to live in that district. The district was long gone by then, but the scholarship still existed! I applied and got the scholarship. I don’t think there were any other applicants.

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Thank You for Holding

The old call center I worked at made it very clear that calls shorter than two minutes and greater than 15 would never get listened to by QA (which to their credit was accurate the entire time I worked there ).

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All that meant was that those of us who had a mean person we didn’t want to deal with could just put a caller on hold for 5-10 minutes for no reason as we “looked into that” for them. Then we could hang up the call with no possible repercussions.

They never saw how bad of an idea that was — at least up until the time I left.

Same Course, Different Credit

I took a course in college that ended up being offered the following year under a different course number. The course descriptions and lesson plans were basically identical, but because the course number was different, it counted as a new credit. I signed up, never attended a class, took the final and got another credit.

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Expensing Expired Items

Not sure if it’s a loophole exactly, but a grocery store chain used to have a policy that if you found an item on the sales floor that was expired, they would give you an equivalent item for free. So in college, me, my roommate and my girlfriend would go to the grocery store at midnight and go through the meat, dairy and bread sections looking for things that had just expired due to the change in date. I had discovered that they didn’t go around pulling newly expired items until around 5:00 a.m. We would consistently roll up to the register with a cart full of chicken, steak, bread and cheeses, all for free. They hated us, but it was their rule.

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Cashin’ In on Trash

I was working maintenance at McDonald’s during the time that they had a Best Buy bucks promotion. Large sodas and large fries had scratch-offs worth at least $1 at Best Buy. I would go through the trash daily and pull out all the discarded scratch-offs that were never scratched.

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I was able to "buy" myself a free computer that year using only the scratch-offs that I collected. I felt bad for the cashier at Best Buy, though. She had to manually scan each scratch-off and verify the dollar amount.

Sliding by With Sonic Receipts

Sonic had a “Free Route 44 with the completion of a survey” promo about 10 years ago or so. By complete accident, I found out that the survey codes for the free drink weren’t just printed on the receipts given with meals – they were printed on every receipt.

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For at least a month, I’d go to Sonic before work and redeem my free Route 44 coupon and then ask for a receipt of the transaction. I got a new survey code every single time. I also got probably 20 free Route 44s before someone higher up caught on and killed the promotion. I’m sure they lost a ton of money on that loophole.

Pass to the Underground

At my university, a parking pass was $200 a month. You needed to use the parking pass to gain access to the underground lot, which was heated. Long story short, we figured out the parking passes had a magnetic strip on the back that was useless because the machines would read the barcodes at the top.

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Six of my friends bought parking passes, photocopied them and glued the barcodes over the tops of older membership cards. It ended up costing us just $30 a month. It was the best year of my life. We live in Canada, so underground heated parking in the winter was the dream.

Slow and Steady

When I was a kid, my town had a “slow bike race” tournament. The objective was to cross the finish line in the last place and to keep your balance during the entire race. The rules stated that each time your foot hit the ground, five seconds would be subtracted from your time. However, they didn’t say anything about keeping your foot planted on the ground.

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Once the race started, I just stood and waited until everyone else was close to finishing, then just rode across the finish line.

Being Book Smart

In my high school, we had a rule where if you lost your book, you would be provided a new one. If you didn’t return the book before the end of the school year, you would have to pay for it.

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In the first few weeks, I “lost” my books. Over time, I built up a stack of books at home and in my locker. I never had to drag around a heavy backpack.

Skipping for Saturday School

My high school required students to attend a certain minimal number of classes a year in order to graduate. If you missed too many days, they made you go to “Saturday School” to make up for the missed days. But Saturday School was great — they were just half-days and you could sit around quietly reading a book.

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I realized that they didn’t keep track of when you were absent and when you did Saturday School. So I just attended every Saturday School to build up credit so I could skip days later in the year whenever I wanted.

A Promotion Worth Milking

At my college, they offer a promotion with a certain brand of milk bottles. You can buy one for $4 and return the empty bottle for $2. Well, I recently found out that the grocery store by my girlfriend’s dorm sells the exact same brand of milk for $2 a bottle.

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A Super Bowl Win

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

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Moving a Reservation

I travel a lot and lose tons of money canceling hotel reservations last second. Instead of accepting the penalty for canceling last second, I “move” my reservation to three days later. Then I call back in a few minutes to fully cancel my reservation at no charge.

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Calling Out Sick

I once worked at a call center that would let you call out two days in a row as long as it was for the same reason and only counted it as one absence. Their thinking was most people could use two days when they call out sick but are afraid to take it and that makes more people sick. What most people did was realize they could call out between their split days off and give themselves a four day weekend. They asked a girl once why she always took two days off and she said, “You give me the option and you’re surprised when I take it?”

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The Super Senior

Ask for a new college ID card the day before graduation and you’ll get a college ID card that won’t expire for the next four years. That means building access isn’t revoked and you’ll have access to the brand new bathrooms to use on football game days. They’re clean and warm. It’s worth it, trust me.

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Haggling With Hulu

A friend of mine has had free Hulu for over a year and a half now. He got one free month and went online to cancel it. However, every time he clicked to cancel, the system would offer him another free month to stay. Last I talked to him, it was still working.

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All You Can Eat, All Winter

Back when I was homeless, I found this newly opened place that was a 24-hour all you can eat buffet. Yeah, I guess they didn’t think that through.

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I went there, paid the $9.95 and just spent the entire winter in a warm restaurant, on a soft sofa bench, eating and drinking very slowly and occasionally going to the bathroom for a sponge bath. Totally beats sleeping outside in the snow.

Utilizing Uber Promo Credits

I earned hundreds of dollars in Uber credits. When Uber launched in my country, I changed my personal referral code to “Uber[country].” My hope was that people without a code would guess at a promo code and go with the obvious. I had dozens of people use the code to get the “$10 off your first ride” promo without my ever sharing the code. They got $10, and so did I.

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Hacking Higher Education

When I transferred to another university, I had to go to each department and explain my credits. The advisor would then assign the appropriate courses for those credits. They never checked my previous course descriptions, so basically if I knew the course descriptions at the new university, I could convert my old credits to whatever I wanted.

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I managed to swap some courses around and inflate a grade or two into something better.

Call Waiting

I used to work at a call center that employed a dialing program. I figured out that if I hit a series of functions on the dialer in the correct order, it would freeze up the program and I’d have to restart my computer, which took about a half hour.

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I did it a couple of times to get some free time at work, but others caught on and the company eventually fixed the program with an update.

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