Real Life Loopholes That Were Successfully Exploited

Real Life Loopholes That Were Successfully Exploited


They say it's important to work smart, not hard. Sometimes following the rules doesn't necessarily mean doing things the same way as everyone else, and if you can figure out how to game the system in your favor you can feel like a true genius.

Here are some real life examples of people who found amazing loopholes and got their money's worth out of broken promotions.

Cereal Killer


Back in college we found a loophole with coupons at Kroger for General Mills cereal. If you bought 4 boxes of cereal each box was a dollar. But if you did the self checkout you would be printed out a coupon for $4 off your next purchase.

We used the loophole to buy about 300 boxes of cereal. We only spent $12 on all of it. We would've spent less but we had to go to another Kroger once the manager got wind of us.

We kept around 20 boxes for ourselves and donated the rest to the local food bank. They were so excited when we showed up with three vehicles full of cereal. Totally worth the $12 and all the time it took.

Story credit: Reddit / RoiVampire

Password Saboteur


I used to play a lot of backgammon in Yahoo Games - and some people were real jerks when losing. Most commonly they'd stall the game by taking the maximum 5 minutes per move, hoping I'd resign. I learned a way to boot these people off Yahoo for as long as I wanted, by trying to log into their account.

When I used the wrong password ten times, the account was locked for 24 hours. They couldn't log in again until I chose to allow it.

Story credit: Reddit / Scrappy_Larue

The Eternal Coupon


I got a flier in the mail one day from a pizza joint advertising 5 dollar large pizzas on certain days of the week with a code that was valid for another month.

I'm still using the code to this day, three years later. It's only worked at the local branch so far, but I've been riding that gravy train as hard as possible.

Story credit: Reddit / Solias

The Amazing World of Gumball


By accident I found a gumball machine if you turned the dial really slow it would drop the gumball, then you could dial it back just enough so the next gumball would drop into the tumbler bits, then slowly dial forward again until it drops, etc.

Got about 20 of them and stopped when I realized that I really didn't want to chew that much cheap gum…

Story credit: Reddit / Kifenstein


Obvious Winner


Back when you could win a free coke under the bottle cap, I spotted a pattern where the caps that I won had a logo on the top that looked faded, whereas the losers all looked pristine.

For 2 weeks, everyday after school I'd stop at the UDF and exchange yesterday's cap for a new coke.

Story credit: Reddit / avec_aspartame

A-Meow-Zing Savings


A few years ago, there was a promotional sample of catfood. The bag cost 3 dollars and it had a 3 dollar coupon inside it. The coupon did not have a weight limit on it.

So I bought a big plastic bin, put it in my trunk, and for an hour, went in and out of the store filling that plastic bin, one $3 bag of cat food at a time, cashing in the 3 dollar coupon the previous bag gave me.

Story credit: Reddit / avec_aspartame

Endless Screentime


When I Was younger (12-13) I had one of those stupid timers on the computer that would only let me use the computer 2 hours a day before I got kicked.

Found out that if you minimize the screen alerting you that you have ran out of time, you never run out of time. Best summer ever.

Story credit: Reddit / NOT_ah_BOT

Easy A


This past semester, I needed to take a Biology class with a lab to graduate. I was told that it was one of the easiest classes at my school to take, but as a lit type, I didn't agree much.

It was so much information all at once, and I found it really boring, so I didn't do so well on the tests or assignments. I got Cs and Ds, even on the final which I stayed up all night to study for. We also had a class blog.

There were about a hundred and twenty of us, and we each had to write three posts per semester on anything biology-related. I didn't do well in the lab section, either. I failed the multiple choice test and the practical, and I assumed I was done for.

However, the professor said that if we made comments on our peers' blog posts, and turned in worksheets to show what edits we made, when, and on what topic, we could get five extra points per edit. Most kids did two or three. I did 97. Got an A for the semester.

Story credit: Reddit / doublementh

Wonder Why They Went Out of Business?


So I wanted to get cheap coffee filters online as I knew i was going to need them for the foreseeable future and wanted to get a better price on them. So I found a site that had them at half price ($1.95 for 100 filters, usually $3.99 at the store) what I was paying at the store and put them in my cart.

When I went to check out it asked me if I wanted to setup an automatic delivery to have them shipped every 2 weeks and they would reduce the price.

I said sure why not, after all they were the cheapest i had found and getting them every week would mean i didn't have to keep ordering them. So it brought the price down by like to like $1 for 100 filters. I was thrilled. Then it asked me if i wanted to join the Coffee savers program for more discounts!

I said sure! So after joining the savers program it brought the price down to $0.00. I was stunned. I still had to add my credit card but I was never charged.

So for 2 years I got 100 filters delivered to my door for free. Never got charged NOT ONCE. One day though I got a notice that said they were going out of business and my free filters would end.

I was sad. But the stock pile I amassed them lasted me about 2 years and recently in the past 2 weeks I had to buy new filters. Life will never be the same.

Story credit: Reddit / maramok

Rescuing the Princess


A long long time ago Hostess chips (was the major brand in Canada at the time) had a Mario Bros promo. You got a "bingo" card in each bag of chips and every card was a winner. You had to scratch 3 of 9 areas and if you matched the icons you won.

One of my friends figured out that using a tin can with a tiny hole punched in the bottom and then dropped down unto a 100W lightbulb, you could see through the card and find the winning spots to scratch.

This spread around town and a week later there wasn't a single bag of chips to be found anywhere. Sold out all over town. We all had garbage bags of open chips around. I won 1 grand prize which was a Super Mario Bros game.

Story credit: Reddit / Frozen-assets


Refresh Rate


There was a site where you could upload your own games and make revenue for every time someone visited the page. Turns out just refreshing the page counted as a visit, so I found an auto refresher and left it on 24/7.

I made almost $2,000 before they figured out what was happening and now it only works from different IP addresses.

Story credit: Reddit / halfwizard

Empty Guarantee


Back when Hollywood Video was around, they would guarantee new releases to be in stock. If they rented out all of their copies in the store then they would give you a voucher for a free rental.

I was in college at the time and would go into the store near my college campus at around 10pm on a Friday night. There was simply no way for them to have any copies left by that time, so I would collect whichever vouchers were available. Rinse, repeat. Cheaper than redbox.

Story credit: Reddit / Ragina_Falange

The Golden Ratio


A Blockbuster video near my house had a giant gumball machine near the cash that had special gumball-sized plastic orbs that instead had a free movie/game rental. So for 25 cents, you had the chance to win a $4.99 rental.

Well this was around for my entire childhood till one day I walked past the machine and noticed it was almost empty, and it looked like the remaining ratio of gumballs to free-passes was like 3:1.

When they first filled the machine years ago, apparently the employees just tossed all the passes on top and barely mixed it up. I came back with a stack of quarters and for $10 I got like 17 free rentals and 23 gumballs. The rentals lasted a few months, the gumballs lasted a few days.

Story credit: Reddit / SovAtman

Very Big Gulp


Several years ago, 7-11 ran a promotion where all of the Big Gulp cups had a sticker on them that had some kind of prize on them.

The sticker had those little, wavy blue and red lines that you had to look at through 3D glasses to read, so, in theory, you had no idea what you had won until the clerk looked at it at checkout. Most of the prizes were crap - stuff like 25 cents off of a sketchy hot dog.

But, one of the prizes was a free Big Gulp, so if you got that one, your Big Gulp was free. I memorized the pattern of blue and red lines, fished through the cups until I got the right one and got free soda pop for about two months until the promotion ended. Excuse me while I go check my insulin…

Story credit: Reddit / Troutmandoo

Cancel Culture

Real-Life-Loopholes-Successfully-Exploited-15.jpg.optimal.jpgWikimedia Commons / RFMONLINE.DE / CC 4.0

When vending machines first started accepting credit cards you could swipe your card, select a drink and when the little drink pod starts moving to collect your drink hit cancel.

The cancel button would stop the card transaction but not the machine so you could get free drinks. Was a sad day when it stopped working.

Story credit: Reddit / oshaneo

Army of Peeps

resizePink_peeps.jpg.optimal.jpgWikimedia Commons / Jon Sullivan / Public Domain

Around Halloween, Peeps website had a code to get 20% off at checkout for any order. It ended up working on all items, including gift cards. So I first bought a $3 gift card, then I used that gift card to by a $4 gift card etc. until I got to an $80 gift card.

I then bought $80 worth of peeps with $3. I told one of my friends and he did the same thing but got his gift card up to $1,600.

Story credit: Reddit / sasha28


The Sketchiest AirBnb


My friend works for a company where he spends the entire week traveling and staying in hotels and he can expense any hotel. Because of this my roommate and I listed our air mattress on Airbnb for $150 and he's the only one that ever stays there.

He's only even in town once every couple weeks but whenever he is we have a small house party entirely on the company's dime!

Story credit: Reddit / panthyren

Student For Life


My college didn't put any dates on our Student IDs. No graduation year, no expiration date, nothing. As a result, I kept using it to get student discounts for YEARS after I graduated, mostly the 15% off J. Crew discount.

Story credit: Reddit / hummingbird4289

Price Match Pandemonium


Probably about 8 months or so ago. K-Mart accidentally ran an online ad where the Playstation 4 was listed for something like $200 cheaper than its MSRP. Since Wal-Mart does price matching, people were taking that ad into Wal-Mart and getting PS4s for really cheap.

Story credit: Reddit / SnowHesher

Hidden in Plain Sight


There was a Papa Johns coupon for 50% off if the official PJ twitter retweeted you. I found the code looking through their website. I got half off pizza for a year and a half.

Story credit: Reddit / Calyxo

Print to Win


Back in the 80s. Raffle for a car had write your own entries. Printed off thousands of pages of entries on my printer. Won car. Unfortunately I was too young to drive. My sister totaled it before I got my license. Easy come...

Story credit: Reddit / Kaell311

Poker Face


Years ago when online poker was a thing in the US, there were sites that let you look at statistics on other players. They'd give you like one free look, but I realized you could just manually change the player's name in the link and get unlimited free statistics from them.

I used it a lot to see if someone was a good player or not before sitting down at tables with $20+ buy ins.

Story credit: Reddit / Ranndym


Low Effort Coffee Card


There's these 3 Dunkin Donuts in my area that let you buy "Coffee Cards" basically you pay 200$ for the card and can come through any part of the day, how ever much you want a day and get an any size coffee for a year.

Well my mom bought one last year and it had expired; she bought another one this year and it looks EXACTLY THE SAME as the old one; They took no effort into changing the card at all, so my mom gave me her old one and I get free coffee whenever I want.

They're not scannable cards or gift cards. It's literally just a pink piece of paper in the shape of a card that has the Dunkin Donuts label on it and the locations where it's valid and a managers signature.

It does have the date it "expires" on there real small but they have never once checked my card, they only ask me to "flash" it at them; so I guess the day they ask to inspect it the jig is up.

Story credit: Reddit / occhiolism

Gaming the System


Worked at Wal-Mart. Employees can't take advantage of mismatched prices. See 3DSXL labeled at $70, when they first came out. Friend is with me. Hand him money to pay for it. Get new 3DSXL for $70.

Story credit: Reddit / Bonemonster

Large Tea Refills


At my local movie theater, you could get a small drink for $2.50 or a large drink for $3.50, and large gets unlimited refills. Or you could get a SoBe tea for $2.50. But they didn't give you the SoBe bottle because they wanted to avoid any broken glass incidents.

So they poured the SoBe into the large cup. Boom: unlimited large drink refills. I saved several dollars that way.

Story credit: Reddit / r2d2sthirdleg

Copay Double-Up


My son attends speech and occupational therapy every week. Usually it is a $35 copay for each therapy, but if I do them on the same day I only have to pay the copay once. Saves me about $140 a month!

Story credit: Reddit / SurroundedByCrazy789

The Battle of Hastings


There used to be an electronics store called 'Hastings' where I grew up that sold both new and used electronics. They had a deal that if you traded in 3 used games of a common type (e.g. all ps2 games) you could get a brand new game for free, no strings attached, just free, any game of that system.

So I would go into the store buy 3 incredibly cheap used games (bass pro hunting or whatever it was called for 5$, they had dozens) and then walk out, double back, and then trade those in for a $60 brand new game.

I did this constantly for a few months while being harrassed by the managers there until they stopped the promotion.

Story credit: Reddit / [deleted]

Mischief Managed


In elementary school we had the Accelerated Reading (AR) program. You would read a book, take a test on the computer, and be awarded points based on how well you did. At the end of the year you could buy things at the book store with the points you accumulated.

I had just finished reading Harry Potter and the Prisoner of Azkaban and got a perfect score on the test. The computer was only supposed to allow you to take the test once but I figured out you could take that specific Harry Potter book unlimited times. I racked up so many points and was never found out.

Story credit: Reddit / saucecat2

Blowing Up


I worked in a call center during college. Our main performance measure was the number of donations solicited PER CONTACT. If the person didn't answer or hung up immediately, it didn't count against you.

I discovered a bug where, if I blew into the microphone just as the phone started to ring, it would register in the computer system as a no-answer and dial the next number. I rode this out for several months before I got tired of blowing my microphone for 8 hours a day and quit.

Story credit: Reddit / smokebreak

Dumpster Diving


In the 80's Chuck E Cheeses didn't shred the tickets you get out of their games and use to buy toys, candy etc. My friends and I were biking one day behind a strip mall practicing our wheelies and jumps. We saw a worker throwing a garbage bag of tickets into the dumpster behind Chuck E Cheese.

We grabbed it and then started circling back about once a week. Garbage bags and garbage bags full of tickets. We were doing so well, one of my friends parents got in on it.

She would take the mini van behind there and have her kids load up. And this is why tickets are now shredded. I think I still have a huge stockpile of frisbees and stuffed animals in my parent's attic somewhere.

Story credit: Reddit / bboy1977

Replacement Refund


Bought an old sega Genesis game, I think it was some flight sim which was the crappiest game I ever played. So I took it back to K-mart and got told "No refunds for opened games. Replacement for the same one if broken."

Annoyed that I couldn't get my money back I said it was broken and went for the replacement. They handed me a new copy of the game and my original receipt.

Left and came back an hour later, "I want a refund for this game, here is my receipt and unopened game." Got my money back, went and bought a different old Genesis game.

Story credit: Reddit / FOTBWN

Party of One


I was once the only person to show up to a Microsoft CRM event, since I was the only person to attend I automatically won the door prize of a Xbox 360 with a Kinect.

The downside of this loophole was 3 long hours of talking with MS product evangelists who were very disheartened and desperate to make a sale.

Story credit: Reddit / IntrepidusX

Dollar Trading


I used to work at a small town bank with an ancient computer system. We had a small stash of Canadian currency that we would occasionally exchange for customers free of charge either way.

To do this, we looked up the current exchange rate and used our teller software to give us the value of $XX.XX CAD to USD or vice versa. I found out one day that this exchange rate NEVER updated and was stuck at 0.72 CAD to every 1 USD.

This was back when the USD was lower in value than the CAD. Being the enterprising individual that I was, I exchanged all of my cash (not much at the time, I was 16) for CAD with the excuse that I was going there over the weekend.

Went to a bank down the street and traded that money in for an easy 50% gain or something like that. I did this over and over for at least a year until they finally fixed the issue with the computer.

Story credit: Reddit / flinters17

Forgotten Coupon


In college I bought a pack of coupons for Hungry Howie's Pizza. It had three coupons for a free pizza, no other requirements, just a completely free pizza. I would call and order my pizza, tell them that I had the coupon for a free pizza, show up and "forget" to give them the coupon every time.

I always had it on me as a backup, just in case they did ask for it. But, out of the three coupons, they only asked for it once. I kept using them for months, until the coupons expired, which I am sure they were looking for.

I ended up getting a few dozen free pizzas out of them, which was great for a college student.

Story credit: Reddit / Spe1025

Except in California and Oregon

Real-Life-Loopholes-Successfully-Exploited-35.jpg.optimal.jpgWikimedia Commons / TaurusEmerald / CC 4.0

About 15 years ago, Microsoft had a promotion where you could get a $300 Best Buy shopping spree if you signed up for 3 years of their dial-up internet. Bad deal, right? Until you read the fine print, which said that if canceled, you would be responsible for paying anyway... except in California and Oregon.

I heard about this one day, went to BB the next, and the day after that they shut down the promotion after mobs of people were descending on Best Buy. Got a crap load of Game Boy games, DVDs, and other stuff.

Story credit: Reddit / mercurialchemister

Free Parking


When parking lots originally started accepting credit cards, the machine would just save the card info and the operator would charge the card later. Well, the machine didn't check if the card was expired or not. So.. swipe a cancelled credit card, get free parking.

Story credit: Reddit / ulthrant82

Free Money


They've closed it now but a couple years ago I discovered you could charge an american express 'serve' card with a regular credit card by going to walgreens (or maybe it was rite aid I forget). I have a credit card with 1.5% cash back.

Every month I put $10K on the serve card (that was the limit) and then just paid my cc bill with it. I cleared $150/month for free.

Story credit: Reddit / PM_ME_BAY_AREA_GIRLS

Cheaper Than Fixing the Problem


My '96 Jeep Cherokee used to leak transmission fluid really badly. Luckily, Jiffy Lube offered free "top-offs" on all fluids between oil changes. So I would just pull into Jiffy Lube every couple of weeks and have them fill my transmission fluid back up. They did not like me.

Story credit: Reddit / ShepHeartsTali

Sandwich Shop Deserved This For Being Stingy


I worked at sandwich shop when I was a young lass. We were allowed one free sandwich for the entirety of our employment there. Being an endless pit of hunger 16 year olds are, I was determined to get as many free sandwiches as possible.

If someone called in a phone order and never picked it up, the sandwich was fair game for employees after an hour. So I would text my friends to call in the sandwich I wanted and then never pick it up.

Everyday I got free sandwiches. It was amazing. If I didn't eat it, I would bring it to school the next day and sell it.

Story credit: Reddit / ___Little_Bear___

The Power of eBay


I lived down the street from a rare book store that didn't have a website. I would go in, take pictures of really expensive books, list them on eBay with a reserve of the cost of the book +$50 sometimes they would sell for $500 to $1000 over the price of the book.

Story credit: Reddit / Divotus

Literal Loop Hole


One of my professors let us use one side of a 8.5x11 sheet of paper as a test "cheat sheet", so I cut it and made a mobius strip with it so I could use "both" sides.

Story credit: Reddit / fuzzypyrocat

Button Bashing

Real-Life-Loopholes-Successfully-Exploited-42.jpg.optimal.jpgFlickr / włodi / CC 2.0

Was in a trivia bowl type competition in college. As soon as the announcer began asking the question you could buzz in and answer. If you got the question wrong you lost no points and the question was skipped.

My team answered the first question correctly and proceed to mash the buzzer for the rest of the round, effectively blocking out all the other questions. We won the round with a final score of 1pt. They changed the rules before the next round.

Story credit: Reddit / jdrama418

The House Doesn't Always Win


I was in Costa Rica at a casino, losing money left and right on blackjack. I left the table and went to find my buddy, turns out he was playing casino poker, the kind where you play against the dealer. I had never been interested in it before but I was sick of losing at blackjack in Spanish so I sat down and bet.

I was freaked out the first time it happened because I didn't think it was legal, but all 5 players at the table would compare the cards in their hands before the dealer turned over his. This way we knew if we had a shot at winning with a straight or flush, which paid more, or should fold.

I don't know if the dealer cared or could not understand English, but we all cleaned up at that table over the course of an hour or so. I walked away with over a grand.

Story credit: Reddit / 10per

Location, Location, Location


Currently Citgo has an app that lets you check in to a citgo gas station 10 times to receive $5 off your next purchase. I work next door to citgo and check in every couple hours (there is a 2 hour wait in between check ins). I save at least $10/week on gas.

Story credit: Reddit / 1234567891011twelve

One Way Conversation


We had a person working in tech support where I used to work a long time ago. There was an employee who was low on his call numbers, so management did some research.

They found that he never took any inbound calls, so they started looking at call histories and found that his outbound calls were only 5-10 seconds long. So, they started listening in on his calls.

They found that he was having entire hour-long conversations about fixing various computer and Internet related things with nobody. He'd make the outbound call, then hang up, and then pretend to be talking to the customer. Honestly, it sounds like more work than actually just doing work.

Story credit: Reddit / Nix-geek

Going Gold


I hesitantly bought three bitcoin just as they were going up, then sold one at their peak for the original cost of the three. I've since spent my effectively free bitcoin wealth on the only thing of value one can buy with bitcoin: Reddit Gold. At time of writing, I have gilded 266 posts.

Story credit: Reddit / IronOhki

Redbull Gives You Gas


There was a deal at my local gas station where three cans of Redbull were $7. There was simultaneously a deal where every can of Redbull you bought got you 5c per litre off gas, up to 50 litres. Gas was $2.10 a litre at the time.

I figured out that I could buy 42 cans of Redbull for $98, and get $105 of gas for free. I did this multiple times, and now hate Redbull as a result.

Story credit: Reddit / Joslo88

Multiple No Choice


I had a professor in college who would give partial credit on multiple choice questions. It wasn't something like, show your work and get partial credit, it was circle the correct answer and cross out the wrong answers.

For a question with 4 answers, each wrong answer crossed out was worth 25%. I didn't try it because they were pretty easy tests anyway, but one of my friends tried just crossing out every answer. He got 75% for crossing out all of the wrong answers correctly.

Story credit: Reddit / Spe1025

Coupon Master


Clipped ALL the Sunday "5 dollar off" coupons for the restaurant I waited tables at, every time someone payed cash, i got an extra 5 dollar tip. I made way too much money doing that.

Story credit: Reddit / Billbongers



Growing up I worked at a chain grocery store. They had a policy in place that if an item price label didn’t match the scanned price in the computer, the first item was free and any subsequent items would be for whichever price was lower.

Every few months an elderly woman would come in and spend 4-5 hours shopping. When she would come up to the register, she would have a full cart and near everything would be free. I had to ring her out a handful of times and only caught a few items overall that she was wrong on.

At one point, she found a comforter BBB mislabeled and got it for free ($40-50 sticker price). More than once the store manager would watch her on the store cameras to ensure she wasn’t switching the stickers but never saw her do anything sneaky, just very calmly looking over every item shelved one at a time.

Eventually the policy changed and she stopped coming in at all.

Story credit: Reddit / DrunkPhoenix26

The Deal


Ever since my daughter turned 18, her lifestyle began to change subtly. She always had a knack for being independent, but "ever since she turned 18, she seems to have a lot of money in her bank account." As a parent, it was unsettling. She was in college, didn't work part-time, and the money for her tuition and living expenses were provided by me. The mysterious wealth bothered me. "So, I had no idea where all the money came from. Until today."

One evening, my curiosity piqued when she left her phone on the sofa to take a shower. As fate would have it, "she went for a shower, and left her phone on the sofa. Suddenly, her screen lit from a message notification."

I wasn't one to snoop, but the preview text caught my attention. It read: "Payment Received: $500." I felt a sinking feeling in my stomach. I feared the worst, but I had to know. I opened the message and what I discovered was both shocking and strangely admirable. My daughter was not involved in anything illegal or indecent, but it was still her "NASTY secret."

As it turned out, my daughter had been selling her art and design services online. She was a digital artist who was making serious money from commissions and graphic design projects. Not only was she doing what she loved, but she was also earning a considerable amount of money from it. All this while managing her college studies.

"And I must admit: it was kind of genius." It wasn't the secret I expected to find, and while I was initially upset about the secretiveness, I was also proud. Here was my daughter, an entrepreneur in her own right, finding her way in the world and making a name for herself, all at the age of 18.