40 Times People Online Discovered Loopholes And Proceeded To Abuse Them Beyond Belief

Loopholes are… interesting, to say the least. There’s the obvious gain more for less deal or gain something when you should’ve gotten nothing, but there’s also the excitement of finding the loophole and seeing it work. Some are more obvious than others (both in terms of discovering the loophole and someone figuring out that you’ve done it in the first place), but it’s exciting nonetheless.

And folks on Reddit were sharing this excitement in a recent AskReddit thread, where they answered the question what loophole did you exploit before someone found out?

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My old apartment complex had a soda vending machine at the pool that was broken. If you put in 50 cents and pressed the button, nothing happened. If you put in another 50 cents and pressed the button, nothing happened. But if you put 50 cents in a 3rd time and pressed the button, you’d get 3 sodas. I could see the vending machine from my couch. So I would watch for someone to try, and then try again, and then give up without trying a 3rd time. And then I’d head over and get 3 sodas for 50 cents. .

Image credits: bacchus8408


Back when physical media video rentals were still a thing, we were gifted a Blockbuster gift card for a free rental. The card proved to be unbreakable. Everytime we rented a movie I would hand the clerk the card. They would scan the bar code on the card, hand the card back, and the movie was free. We used the card for about 3 years until our local Blockbuster closed. There was obviously some sort of software error, but the gift card was never rejected.

Image credits: sretep66


A new Fast Food place opened near my work. My mother-in-law got me a gift card to the place as a birthday gift. I went on opening day and tried to use my gift card, they said the system wasn’t in place yet and just gave me my food for free. This worked for almost a month. It was the best gift card I ever had! Started with $20 on it and I got at least $100 worth of food.

Image credits: Ackmiral_Adbar

For context, loopholes are, in essence, workarounds in a system or structure that benefit someone when it wasn’t necessarily possible. At the very least, it wasn’t intentional in the beginning, but somehow nobody either noticed, or nobody ever bothered to do anything about it. And, so, here we are, with people getting away with something without anybody technically being able to do anything about it.


When my baby was in the NICU for two weeks after birth, I realised if I waited for about 30 seconds, the hospital car park barrier would just open without me having paid. Saved a lot of money.

Image credits: crimp_dad


For a while, you could buy $1 coins from the US Treasury using credit cards. They would ship them to you for free.

If you had a rewards credit card, let’s say an airline one, you could buy thousands of dollars of coins. Go to a bank, deposit them, and then pay your credit card back.

It was a good way to get a ton of points for flying without ever paying for anything.

They stopped doing this.

Image credits: defroach84


I used to work for Sears as a teen. When someone came in without the rewards program, I would just put my own info in. That way my sales percentage for rewards members didn’t drop, and I got all of their points. The amount of coupons and free money was insane, especially when I was working back in the tools department. I didn’t stop until they started upgrading their ancient point-of-sale system. I also had an employee discount of 20% on softlines (clothes, home, etc) and 10% on hardlines (tools), which they didn’t take away for a few years after I quit.

Image credits: sasspancakes

Now, is it a bad thing? Well, for the person gaining something from it, it most certainly is beneficial and hence good. Unethical and immoral? Absolutely. But is it legal?

Loopholes are considered a particular kind of gray area where legality is often not an issue, but it does stir quite a bit of trouble because anybody with a voice can start calling you out for exploiting the system.

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Had a college professor that insisted on doing all tests and quizzes online. If you looked at the page through ‘View Page Source’ all of the answers for each multiple answer question had a marker on which one was correct.

Image credits: bunnygang


Buffalo Wild Wings used to have a check-in thing. Check in enough times and you get a free meal. The office I worked in was close enough, geographically, that I could check in from there without physically going to the restaurant. A bunch of coworkers and I had an alarm to check in every day and then once we all had the free meal, we’d go there for lunch. I got probably 4 or 5 free meals out of it before BWW revamped that system.

Image credits: totallyarealusername


When in highschool there was a company that offered money to run an advertising window at the top of your screen. It would monitor mouse movement to track whether you were at your computer and pay a small amount per hour.

A buddy and I downloaded it and a mouse moving software and would run both 24/7, except when we were on the computer. Made a few hundred dollars off of it before the company closed down.

Image credits: Aken42

But if it’s technically legal, why does it make it unethical and immoral? You see, loopholes can be evil, for a lack of a better word. And there are varying degrees of it. It depends on how you look at it. But generally speaking exploiting a system deliberately is not something most would consider fair and thus not good, especially if it’s at someone else’s expense.


I learned before my ASAF basic training to say that I played an instrument whenever they ask the group on the first day. I raised my hand and lied, “the cymbals.”

So most days I got to angrily smash cymbals together in the air conditioned band trailer, instead of marching/drill practice in the San Antonio summertime sun.

Image credits: HuuffingLavender


Found a website where you had to vote for best diving liveaboard company.

It was shared by a company in the competition trying to boost the votes. The first prize was a dive trip in the Maldives for 1 week on their liveaboard.
I found a flaw in the voting system and asked the company trying to win if they counted individual votes as entries or 1 person gets 1 vote. They replied that each vote counted as an entry.
Politely told them to prepare me as the winner.
The flaw in the website was that it used simple cookies to check if someone has already voted.
Made a script to vote and clear cookies – rinse and repeat.

I had a great trip scuba diving for a week in the Maldives!

Image credits: does-this-smell-off


When I was in middle school, Pepsi did a thing where if you bought a 20oz soda, there was a decent chance the cap would say you were a winner on the inside, and you could exchange it for another 20oz.

Problem is, a dark colored soda like Pepsi is reflective. Hold the bottle slightly tilted and you could look at the reflection of the inside of the cap.

For a whole school year I didn’t pay for soda. Bought a winner, and every day I’d exchange the cap at a gas station I passed on the way home for another winner.

Eventually Pepsi caught on and instead of it saying you won on the cap itself, there would be a code you had to enter online. We didn’t have the internet in our pocket in those days (and it wouldn’t have been worth it to read and enter multiple backwards codes for a soda if we had) so this ended the scheme.

Image credits: LupinThe8th

You can argue that looking for loopholes is natural for humans. Mainly it’s because some suffer from severe laziness and, like electricity, they look for the shortest path possible to success. And then there’s also the desire to get free stuff, even if it means compromising your moral reputation.


For a year I lived in a house in London that was split into three flats. The landlord had submitted meter readings before I moved in, so I just waited for each new bill to put my name on the accounts.

When we moved out, I went to submit the meter readings and couldn’t figure out who was supplying our gas (heating and cooking). Couldn’t find any bills, couldn’t see any payments from my bank accounts, it was a mystery. Ended up just calling suppliers asking if they had an account for my address.

In the end it turned out that whilst three meters had been installed for the flats, only two had ever been registered. Without a contract with a supplier (or even any readings for the years the flat had been there), there was no way we could be charged for our year’s usage – or for the few weeks until we moved out whilst a new account was set up. As the guy from the gas company said to me “Congratulations – you have free gas!”

The annoying thing was that we’d kept the thermostat down during the winter to save money. Went totally wild for those last few weeks though.

Image credits: prolixia


Work allowed us to skip breaks and bank them, but the contract language basically made it so you could bank both 15 min breaks each day, as well as bank your lunch if you never technically clocked out. So I’d just eat while driving from job to job, and bank an hour a day.

Was able to use all that time after a while to take an entire month off of work, paid, without even using any of my assigned PTO. HR got pissy about it and tried to rake me over the coals when I got back, but I pointed out the contract language and they realized their hands were tied.

They pushed out a new contract to fix this exploit, but my work contract was still good for another year, so I declined and kept banking time, taking time off when I wanted. Of course they didn’t offer me a new contract once mine was up, but I had a better paying job closer to home lined up already anyway, and took the last 2 months off, paid, while I started my new job, so I was basically getting 2 salaries.

Image credits: InfernoWoodworks


Coca Cola did a campaign where you registrer a code from the bottle cap and earn prizes. I worked at a store with bottle deposit and “earned” myself a sweet mp3 player with room for 5 songs or something. I was the only one I knew that had a mp3 player, so it was pretty sweet at the time.

Image credits: aftenbladet

Then there’s also more justifiable (sometimes) reasons to abuse loopholes, and that is to fix an existing system by proving a point. In other words, you use the system and then someone gets so upset with you that they make it right. Win-win?

Or it’s the other way around—the existing system is unfair to you, and so you abuse it to make it fair—like ripping a CD for your personal convenience.


Back in the late 90’s with the dot com boom there was a web site called Prize Point. You would play one of their many games, when the game was over you would hit a cash out button and win tickets that was based on your score. My computer was running slow with dial up internet and I was frustrated and hit the cash out button a whole bunch of times. The next thing that popped up was I reached my daily limit of point, something I had never done before. I started doing this everyday and reached the daily limit with just 1 game. The tickets were used like raffle entries for one of their prizes, 1 ticket= 1 entry. I saved all of mine for months and dumped them into a trip to Hawaii. It was one of my best vacations ever.

Image credits: Tasty-Run8895


I once got a CatDog piggybank by clicking their online game’s “next” button repeatedly for more points. It was the second prize, but it was the neatest thing ever.

Image credits: DreyfusBlue


Not intentionally, but I discovered after the fact that a $29 bottle of local wine at the market wasn’t on clearance for $6, it was a mistake in the system. It was really good and I probably bought 6 bottles or so over three-ish weeks. .

Image credits: audiate

Loopholes also trigger a sense of achievement and boosts our intellectual ego because we had to be clever enough to find it. Or anarchistic enough to go against being told now. Whatever the case, does it make it wrong or right when the system allows for it? Again, it depends.


Taco Bell had a $5 box deal to win a PS4 before it was released to the public. I found that towards the end of the promotion you could enter to win without purchasing a $5 box. You could only enter once per pone number and address… Also the rewards were time based, every 15 minutes someone would win. I woke up every night at 3:16 am and entered 4 times, using my home, work, and my Mother in Laws home and work numbers and addresses. After about a week I was about to stop AND I WON!!!! I had a PS4 3 days before the public could even buy them.

The next year I did the same thing and won a second PS4 for the kids game room.

After that they changed the rules slightly to make it much harder to game the system.

Image credits: stratospaly


Microsoft back in the day had a marketplace that used Microsoft points. You could buy games, xbox controllers, xboxes etc but it was a marketing program that just wanted you to use bing instead of google.

I can’t remember most games but I know there was a game called chicktanary or something like that and me being a little turd who liked computers, I found a bot that played the game for me.

I got so much free s**t from that. lol



McDonald’s app uses to give out free ice coffee with 1 dollar purchase. After doing this daily they finally nerfed it to 5 dollar purchase for free ice coffee.

Image credits: Fuzilumpkinz

So, where do we draw the line? No matter how you look at it, exploiting a loophole does pose a non-zero chance of facing consequences. Direct or indirect.

First, and foremost, ask yourself whether abusing this particular loophole is breaking the law? If it is, better not do it. If it isn’t, then proceed at your own risk, but at a lesser risk. But still at risk.


I used to buy the teacher’s edition of textbooks. Tests and quizzes in the back. Lazy teachers never changed a thing. Nobody ever found out.

Image credits: Peterthinking


No one ever found out, but they didn’t know how to set up Unix when I was in college. You could drop to the parent directory in programming classes, and go into the other classmates folders see how they were coding their projects. Just in case you couldn’t figure out a section of your code…

Image credits: Blow1nginthewind


I went to high school in the late 90s, when the internet was basically the wild west. Certain terms and domains were blocked on the school computers, but you could navigate to some pretty shady sites by simply following links.

We had a game where we’d start on disney dot com and click links and see who could get to the “worst” site. It was a mildly amusing way to waste time during class.

Next up, ask yourself is it affecting someone else? If not you, then someone else might get into trouble over this, and your benefit might mean imposing a disadvantage on someone else.

And if you’re thinking about that, also consider if it’s worth it. Does the benefit outweigh the risk of, say, losing a job or getting a fine?


Not me, but my roommate in college. Whenever you paid for anything on the university’s website you’d earn “college bucks”. Each year’s tuition paid for something small like a beer coozy, fold up lawn chair, or if you somehow spent an absurd amount, an official school-branded kayak.
Well my buddy found out that the points were added to your account BEFORE payment went through on the website. So he just refreshed the page over and over and got millions of points. I only found out his scheme when I came home to an entire living room filled with boxes from our school! There were shirts, coolers, chairs, cups, and of course the kayak. We opened all of it (like idiots) and had a giant laugh at the school’s expense. All of the guys living in that house were having a great time until we opened the smallest box which had 1000 $100 Visa gift cards. Then we got scared. A bunch of school-branded c**p from a warehouse was probably unusual, but not something that would bother the person loading all that up for delivery. The gift cards though? That was where he got caught. The gift card issuer called the school to verify such a large amount before activating the cards and THAT raised a lot of red flags in the accounting department. They traced it all back to my roommate and came and took everything back (they left the opened items and the worthless gift cards) and suspended him during his final semester of college. He had to write an apology letter and do community service for the school for that whole semester in return for not pressing charges for fraud. It makes for a great story though, and we had a ton of beer coozies and gift cards that we threw at each other like ninja stars.

Image credits: chincolovesyou


My college had a “points” based meal plan. 100 “points” equaled approx. $6.50. We used special credit card swipers that were able to swipe our IDs when using these points.

Midway through my first year, they decided to install self serve kiosks that could give you cash back. If you swiped your card as if you were going to pay, asked for cash back on the kiosk, and then canceled the transaction on the special swiper before it went through on the main kiosk, it would give you cash without deducting the points. So basically free money.

As far as I could tell, nobody found out I was doing it because I never saw any point deductions from my ID card and nobody ever talked to me about it. I made about $300 for free. They disabled the cash back option after a couple weeks though.

Edit: I should add, this was before tap-to-pay or EMV chips. The whole system was obviously very shoddily put together.

Image credits: irrelevanttrumpeter


Was told in my first day on the job at six flags that our till could be $25 off each day without anyone noticing or caring.

Image credits: klitchell

Lastly, consider your personal reputation. Sure, you might not care and can take a hit, but if you’re a big deal in your area, would that set a good example?

Rules, no matter the system, shouldn’t be broken, but loopholes soften the blow, in some ways, and if nobody is there to see you do it, it might just be a mystery of how this one machine seems to be dishing out 3 cans of soda at once.


About 25 years ago Microsoft had a training program where you would take tests for points depending on your grade. You could use those points for free stuff. The loophole was that if you answered a question wrong, you’d lose your points and it would tell you the correct answer, so you could press the back button, fix your answer, and resubmit. I had gotten myself a bunch of shirts and hats, and even managed to get an ink jet printer before they caught on.

Image credits: TehGroff


I’m a traveling RN and on one particular assignment the cafeteria staff was under the impression that travel nurses ate for free. Anything we wanted and as much as we wanted. So for almost 6 months I got all of my meals for free and I also picked up extra stuff for my friends on the unit. Eventually they sent out a hospital wide email stating that we absolutely do not eat for free and never was supposed to get free food so that ended that.

Image credits: Ok_Button1932


Parking spot in the corner of my college dorm lot. It wasn’t a spot as it had a parking curb placed in its location (like, parallel in the middle of the spot, not marking the end of the spot where the front wheels would bump). My car sat high enough that I parked there for a good year before I got my wheel booted. Still saved $1500.

So, what are some loopholes that you’ve abused in your life? Or wish that you have? Share your stories in the comment section below!

And if you haven’t yet, then you can continue scrolling through more loophole inspiration.


Up until mid-2023, in the Subway app you could type 599footlong in the coupon code section and any footlong would be $5.99. Then one day everything changed. .


Shell airmiles coupons.

99% of the people in my local shell station didnt care about collecting them. The cashier would tear them out (they came in a coupon book) and they would be stacked to one side and given to whoever asked for them.

I had a company car at the time and stopped in quite regularly. I asked for them. I got a whole load of them before shell stopped the promotion.


Company I worked for had an employee benefit called a “Lifestyle Account” basically it was a $500 per year reimbursement allowance that could be used on anything related to health/fitness/personal enrichment. The company was very flexible with the rules and you could get away with buying all kinds of things with it. The money would not roll over to the next year if you didn’t use it though.

Every year I would buy myself an Apple watch for $500, screencap the receipt, cancel the order and then collect the $500 reimbursement.

Image credits: pofwiwice


I received thousands of dollars of stock certificates in the mail. Some intern f****d up so badly that my broker said to hold on to it. I held the stock for years before selling it at a profit.


I bought something from Dollar Shave Club once, my order came and I thought that was the end of that. But 2 months later I got another package from Dollar Shave Club filled with stuff, razors blades, handles, shave butter, face wash etc. I checked all my credit cards and had no new charges from DSC. I kept all the stuff they sent and moved in with my life 2 months after that I got another package of razor blades from DSC.

One day I was looking though an alt email account and found some emails from DSC alerting me to update payment information and shipping confirmation. Turns out I had made another DSC account prior but for some reason someone else’s order and credit card information was linked to my account. Their CC# was no longer valid and this is where the loophole begins.

Every month DSC would try to process a subscription order for razor blades. It would fail because the CC# on the account wasn’t valid, but the month after that it would complete the order, maybe because there was an order from the previous month that wasn’t fulfilled. So every other month I would get razor blades from DSC. I started adding a bunch of stuff like hair gel, face wash, etc. This went on for 2 years before they realize.

Image credits: n80r


Coming in to senior year in High School, a couple dozen of us were competing for the top 1% for GPA. Honors classes were on a 5.0 scale instead of a 4.0, so gave a big bump to your average. Very few electives were honors, mostly just core classes. One of my friends noticed that there was a Math 1/2 honors class that none of us took – we all took it in middle school and went straight into Math 3/4. We looked up the policy and nothing said you couldn’t go back and take a lower level class, so 3 of us signed up for the honors Math 1/2 course with freshman. The teacher sat us in the back. I worked on calculus or physics homework or played Minecraft on my phone. Teacher completely ignored us.

Half a dozen people did it the next year. The year following when by younger brother and his friends tried to do it, they changed the policy.


Free sandwiches from CFA based on location. Used gps spoofer and got tons of free sandwiches a week on multiple accts. I think I got about $5000 worth of sandwiches and nuggets before they banned me.

Image credits: NegMech


My uncle lived in Thailand.

Before the Euro the 1 Baht coin was a perfect match for the 50 Pfennig coin. I lived in Frankfurt. Several Parking places close to my work stopped accepting 50 Pfennig coins (And then the € came).


Arcade tickets go into counting machine, machine print receipt with number of tickets entered. Could do what we came to call “ticket wanking”, pulling the same line of tickets in and out real fast to get number up without losing tickets. Could also just shove cardboard in, too many kids did that and machine was changed.


I was doing genealogical research of my Scottish roots. The Scottish government website uses a “credit” system. 3 credits for this 5 credits for that.

There was a travel website that would give you a code for 10 free credits for signing up for their email newsletter.

I used an anonymous email service to generate one time use email addresses over and over to get unique codes for free credits. This allowed me to load up on credits, and go back a couple hundred years…

Eventually they took it down due to “inappropriate use” – likely when thousands of their monthly newsletters started bouncing back from “mailinator”.
Source: boredpanda.com

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