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We’re all encouraged to be clever and use our critical thinking skills from a very young age. But sometimes, these skills come back to bite companies when they realize that they left gaping loopholes open that customers are happy to exploit…

Redditors have recently been recalling the most brilliant loopholes they’ve ever discovered, so we’ve gathered their best stories below. From hacks that save money to clever tricks that result in free food, enjoy reading about all of the ways people learned how to exploit the system. And feel free to take some inspiration from this post the next time you’re looking to save some cash. Just make sure to read the fine print first!

#1

30 Times People Cheated The System After Finding Insane Loopholes This was COMPLETELY unintentional but still a hilarious loophole.

I wanted to cosplay Lois Lane at a local con. I printed up a Daily Planet press badge with a picture of the actress who played Lois Lane in the Smallville TV show. I copied Lois's outfit in the Superman animated series and had a friend with me dressed as Jimmy Olson. We went around "interviewing" cosplayers as a bit which got a lot of chuckles and we met some cool folks. Some DC comics cosplayers even tracked us down to get pictures.

However, completely by accident, we walked past a panel room with a sign that said "press only". A bored staff member was by the door. When he say us, he waved us in! We were giggling but decided f**k it, let's go.

The panel room was where the con guests/celebrities were answering press questions and promoting upcoming projects before doing meet and greets and the like. We ended up spending most of the day in that room listening to Peter Dinklage, Alan Tudyk, and a bunch of other people chat about what they were currently working on. We didn't ask any questions because we didn't want to get caught but it was a lot of fun!! Would do again.

eeriedear , Immo Wegmann/unsplash Report

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    #2

    30 Times People Cheated The System After Finding Insane Loopholes My brother once yelled “last one to jump in the pool is gay,” and then jumped into the pool. However, I figured out that if I did not jump in then technically he would be the last one in the pool, and he is still gay to this day.

    Star_dustts , Katherine Auguste/unsplash Report

    #3

    30 Times People Cheated The System After Finding Insane Loopholes If you're catholic you can do anything you want and get off scot-free by going into a booth and telling a guy and then doing a couple of short chants.

    DoinIt4DaShorteez , Shalone Cason/unsplash Report

    To find out more about how this conversation started, we got in touch with Reddit user _ZoroX_, who posed the question: "What's the best loophole you've ever discovered?"

    They were kind enough to have a chat with Bored Panda and share what inspired them to start this thread. "I was just thinking about interesting topics, and this was the first thing that came to my mind," they noted.

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    But apparently, the OP doesn't have a lot of experience exploiting loopholes in their own life. "Not mentionable ones like those in the comments," they shared.

    #4

    30 Times People Cheated The System After Finding Insane Loopholes This is no longer relevant, but it saved me hundreds and probably thousands of dollars. In 1998, I bought a digital cell phone from AT&T that only had 90 minutes of talk time per month. The rep at the store told me that to save on my minutes I could forward my number to my home phone and I wouldn't be charged minutes. I asked what would happen if I forwarded to a different area code and he told me that there is still no charge. Back in the 90's, long distance was very expensive by the minute. So I discovered that I could call my girlfriend, who was an hour away and technically long distance, by just forwarding my number to her number and calling my own cell phone. There was no charge for this talk time because it was a local call for me. I would get 10 page phone bills and would show 0.00 for every single one of those calls. I was 18 years old and we spoke every day and it didn't cost me a dime.

    This-Above-All , Wesley Tingey/unsplash Report

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    #5

    30 Times People Cheated The System After Finding Insane Loopholes I didn’t find this loophole myself but my friend did: A few years back, an online store had this promotion where whoever spent the most money over a month would get free round trip airplane tickets to anywhere in the world. My friend (who’s a f*****g genius) found that one thing you could buy on the site was a gift certificate. So he bought a $25 gift certificate and kept spending it on another $25 gift certificate. So he ended up spending $25 on round trip tickets to Australia.

    Beautifull_Fairy , Ave Calvar/unsplash Report

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    TBW
    Community Member
    1 day ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Pretty much every website doesn't let you buy gift cards/certificates with another gift card. There's like a 0.0001% chance of this story being true, let alone the free trip promo also being unlikely to be true.

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    #6

    30 Times People Cheated The System After Finding Insane Loopholes 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.

    BananaasDirty , Andy Quezada/unsplash Report

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    Toothless Feline
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    There are a lot of weird scholarships and grants that go unawarded in many years because people who are eligible don’t know they exist. It pays to do deep research on scholarships.

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    We also asked the author if they think it's right for people to be exploiting loopholes. "If it's not straight up stealing, just exploiting a 'bug', then yes," the OP says.

    Next, we asked ZoroX what they thought of the replies to their post. "There were pretty interesting ones, however, some of them were just straight up lying and stealing," they pointed out. "Like the ones saying that their items didn't arrive when it did, etc... They are not even loopholes, they are just lying and being dishonest."

    #7

    30 Times People Cheated The System After Finding Insane Loopholes My high school had a stupid rule that banned you from attending prom if you went to a saturday detention that semester. I got in trouble and was assigned to Sat. D-Hall, 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.

    Mermaid_sapphire , Tai's Captures/unsplash Report

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    #8

    30 Times People Cheated The System After Finding Insane Loopholes Figuring out that if you bring a clipboard and walk with purpose, almost nobody questions why you're there.

    Banes_World_Archive , Centre for Ageing Better/unsplash Report

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    #9

    30 Times People Cheated The System After Finding Insane Loopholes Arby's had a promo where if you signed up for their email address, they gave you a coupon for a free main (no purchase required.)

    So I showed the cashier the coupon on my phone and they just plugged it in. No unique code or anything.

    It expired in 3 months so every day at work I got a free sandwich. And on the last day the cashier said "oh we honor expired coupons"

    And that's how I got completely sick of Arby's.

    darkperl , Ben Schumin/flickr Report

    Finally, the author added that, in their opinion, "the biggest loophole glitch discovered ever" was when Australian bartender Dan Saunders found an ATM glitch in 2011 and ended up spending $1.6 million of the bank's money. That's a pretty big glitch!

    #10

    30 Times People Cheated The System After Finding Insane Loopholes Discovered that my high school P.E. teacher graded on improvement. You took a skills test at the beginning of each unit, then one at the end of the unit and your grade was based on how much you improved. I was not the most gifted athletically, always got C's in P.e. before this, so I would tank the opening test, then perform my usual mediocrity at the end, but my improvement was awesome and I became an A student the last semester of high school P.E.

    LordBaranof , Victor Freitas/unsplash Report

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    Forrest Hobbs
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Actually, that sounds like a PE teacher trying to do a decent job in a decent way. None of the sadism I've heard about from some. I had a PE teacher who had been an old-time military PT instructor before he went to teach in schools. He was exceptionally kind and decent and had absolutely no time for bullying or mockery of the less able kids. Oh, you think that boy is silly because he can't do pull ups? He'd then demonstrate doing pull-ups with one arm, looking at the source of the bullying. That kind of thing. Very good bloke.

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    #11

    30 Times People Cheated The System After Finding Insane Loopholes 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 was two part, which is two sheets of paper that are attached together back-to-back with a sheet of carbon paper in between. I could peel the sheets apart and look inside: the second sheet just had a bunch of boxes printed on it, and I could see from the first few questions that I’d answered that the Xs I’d marked ended up in the printed boxes on the second sheet thanks to the carbon paper.

    So, I did all of the questions with obvious answers, and if I was unsure, I just peeled the paper apart, noted where the box was printed 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.

    Breezyy_Roses , Nguyen Dang Hoang Nhu/unsplash Report

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    #12

    30 Times People Cheated The System After Finding Insane Loopholes In one town I lived in parking tickets were cheaper than paying for parking, cost nothing against your license, and the area I parked in had a satellite office right where I parked where I could pay the ticket right away. It wasn’t even that common to get a ticket.

    Gal_GaDont , Caspar Rae/unsplash Report

    #13

    30 Times People Cheated The System After Finding Insane Loopholes I found these neat things on my pants that keep my belt attached to my pants.

    BeardsuptheWazoo , Siep van Groningen/unsplash Report

    #14

    30 Times People Cheated The System After Finding Insane Loopholes I work at a well known Australian alcohol store, up until very recently the online store would mark down slabs (24 bottles/cans) of several different craft beers from $60-$70 down to $24. This would only happen if you put 24 individual cans or bottles into your cart instead of a slab. This guy would click and collect 24 individual bottles every week.

    Obviously the staff I worked with weren’t going to unbox a slab into 24 individual bottles so we just gave him a slab.

    Management told corporate about this several times over years but they did nothing until one day the man came in and said they had closed the loophole, however he was still able to just click re-order and got the same price that he had already been paying.

    The company makes billions in profits each year, so more power to him!

    Tldr: infinite $24 slabs of craft beer.

    Karma_Koala85 , Kyle Wagner/unsplash Report

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    #15

    30 Times People Cheated The System After Finding Insane Loopholes The local radio always have a contest where you call when they play same artist back to back so you can win a prize. Then I learned they had a "now playing" and "up next" feature on their web site. My girlfriend that time would start calling in before second song even came on. Won a ton prizes including laptops.

    Babyygirlly , Andrej Lišakov/unsplash Report

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    Matthew Currie
    Community Member
    20 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I don't think this works any more, but way back in the 1950's my parents listened to a radio quiz show, and realized that if you dialed all but the last digit of their number, you'd be the first to answer. As I recall, the main prizes were products from a business called "Virginia Dare," food and the like. But once, trying to fund a foster child's visit to the US for prosthetic surgery, they won something like a thousand dollars. The kid (a Greek child whose hand had been blown off by German mines) got to visit the US, and with added help from the VFW, he got a prosthetic hand. It got a nice writeup in the papers, but needless to say it never mentioned they'd cheated on a quiz to do it.

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    #16

    30 Times People Cheated The System After Finding Insane Loopholes Not mine but many years ago a woman was attending college in Texas and paying out of state tuition. She found out that if you were a business owner in the state you could get in state tuition. She spent a few bucks to file for a business and saved gobs.

    hotbutteredtoast , Element5 Digital/unsplash Report

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    Owen
    Community Member
    23 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    All Americans should become incorporated at birth. It's the only way to win in this system - be a business.

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    #17

    30 Times People Cheated The System After Finding Insane Loopholes Parking at the hospital the pay machine wasn't working so I drove to the barrier and pressed the button to speak to the attendant / security... A few seconds later, without a word being exchanged in either direction, the barrier opened.

    This was early on in my dad's hospital stay of about 9 months.

    I didn't try paying again, just pressed the button at the exit barrier...

    TechStumbler , Mauro Sbicego/unsplash Report

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    MalayDragon
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Being made to pay for parking at a hospital is in my opinion disgraceful and disgusting. The last thing families of people who are in hospital for any reason should have to worry about is how much they're going to have to pay for visiting their loved ones.

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    #18

    30 Times People Cheated The System After Finding Insane Loopholes In university I didn’t have my own printer. Had to swipe my student ID to pay to print anything on the library’s printer. Charged something like 10 cents per page. I would go and select the document name off of the touch screen, then swipe my card and it would print as well as charge me account. I discovered that if I gave my document a really long name, the computer didn’t know what to so with it. So instead of going to the queue it just bypassed the pay screen entirely and printed.

    Pilotx15 , Getty Images/unsplash Report

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    Mr. Sourcrowd 🧐
    Community Member
    16 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Did you discover this by printing the ›Title of Thesis final final this time really final final absolutely final dhdj 28.pdf‹?

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    #19

    30 Times People Cheated The System After Finding Insane Loopholes There was a drink machine in college that was $.75 for a juice. If you put a dollar in it gave you 5 quarters in change. I got a juice everyday for months before they finally fixed it.

    Dreammy_Glitter , Agustin Farias/unsplash Report

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    Nice Beast Ludo
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I found a machine like that at the Public pool. I put a dollar in but didn't have the extra quarter so hit the return button and got like $8 in quarters. I was going to do it again but then I felt bad for whoever owned the vending machine so I didn't. I just bought a shitload of snacks.

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    #20

    30 Times People Cheated The System After Finding Insane Loopholes I’m not sure if they do this anymore, but many years ago, while an employee at HomeGoods, the store had this promotion where, employees could get these scratch-off cards that reduced the cost of an item by 1/5/20 dollars each time they found a price sticker on the floor. Each card had three scratch-off areas, and the catch was that you could only scratch off one.

    However, if you used a lamp, you could see which scratch off area was the 1/5/20 - meaning that you could very easily rack up a 20 dollar gift card for every sticker you found on the floor.

    The idea was that if employees collected these fallen stickers, regular, nefarious shoppers, couldnt stick them on something of far greater value and check out at that price.

    There were no rules on how many an employee could have, or combine, because most folks who worked at that store were middle aged women who really couldn’t give a f**k and most of the stuff HomeGoods sells is garbage.

    But then there was me - a starving, broke college kid, who got paid s**t, but who worked in the back room unloading trucks, and who also was occasionally tasked with stocking shelves. In short, I was the only person who seemed to give a s**t about this promotion, and my bosses, who wanted to show their higher-ups that they were putting the corporate programs into effect, were happy to oblige each sticker I presented with a scratch off ticket of my own.

    Now HomeGoods, while normally a purveyor of fine garbage, also occasionally has very nice, very high end, house-wears on the cheap (comparatively), these items, like cook-wear, linens, comforters, etc, are more often than not, usually much more expensive than the rest of the store’s stock, and take a while to sell.

    For me, the guy who unloaded the trucks, this meant that when I saw something absurdly nice, I could put it very high up into a loading bay, and just let it sit for a while, because the senior citizens I worked with would never go up to get it.

    At the end of a 4 month summer, I’d amassed about 1100 in these little gift cards, and with them I bought:

    A full set of AllClad copper core cookwear (a new piece came in once a month)

    A Queen sized down comforter, duvet cover and sheets

    Pillows

    Nice flatware, Plates and Glasses

    A dozen useful kitchen tools

    To this day, ten years later, I still have all the AllClad, which alone retail for 800, and some of the kitchen tools.

    All of it for free.

    Siren_beauty , JJBers/flickr Report

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    #21

    30 Times People Cheated The System After Finding Insane Loopholes 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.

    Gigglyy_Queen , bobbsled/flickr Report

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    Parmeisan
    Community Member
    1 day ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Ooh, image courtesy of Canada! The other side will be in English. (Edited to add, I know there might be other places in the world that use French and also use dollars, but the clincher is the .ca website.)

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    #22

    30 Times People Cheated The System After Finding Insane Loopholes I live in a remote, rural area. We don’t get UPS packages delivered on Tuesdays or Thursdays. When I order Amazon, it gives me the option to choose Friday delivery with a $1-$2 coupon for digital orders. I always choose that option bc I’m not getting a Tuesday/Thursday delivery anyway. So I stack the coupons and get a bunch of kindle books for free.

    bluegenes71 , Super Straho/unsplash Report

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    #23

    30 Times People Cheated The System After Finding Insane Loopholes I had two loopholes that I routinely exploit at work (and I recommend it to my employees, though none have the discipline). It lets me take 1 month of vacation each year, instead of just 2 weeks.

    Loophole 1: All OT will be matched with PTO/Paid Vacation time.

    Loophole 2: Clocking in 5 minutes early and Clocking out 5 minutes late will count as OT, but not require manager approval.

    By Clocking in 5 minutes early to start my shift, out 5 minutes late for lunch, 5-early to come back from lunch, and out 5-late at end of shift, I got 20 minutes of paid OT and 20 minutes of Vacation time each day I worked.

    Each year, we get 80 hours of PTO, but with my scheme, I get an extra 83 hours and 20 minutes. And that's not counting any extra PTO I received when asked to work overtime.

    WatchingInSilence , Getty Images/unsplash Report

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    Verena
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Why is this a loophole? OP is at work during that daily 20 extra minutes, so no actual "win". However, I am satisfied with my 25 days of holiday (which is lo)w for European standards and indefinite sick leave, if a medical insitution confirms I am actually too sick to work.

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    #24

    30 Times People Cheated The System After Finding Insane Loopholes A few years ago before I could drive, I used to get the bus to work. I would spend about £80 a 4 week on a bus pass each month

    On the app on my phone when I would buy the pass, it would stay on the app unused until I clicked the button then it would start counting down 4 weeks.

    I figured out if I buy a 4 week ticket and back up my phone whilst it’s unused I could then reinstall the backup after a month and have a new unused 4 week ticket

    I did this for about 3yrs and saved nearly £3000, I’m still happy about this.

    TheMarvellousMrMaz , Getty Images/unsplash Report

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    Fellfromthemoon
    Community Member
    22 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    In my country, many found a loophole: they simply don't buy bus tickets and run when (occasssionally) meet an inspector./s

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    #25

    30 Times People Cheated The System After Finding Insane Loopholes They cottoned on pretty quickly but a few years back, I managed to purchase some buy-one-get-one-free meals from Tesco that were also yellow stickered. The system hadn’t been updated to remove the offer, which meant I ended up effectively being paid to take the food home. For example, I bought two ready meals that were originally priced at £2 each. Normally, they would have cost £2 total with the BOGOF offer, but since they were further reduced to something like 40p each, the full promotion still applied. When I scanned them, the total came to 80p, but the system also refunded me £2.

    peanutbudderlover , seefroo/reddit Report

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    Ace
    Community Member
    1 day ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Yeah I've had similar things like that a few time over the years, in the UK and France. For non-Brits, the 'yellow sticker' is a reduced price usually due to a close best-before date, and BOGOF stands for Buy One Get One Free.

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    #26

    30 Times People Cheated The System After Finding Insane Loopholes In college the local Buffalo Wild Wings would give out like 6 free wings if you did their online survey. I found out they didn't really put a limit on how many times you could do it and I just so happened to work during the time that the cafeteria was open for Sunday dinner.

    I had Buffalo Wild Wings damn near every Sunday because I would get six free Wings and something else. I was severely disappointed when I came back next year and the deal was gone.

    AnAngryPirate , Davey Gravy/unsplash Report

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    Geoffrey Scott
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    We signed up as 'mystery customers' for a national pizza chain. Would send a coupon worth a free small pizza every time you graded the service and quality. Did that for a year, until they tightened the delivery area. Free pie every month.

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    #27

    30 Times People Cheated The System After Finding Insane Loopholes 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.

    BlusshFoxx , Geonhee Lee/unsplash Report

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    #28

    30 Times People Cheated The System After Finding Insane Loopholes Bought a pie from supermarket, box came with a token for one free pie.

    So... bought a pie, went through checkout, removed token from box, went back got another pie, paid with token, and went around again. Filled freezee with pies.

    DrunkStoleATank , Curated Lifestyle/unsplash Report

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    Nice Beast Ludo
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    You are the reason why you have to wait 24 hours to cash in on most promotions like theses

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    #29

    30 Times People Cheated The System After Finding Insane Loopholes My brother found out that at some point McDonald’s were giving a Big Mac if you bought a 50$ gift card. The thing is that you could buy a 50$ gift card with a 50$ gift card. Needless to say that he got a couple of free burgers during that promotion 😅.

    LeditGabil , Annie Spratt/unsplash Report

    #30

    30 Times People Cheated The System After Finding Insane Loopholes Using a free trial with a new email every month to avoid paying for a subscription.

    Omnibusnew , Getty Images/unsplash Report

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    ChugChug
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Until you forget about that and they start charging you, and you end up forgetting to cancel it month after month, and finally a year later you get your lazy bum on front of the screen cancel it. And you feel epic but disappointed the same time about how much money you have wasted. Happened to me :(

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    Note: this post originally had 76 images. It’s been shortened to the top 30 images based on user votes.

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