Brilliant Loopholes People Exploited For Years

Author image for Mel Dawn
Mel Dawn
Feb 19, 2022 8:00 PM EST

We always love to see ordinary people exploiting glitches in this messed up system, flawed discount deals, lazy employers, and any big institution that profits from usually doing the exploiting. When you spend most of your life rising and grinding every damn day to pay the bills, even the smallest win can feel like striking gold, like figuring out how to secure a free weekly lunch for the next couple years. 

We've got a bunch of great examples of clever people taking advantage of loopholes thanks to a hot recent thread from r/AskReddit. Maybe you'll learn something.

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  • 01
    Text - r/AskReddit u/SterlingBoardman · 1d Top Awarded 1 1 1 1 97 2 137 O 74 3 97 E 68 What loophole did you exploit for years before someone found out? 64.1k 16.3k 1 Share
    via r/AskReddit
  • 02
    Text - Johnsendall • 1d O 15 Awards I paid three hundred dollars a month to park a really pimped out van in a heated garage in Boston. If you parked front in no one could see you. Found a spot near an electrical outlet and ran a line into the van. Paid for a $10 gym across the street that was open for 24 hours so I had all the hot showers I wanted. Served at a nearby restaurant so ate most of my meals for free. Watched tv on my laptop with the free WiFi from the coffee shop above me. Literally l
    via r/AskReddit
  • 03
    Text - SpookyPlankton · 1d 3 1 Award There is an app for a local burger chain where it allows you to "roll the dice" to get a code for a free double-patty burger upgrade. It was designed so you could only try it once per day and it even shows the date of the roll on the code so the cashier could verify it. However, I found out that you can just change the date on your phone and try again immediately. If you got nothing, change it again and just keep going until you get the code. Then, when you g
    via r/AskReddit
  • 04
    Text - btpn-425 · 1d S 15 Awards When I was a kid there was a pay phone down the street that if you put your quarter in made a call but no one answered it would give you back two quarters. Went there all the time and called home when I knew no one was there to answer. Reply 21.0k
    via r/AskReddit
  • 05
    Text - thebollard • 1d My friend used to restock condom machines in pubs and collect the money from them. The machines would always break and get jammed all the time but because it was condoms no one would ever tell someone that the machine ate their money. He would just count how many condoms were gone and give that amount of money to the company and pocket the rest. Edit: I meant to also say he moved onto another job. Apparently the next person that did it collected all the money correctly and
    via r/AskReddit
  • 06
    Text - otternoses • 1d 7 Awards I went to a sporting goods store and they asked me for my phone number when I was paying. I was in a bad mood and didn't want to fight with the clerk so told them our local area code + 555-1212 (which is the old number for directory assistance), clerk accepted it and I left. When I checked my receipt I had a huge number of loyalty points - because apparently a ton of other people did the same thing. I called the office the next day and switched the "account" to my
    via r/AskReddit
  • 07
    Text - pierrekrahn • 1d S 9 Awards parking meters took credit cards. But they weren't actually connected to a live network at all times. The machine just confirmed the card number was valid and was not expired, then spit out a valid pass. So when my card number got stolen and replaced, I kept my old, cancelled card. Of course when the system tried to run the card later it would be declined. My car and I were long gone by then. Sadly they wised up and now it charges your card before giving you a
    via r/AskReddit
  • 08
    Text - mammoth200 • 1d 3 8 7 Awards Worked out how to get the jackpot every time on a Connect 4 fruit machine in a pub I used to drink in. It would cost about £5-£10 before you'd get into the bonus round, then when you did, you'd play a connect 4 game against the machine. You place the first counter, and then after the machine places the next counter, you mirror the machines move. Every game ends in a draw, and you win the jackpot, which was £50. The pub landlord removed the machine after around
    via r/AskReddit
  • 09
    Text - Shooterdude34 · 1d S 4 Awards My old job i worked at a pretty large gym (gold level, like the 3rd highest level). Monthly fee was $79 for the gold membership but employees got a free diamond membership. Worked there for a year and a half before i quit, but my account was never deactivated. Been going there for a while completely free, still not found out. Diamond membership is like $200 a month Reply 11.4k ...
    via r/AskReddit
  • 10
    Text - Art_Vandelay_ • 1d 3 Awards Back in 1999/2000 there was this web advertising company called AllAdvantage. You could install their ad banner on your computer and it would occupy like the bottom 15% of your screen and show you ads and AA would pay you for the time you were exposed to the ads. Of course they had basic measures in place like stopping your accumulated time if your screensaver came on or your computer went to sleep. But all it took was a simple program that would keep your mous
    via r/AskReddit
  • 11
    Text - rob_matt • 1d O O 5 Awards Fun fact: AllAdvantage used Zipcodes to check you were an American citizen (they asked your name and zip code to have an account) and they were amazed because their most popular neighborhood was an incredibly affluent Californian area. Basically, people from outside the US would make an account, and use the only Zipcode they knew. Beverly Hills 90210. (From the TV show of the same name) 20.4k
    via r/AskReddit
  • 12
    Text - OlmecDonald · 1d O 3 7 Awards Local casino issued a $20 free play coupon in the newspaper with no expiration date. I talked to the newspaper delivery guy and asked him about that copy and he told me he's got 100's of them in the van as they were a few days old now. I got all of them, clipped out the coupons and proceeded to make $19.50 every day after work for around 500 or so days. Not quite years, but pretty damn close. The casino never printed a coupon without expiration/one per custom
    via r/AskReddit
  • 13
    Text - 8bitPete • 1d 10 Awards Got keys to a new flat on a Friday afternoon, the place had electric but it wasn't in my name. Went to the electric company just before closing and the lady said "flat 8 you say.. Hummm we only have record of 7 flats on that building. Tell you what (glances at the clock) come back Monday with the serial number on your meter, and we'll get you all hooked up" I never went back and enjoyed free electric for over 2 years until i moved out. Edit to clarify: when I say '
    via r/AskReddit
  • 14
    Text - Solo_is_dead· 1d 5 Awards Circa Late 80s. You could make a long distance collect call from a pay phone, and charge it to a private number. The operator would call the other number to confirm. We'd ask the operator to call the number of another pay phone nearby,and have a friend authorize the call. Free long distance for almost a year. Reply 33.0k
    via r/AskReddit
  • 15
    Text - markydsade · 1d 8 2 Awards In the 1970s my dorm had one pay phone. My parents wanted me to call them once a week. I would make a person to person call to Toby DeSade, who was our cat. My mother would tell the operator he could not come to the phone. She would then call the pay phone. 7.2k ivy_tamwood • 1d 1 Award You have a collect call from "Dad,themoviesovercomepickmeup" 5.2k
    via r/AskReddit

    I used to do this with my friends when I didn't have a cell phone. The heavy collection of quarters my mother gave me were more useful for buying beer than a phone call. 

  • 16
    Text - lanni957 · 1d 149 Awards Used to work at starbucks like 7 years ago and they used to print these receipts where if you filled out a survey it would give you a 6 digit code which you could then exchange for a free drink. However when you gave in the receipt with the code we would just toss it in the garbage and then give the free drink. So over a shift I would just keep all the survey receipts when people didn't want them, write random numbers on them, then keep a wallet full of free coffe
    via r/AskReddit
  • 17
    Text - BarnabyMoose · 1d 8 4 Awards In high school, our p.e. grade was based on improvement. We took a skills test at the beginning and another at the end and your grade was based on how much you improved. So, once I learned that, I always sucked at the first test and then did miraculously better at the second, so I had a massive "improvement" and thus, a better grade. S Reply 1 15.8k ...
    via r/AskReddit
  • 18
    Text - IBeMadToo• 1d S22 Awards I used to live in an apartment across the road from a casino whilst at University. They released an app where if you "check-in" you get points that go towards free food and drinks. Because I was close enough to the casino I could just check-in without going to the casino itself. Every Saturday I used to get a free burger, fries and drink and watch sport in the sports bar. They eventually scrapped the app; it was awesome considering I was a broke Uni student. Reply
    via r/AskReddit
  • 19
    Text - FunklerLing • 1d S 11 Awards At my current apartment complex, they just changed the laundry machines so you need to use this super shitty slow app. I found out if you press start on the app and start on the machine and then back out of the app while it's "chatting" with the machine, the machine will start but won't charge any money. Been washing and drying for free for a few months.
    via r/AskReddit

    Laundry in the building and it is free? This person is really living the dream.

  • 20
    Text - WordN3rd • 1d 11 Awards Because I was a good student and rarely got into trouble, I was allowed to have my own phone extension in my room. So, if I was out past curfew, l'd call home. When my mom answered, l'd say, "It's for me. I've got it." And she'd think I was up in my room. She never did catch on. :D Reply 12.0k ...
    via r/AskReddit
  • 21
    Text - ArmyOfDog • 1d S 4 Awards The thing we clocked in on when I worked at Kmart would round to the closest quarter hour. So by clocking in 8 minutes early, and clocking out 8 minutes after my shift, I got paid for 30 minutes rather than for the 16 minutes. By exploiting this, I was paid 2.5 hours of overtime a week. Cumulatively, during my time there, this added up to about 6.5 weeks of extra pay. I wasn't ever caught, though. Edit: actually, since it was all overtime, it was closer to 10 wee
    via r/AskReddit
  • 22
    Text - lazyeyelefty88 · 1d 32 Awards Was living near & attending our local university. While working full-time in an economy in the midst of a recession I barely had enough money to pay the bills, let alone eat. Where I live is very well known for its tourist industry & casinos so I had quite a few friends who worked in it & would tell me about these MASSIVE employee luncheon cafeterias. At that time there were no id cards or lanyards to be scanned or checked, all you needed was to find it & be
    via r/AskReddit

    We miss the days when IDs were checked rarely, if ever.

  • 23
    Text - BakinandBacon • 1d S 6 Awards I grew up down the street from universal studios and went there everyday after middle school. Eventually we learned to go into the VIP line for rides which nobody was ever in. When the guy stopped us and asked us for our vip tickets, we just told them a high up employee named "Rick" should've called it in. After two seconds on the radio trying to verify, every employee just gave up and let us through. We skipped lines for years with that method, and eventuall
    via r/AskReddit
  • 24
    Text - One day we got bold though and snuck into the studio area. Guards caught us and asked us who we were with. We told him our fictional "Rick" told us we can be here. Well the guards took radio verification way more serious, and managed to get a real Rick on the line. We waited for Rick to show up, knowing we were busted. Rick showed up, turns out he was actually the backlot manager at the time and gave us a strange look. The security guard asked us if we were with him and this dude said yes
    via r/AskReddit
  • 25
    Text - WhatArcherWhat • 1d 3 Awards Photoshopped a college parking pass to hang in my rear view mirror, complete with a fake barcode. Even had it laminated. Free parking for 3 years, saved 250/year. Edit: if I was never caught does this still count? Reply 3.2k JustSomeVideoGuy • 1d 1 Award I got a parking ticket once at college but kept the envelope it came in. Then whenever I need to park somewhere I wasn't allowed l'd just stick it under my windshield wiper to make it look like they already go
    via r/AskReddit
  • 26
    Text - retrospect26• 1d 31 Awards I used to work at a grocery store and we had this era of the steak discounts. Hundreds of coupons for $5 off a steak were just everywhere for some reason. I found out that if I used the self checkout and bought a steak that was less than $5 while using the coupon, the machine would give me back the difference in change. I ate dozens of free steaks and filled my change jar up nicely.
    via r/AskReddit

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