30 Stories Of People Finding And Exploiting Loopholes

When my son was in high school, he went to one that was connected to the community college. Starting in 10th grade, he could take college classes, so he chose classes whose credits would apply to both high school graduation and an associate degree. He also favored accelerated 7-week courses. He graduated high school with an associate degree and transferred 49 credits to his 4 year university.

When I was in high school, I accidently found a soda machine that dispensed free grape soda. I hit the button randomly while passing by, and a grape soda came out. I did it again the next day just to see and more free grape soda. It must have been busted or some sort of strange glitch. For the entire school year, I would pass by and hit grape on my way home and get a free grape soda. I wasn't stupid about it either. I kept that s**t to myself. I wasn't about to ruin my free grape soda by telling everyone.

It's pretty minor, but Fuddrucker's kid's hamburger meal was less than half the price of the regular burger combo, so I'd just buy two kid's burgers and fries and end up with more food than if I'd gotten the regular burger meal. And I'd get two cookies.

This loophole I learned from someone else on reddit but i’ll share it for those who may not know: If you have a planet fitness plan and can’t cancel it online, change your home gym to a random one in California. Then you can cancel it online!

Got fired two weeks after HR got fired. They never cancelled my health insurance. That was 2001.

When my brother and I lived together, he worked for a large chain restaurant. They had a policy where if someone called in an order for pickup and didn't pick it up by closing time, it was free game for the employees to take home. Occasionally, I would call in orders for pickup, never pick it up, and he'd just take it home for us. I'm not proud of it. We were both broke af at the time, and most days, it was the only food we could get

EDIT: I'm no longer broke so whenever I buy food from this place I make sure to leave a heavy tip, I guess as a thank you to the chain for keeping me alive but mostly to ease my guilt.

I used to bartend and would have to pay for parking, either on the street (which was a pain since I would have to re-up in the middle of my shift and often forgot), or in a paid parking lot.

Found a parking garage that used a ticket machine on the way in, but had you pay a person on the way out. 90% of the time there would be no one working late night when I left work, so I scored free parking for a few years.

I was leaving an abusive ex, and he had made me put our apartment only in my name. I was gonna have to pay a bunch of money to break the lease. Until I looked at it and realized to my had put the wrong year for the lease ending. They had done the year before, so legally my lease was over and I had technically been month to month. The manager was super pissed when I pointed this out, and that I did not have to pay any lease break fee or additional rent past my submitted move out date. They tried to hit me with a bunch of maintenance and cleaning fees after. But I had picture proof the place was in the exact condition I’d rented it in. So they informed me I would never be able to rent at any of their properties again. Which was super dumb. I’ve always been a really great tenant anywhere I’ve rented and I was not going to let them do anything legally that could f**k me over. Buuut that whole lease thing was a huge relief and very helpful during the worst time of my life.

When I was a struggling single Mom there was a well known rewards program that ran a promotion that you would get 3 points for every “review” posted on business listed on a business directory website.

I wrote reviews non stop for months, always gave 5 stars if it was somewhere I hadn’t been (figured the business owners would be happy with that) , and everywhere I did go I wrote an honest review. I worked my way through the alphabet and after a few months I was able to buy my son a PlayStation for Christmas with the points.

Around 2008, the US Mint was trying to get more people to use the new dollar coins. You could buy some via their website and they would ship them to you for free. Those purchases would earn you points on your credit card.

I bought $10,000 worth of coins, then took those coins to the bank so I could pay my $10,000 bill. I would then buy another $10,000 and repeat. A few hundred thousand air miles later and I’m still using those free miles in 2024.

They eventually did close the loophole, but some people with huge lines of credit were able to get millions of free air miles.

When lava cakes first rolled out on the dominos app, rather than selling them only in two packs as they do now, there was a drop down picklist where you could select the specific number of cakes you wanted. For whatever reason, if you selected 1 cake only, it was added to your cart with no price ($0.00). You could then go into the cart and change the quantity of that $0 lava cake to whatever number you wanted.

I was worried at first that I'd get found out so I would only order 1. Then I got bold and ordered two, and they came just as they do now, two in a pack. No charge. I decided to push it one time and ordered 8 lava cakes with just two medium pizzas. Total bill was $16. Thought for sure someone at the store would realize something was wrong sending out two pizzas and 8 cakes for $16. Nope, minimum wage employees don't give a f**k, they just see the order and fill it.

After that I was like the Don of crunch cakes, you want a crunch cake? You GOT one. I must have gotten hundreds of those things over the course of 3-4 months. Eventually I knew it would come to an end. I was going to write to dominoes in hopes they'd like give me a gift card or something for exposing the glitch, but my gf at the time was like dude, don't blow your cover, they'll just fix it and not give you anything, so I didn't.

Less than a month later they patched the problem, and I still regret not being the whistleblower and maybe getting some free pizza.

As a totally random button on this story, years later I was helping my company develop their website, and I flew to Detroit to work directly with the developer. At lunch on the first day we were talking shop, and the dev told me one of their claims to fame was developing the Dominoes pizza tracker. I was like, wait, did you just do the tracker or the whole site? Turns out they did the whole site, the app, and tracker! I mentioned my lava cake scheme and the dev almost fell out of his chair, he was like "I totally remember that issue and patching it!", he was floored I had the inside scoop on that site glitch he assumed nobody knew about.

I used my college ID nearly until my 40s for discounts.  A few years back, a cashier at a local hardware store gave me a "really" look that cut right to my soul which made me stop using it.

I used to fish a lot. WalMart guaranteed their trolling motor batteries for 12 months to charge to I think 90%. So I bought 3 batteries for $125 each and kept the receipt. At month 11 I’d go in and have them tested and without fail they’d be in the 80% range and I’d get new batteries with new 12 month warranties, that’s how they wrote the policy. Finally in year 6 they gave me my new batteries with a 30 day warranty. But I got 7 years of new batteries and used the final 3 for 3 years.

There used to be a glitch in my Domino's app that would give free extra cheese as long as you waited until it asked if you wanted it. If you added it yourself it would charge you. It worked for a few years until I got a new phone.

It was a multi step process but damn it felt good. A local grocer had coupons for $1.00 off a 32oz Gatorade, branded by Gatorade, so they worked at multiple retailers. I clipped a bunch of them.

Then I went to Walmart down the street and loaded my cart with as many gatorades as coupons. At the register, the cashier was baffled I was buying so many gatorades (I was in high school). She scanned all my gatorades and the total was something like 68 dollars. Then I had her apply a price match to Meijer’s price, something like .88 cents each, bringing the total down a bit. But it doesn’t stop there.

Then I had her scan all of my coupons (deducting a dollar for each Gatorade in my cart). The look on her face was hilarious, as my ‘total’ went lower and lower each scan of a coupon, eventually passing zero and showing a negative value. After ringing them all up, she got smug and said, “I bet you think you’re pretty smart, getting all of these for free”. I looked at the total on the screen, then at her, and said “oh no, not free. I actually think I have some change coming back”. Her jaw hit the floor as she called her manager and was told, indeed, that she had to also shell ~$8 out of the register and hand it to me. What a feeling that was. [Proof of Gatorades](https://imgur.com/a/PTQTiAg).

When I was studying I used to take the train home almost every weekend. There used to be a perk with the first class ticket that you could rebook the train if you missed it in a 24 hour window after it departed. I figured that the only way they would know if I missed the train was that if they scanned my ticket. So I just put on something that made me look like I belong and then I pretended to be asleep when the conductor came to check the tickets. This worked almost always so I had two tickets, one for each direction that I just rebooked into the next week. The first class had single seating, free coffee, biscuits, oj and water. It was almost empty usually so very nice and quier, the train otherwise was usually aleays booked near full but people didn’t want to pay the 50% more for the first class. I think I got ”woken up” like 5 times during the 3 years I studied so I paid about 320€ for about 100 first class trips on those trains. I guess they realized people were doing this and it was changed as an optional addon to the ticket and had to be rebooked before departure.

I worked for an organization that ordered large amounts of groceries every week for their group activities from a major supermarket.

There was a place to put in your loyalty card number so I just used mine.

Not only did I get heaps of points to use in shopping there, no one noticed it until about five years after I left.

Edit:
- I wasn't a supermarket employee or other insider exploiting my employer. We were a totally unrelated business who bought from them.
- When I was tasked with setting up the account to purchase online there was a form to fill out. My business didn't have a loyalty card and wasn't interested in gettiing one. So I just used mine. It was a set and forget type of thing. The supermarket also had, in addition to our business landline, my mobile number and the delivery people would contact me directly if they had any problem at 6:30am when they brought the stuff.
- I don't really know if anyone ever noticed it or not. Probably either (a) they changed their supplier or (b) someone else taking care of the account put in their number instead (I tend towards option b). They didn't ask for the points "back" because they hadn't been interested in them in the first place.
- For years I also kept getting calls from various suppliers who somehow still had my mobile number - I kept redirecting them to the office and telling them I didn't work there any more. It hasn't happened for a while now.

This isn't exactly a loophole, it's more an unknown exploit.

In the UK if you work for a large business they have to spend 0.5% of the salary bill for the Apprenticeship Levy. They need to spend this money within three years or it's forfeited to the government.

One of the "apprenticeships" you can do is level 7. These are the level of a masters degrees. I got a £25k MBA for free, paid by my employer with zero strings attached.

I used to work at Staples many years ago and every item that we sell has a status. For example, A status stands for active, C status stands for clearance and F status stands for final. For whatever reason, when an item goes to F status, the price drops DRAMATICALLY. I'm talking a desk that was $250 would ring up for $8.50. Also, because it was no longer an active item, that meant it was no longer on display on the sales floor so anything that would not sell would just sit in the back unnoticed. I used to run a report in our system constantly and it would list everything that our location had in stock under F status. There was a time when like 1/3 of my furniture at home was F status items and I paid probably $50 total for it all. Got my first DSLR (with lens) for $250 (regular price was over a grand). It was a great time to be alive.

Signed up for a free trial on Audible, when I went to cancel it offered me a free credit to stay. Took the free credit, went to cancel again and offered another free credit to stay. Got about 25 credits in one day before I chickened out and officially cancelled.