25 Loopholes People Discovered That They Didn’t Mind Taking Advantage Of

If you stumbled upon a loophole in a system we all have to navigate, would you consider using it? A recent discussion on Reddit ignited curiosity around this topic when a user asked, “What’s the loophole that you discovered and subsequently exploited?” This question led many internet users to share their stories of accidental discoveries that worked to their advantage. Below, we’ve gathered some of the most cunning and popular examples from the thread, showcasing the crafty loopholes people have unashamedly taken advantage of repeatedly.

#1

Image source: CanadianBlacon, Shunya Koide / unsplash (not the actual photo)

I used to sell guitars at a music store. This guy started coming in and window shopping, getting prices. Didn’t seem serious so no-one wanted to waste time on him, but I was nice and maybe naive so I spent hours testing pedals, amps, etc. Writing out prices. He’d come in every couple weeks, telling me he has some money coming in soon. Everyone thought I was wasting my time, and after a while I started to believe them.

Then one day he calls and says he’s ready to buy, make sure I have everything he wants in stock for next week (it was around $1500 worth of gear if I remember correctly) when he comes in. I get his order ready.

Dude shows up with a huge stack of gift cards. Apparently the owner had been running a promo in the paper – go to this random record store, pay them $50 and get a $100 gift card to my guitar store. Could only get it once a week. This kid had been going to this place every week for like four months, buying gift cards and saving them up. Brought em in with this look on his face, like we are all idiots and he is the smartest MF around. And he was, there was no fine print, no limitations in any of the postings anywhere. Guy just got a monster discount for being patient. Im sure they lost money on that deal.

They don’t offer that promotion anymore, either.

#2

Image source: r_elwood, Getty Images / unsplash (not the actual photo)

My local car park costs 7£ per day…… but only 5£ if you hit the lost ticket option! I lose my ticket everyday!!

FoxyBastard:
My brother-in-law used to do this.
He would regularly go on business trips and the airport parking cost €25 per night but the lost ticket charge was €75.
He would leave on a Sunday night and come back on a Friday evening, having “lost his ticket”, and pay €75 instead of €125 every time.

#3

Image source: sorryqt, Erik Mclean / unsplash (not the actual photo)

When I was younger Mountain Dew had a promotion where 1 in 4 bottles won a free Mountain Dew. This was before codes and silly points, you just traded the cap for a new soda. I realized I could look through the plastic bottle at the right angle to identify winners. I only bought 1 soda that whole summer! It was glorious.

#4

Image source: FigBits, Ninthgrid / unsplash (not the actual photo)

A few years ago, Kelloggs had a promotion, where a box their new cereal included a coupon for another free box of cereal.

Presumably, the intention was that you would buy one and get one free. But you could use the coupon to get a free box of cereal that *included another coupon*.

So, I bought one box of cereal at the start of summer, and then continually used the coupons to get more of that cereal for the next several months.

#5

Image source: PM_ME_GOOD_VIBES_, Brooke Cagle / unsplash (not the actual photo)

When I started college, a family friend gave me a $50 gift card to a local coffee chain near my dorm, the kind of place that also has pastries and prepared sandwiches. I had very little spending money at this point, so this felt like a real windfall and I intended to make it last.

After 2 months of cafeteria food, I finally decided to splurge on a coffee and a muffin, the total is like $4.00. I hand over the gift card, and the girl on the register gives me this incredulous look. it was like I had just handed her monopoly money. Immediately this feels like it’s going to be an problem. She asks me where I got it. I tell her it was a gift. She rolls her eyes at me, clearly irritated. She says they don’t usually take gift cards, I guess they were pretty new at that point, but it was a branded plastic scannable card, obviously legit, so i politely ask if she can try it. She sucks her teeth and starts punching at the screen. 2 or 3 minutes of sighing and rolling her eyes go by and she appears to finish the transaction, hands me my receipt and throws the gift card on the counter without a word.

I’m kind of taken aback at this point by her attitude, but look at the receipt and see my gift card total is now $54. She credited my card with $4. I realize i’m trying my luck here but i quickly grab a sandwich and drink from the case and say, sorry i forgot i wanted to get these too. She rolls her eyes at me again and rings them up. The total is $12. Punches at the screen for a while again, prints my receipt – my new total is $66. Despite being a broke student, I probably would have pointed out the mistake if she hadn’t been so rude. Also I figured it was a one time thing, it couldn’t happen again, right?

WRONG. The next few months I got the total of that card up to almost $200.

I ate very well that semester.

#6

Image source: smoboaty, Ahmet Kurt / unsplash (not the actual photo)

In high school we had a fairly expensive cafeteria and I ate A LOT as a teenager. We also had a yearly fundraiser for the school that auctioned off things like the best parking spot, front row at graduation and free lunch for the year. After my freshman year my mom smartly added up all the money I had spent on lunch the past year and decided that was her limit on trying to win the free lunch in the auction.

She got it easily.

I burnt that place to the ground my sophomore year and again my junior year taking full advantage of that unlimited lunch.

They did not offer the lunch deal at the auction when my senior year rolled around.

#7

Image source: RyFromTheChi, Khanh Nguyen / unsplash (not the actual photo)

A few years ago, The Cubs had a promotion with Qdoba where if the Cubs scored a run in the 6th inning or whatever inning it was, you’d get a free burrito. When you walked into the stadium, the workers would hand you this little booklet that had the Qdoba coupon along with others. So many people would just discard them on the ground by their seats. After the games, I would go around and collect as many as I could find. I’d take them into Qdoba and get me free burrito regardless if the Cubs scores in the correct inning. The employees never checked or knew. So many free burritos that summer.

#8

Image source: Givemeananswer61, Hanny Naibaho / unsplash (not the actual photo)

I took advantage of a retail websites online gift card sale. They were offering “gift cards” for 25% off, for a weekend sale. The great part about it was that they weren’t actually gift cards they were just codes that they emailed to you to act as gift cards, allowing you to use it instantly. Well… it turns out you could buy gift cards with gift cards, for any amount. So my 17 year old self turned $20 into $650, over the course of about 4 hours and bought a brand new snowboard set up! I have never seen them run that sale again.

#9

Image source: anon, Shan A. Rajpoot / unsplash (not the actual photo)

I used to work in an office building downtown. Parking was expensive. Most places were about 10 bucks a day. So approximately 200 bucks a month. A bus pass for the month was about 80 bucks.

Then i discovered the casino paradox. If you parked at the casino, it cost 10 dollars. Expensive right? If you signed up for a casino club card, and you spun 10 dollars worth of slot machine, parking was free. Usually, you’re left with about 6 bucks out of your original 10. Bad if you’re purely gambling but now parking costed you 4 dollars.

Things got even juicer when the local sports team had a coupon for 5 dollars in free play on the back of each and every 50/50 ticket for an entire season. Since everyone loses they left their left over tickets all over, which I picked up. Now, with my free play money, I was technically getting paid to park downtown!!

#10

Image source: prevAlurker, Andreea Pop / unsplash (not the actual photo)

Pizza Pizza app. Had a promo flyer arrive on a box for a free pound of wings when I spend 9.99 when they were doing a scratch and win promo. Added the code. Ordered the a large 9.99 pizza and got the wings. The Pizza Pizza app has a “repeat last order” and it would automatically add the free wings every time I repeated last order. Then it gave me 2 dips on the scratch, so that was included. Then dessert. Then fries. then boneless bites. Just kept adding free promos on top of older free promos and I would keep repeating previous orders and adding more free stuff to it.

I accidentally updated the app. They fixed the glitch. It was a blessing in disguise cause I was eating way to much pizza every week. At least that’s what I told myself. It was a sad day. Now it feels weird paying for pizza from them.

#11

Image source: doctorwhoobgyn, Andrej Lišakov / unsplash (not the actual photo)

Bought a mattress on Amazon back in November of last year. It was one of those where they ship it compressed and it takes a day or so to fully expand. Anyway, the wife and I slept on it and it was rough on our backs, so we decided to return it within the 60 day trial period. UPS wouldn’t take a now fully inflated king sized mattress, so Amazon refunded our money and just told us to keep it.

#12

At my work I found out that if you scan your name badge at the till it counts as a transaction.
One of the things that can get counted on your annual review is your customer per hour rate, which is utterly random if you get things like old people writing cheques, people with no money insisting they really do have money in their accounts, finding item numbers for stuff that won’t scan, etc.
Solution, scan your name badge in between transactions to bump your numbers way up for when you get people who don’t have their s**t together.
Even without my trick I could average a 70cph and managed to bust out a 83cph without someone packing the orders for me. I just like my buffer zone.
I only told two cashiers I liked how to do this before I left the cash tills.
Company still hasn’t caught on.

Image source: Kootenaygirl

#13

Image source: LaunchesKayaks, Kenny Eliason / unsplash (not the actual photo)

There was a vending machine on my university campus that would give you two candy bars for the price of one. You would type in the number of the thing you wanted, then put in the money, then type the number again. It was amazing, but got fixed after a semester. :/.

specialkk77:
The vending machines on my campus were always broken. Eating money, items getting stuck…these things sucked. It got to the point where you could just go to the office and tell them “yeah, I’ve lost 20 bucks to the machines this week”, and they’d just give you the money. They relied on the honor system, since they were well aware that the machines sucked.
Sometimes the vending machine gods woul call forth a double offering to us poor college students. Those were fine days indeed.

#14

Image source: anon, Getty Images / unsplash (not the actual photo)

My company books me a flight home frequently when I am working out of town. But won’t book me a flight to a different destination, say I want to go to Vegas instead one weekend. So I let them book my trip home, under my rewards account. Then I go in and cancel the flight and use the credit to rebook it. I don’t know if they know this, but they’ve never said anything.

#15

Image source: SheZowRaisedByWolves, Ivana Cajina / unsplash (not the actual photo)

Story passed down from class to class by one of my biology professors, so read with suspicion.

It’s the day of a practical and someone shows up in flipflops. Universities don’t f**k around with lab safety (or at least just mine) and open-toe shoes are banned in the lab because– you know– acids and such. Even though no chemicals were out, the professor still wouldn’t allow the guy to take the test. The guy asked if he could borrow the thing of black tape that’s used to mark test tubes (kinda like duct tape but not as strong) and leaves the room. He comes back before the practical starts with both of his feet completely wrapped up to his calves with the tape and some crudely drawn on shoelaces with a pink sharpie. The professor has a chuckle and starts the exam.

Apparently, the head lab person catches the guy leaving the room and immediately takes him to her office to go in on him (then later called in the professor). His excuse was that he was poor and that they were orthopedic (he f*****g taped over his flipflops). Since there was no concrete definition of what closed-toe shoes were in the rules for labs, the lab tech angrily lets the guy go.

#16

Image source: nathan4597, Andrej Lišakov / unsplash (not the actual photo)

There was one website that I would buy from a lot that would cancel a lot of my orders because they were out of stock. I realized that they were refunding me twice for every order. I decided to do the right thing and tell them. I called them and the customer service agent told me “Happy Birthday”. I guess he didn’t care and I wasn’t going to fight him about it. I ended up with about $2,000. I guess I could have gotten more money out of this but I just felt bad doing it.

#17

Image source: anon, Getty Images / unsplash (not the actual photo)

I once signed up for a Firestone credit card.

I got my oil changed on our cars and new tires. I kept waiting for them to send a bill, and they never did.

I also told the cashier multiple times about not getting bills.

I also kept charging car stuff… Never paid once.

Nothing on my credit report, nada.

It’s been ten years.

weedful_things:
In ten years you will get a bill for $400 in service and 40,000 in late fees and interest.

#18

Image source: NoApollonia, Curated Lifestyle / unsplash (not the actual photo)

Local pizza place hasn’t been collecting the coupons nor expiring the code for 50% any online order. We’ve been using the same code for over a year. I couldn’t even tell you where the coupon actually is right now.

Before the hate starts, we still tip nicely. I at least half-believe the delivery drivers aren’t asking for it since we tip well and we get food from there far too often.

#19

Pizza Hut misprinted buy one get one free coupons. Instead of “less or equal value” on the second item, they said “greater or equal value”

So you could order only breadsticks and get a free large supreme pizza.

Image source: Flynn_lives

#20

Image source: BaronThe, Getty Images / unsplash (not the actual photo)

I had a 50% employee discount on my satellite subscription years after I left my old job. It was a s***e job.

Transplanted_Cactus:
I still get 15% off my cell bill for a corporate discount at a place I haven’t worked at in over two years. Apparently they never verify that you actually still work there.

#21

I bought beer once at the grocery store using the self checkout line. When you ring up booze on the kiosks, it’ll say it’s calling for an attendant so they can check your ID. When the lady came over, she looked at my ID and then hit the top corner of the screen, input a four digit code and then typed in my birthdate. I saw her code. So now whenever there’s a long wait at the kiosk (because there’s only the one lady for about ten machines) I will just put in the code and my birthday myself. Oh and you have to make sure you turn off the volume on your kiosk or it will say “ID check required” very loudly. I’ve only done it a couple times but nobody has stopped me.

Image source: anon

#22

Image source: massivelight, Getty Images / unsplash (not the actual photo)

Years ago, Wawa had emailed coupons for free cup of coffee. I had to print it myself cuz for some reason it wouldn’t scan on my phone. So I printed it and used it and got my free large coffee. All good so far.

Then I thought it’d be worth trying to print again and use it. They scanned the bar code so I thought the system would definitely know if it has been used. Guess what? That wasn’t the case. I printed coupons and made copies. My brothers and parents love Wawa coffee. We used to print the coupons and use it EVERY morning for 7 months.

#23

Image source: Eddie_Hitler, SumUp / unsplash (not the actual photo)

Expenses at my previous employer.

We had a hard limit of £20 per day for breakfast and dinner only, or it could be averaged at £20 per day or under for the entire trip e.g. you could spend £40 one day, nothing the next, then £10 one day, then £30 another. Lunch was **not** included for some very odd grandfathered reason that was long since lost to the mists of time.

The expenses category was for “Meals & Sustenance” which you had to book your breakfast and dinner to, although hotel-inclusive breakfast didn’t count towards the limit at all.

However, here’s the interesting part: there was another category called “Incidental Spend” which was unlimited. Guess who used this to purchase lunch items *and* breach the rate cap for other meals?

Me and about 26,000 other employees, as it turned out. Nobody was ever disciplined (providing you didn’t completely take the p**s) because HR amazingly admitted that they had screwed up and hadn’t thought of this being a problem. Took them two years from me starting before that was closed off.

#24

Image source: MontgomeryKhan, Andrej Lišakov / unsplash (not the actual photo)

A British price comparison website offers 2 for 1 cinema tickets for a year if you buy insurance through it. The cheapest possible insurance on there works out significantly cheaper than just a single cinema ticket.

#25

Image source: Asylem, Francisco De Legarreta C. / unsplash (not the actual photo)

When I was broke I forgot to disable auto-renew for x-box Live so when the charge hit my account, I had to call them and ask for a refund. Super simple process and I had my money back the next day.

And to my delight they forgot to remove my Live access.

I had it for a whole year. When it was time to renew, I paid, called them the next day to cancel, and sure enough had free x-box live for another year.

Scaphismus:
I once got an email from Microsoft saying “Thank you for your purchase of ($70 worth of Live points)”, when I hadn’t used my account in over a year.
So I immediately emailed both Microsoft and PayPal, informing them that I did not authorize this purchase, and I would like to reverse it. Paypal reversed the charge right away, so my account was all square.
Then, a couple of weeks later, I get another email from Microsoft apologizing for the mistake, and refunding my $70. The $70 that PayPal had already credited to my account.
I waited a few months before taking the money out of PayPal, thinking that they’d figure it out eventually, but they did not.
Thanks for the $70, Microsoft!