Loopholes—like holes in Swiss cheese, they’re everywhere, and they’re giving some people real-life cheat codes that border on dishonesty and even stealing. But you need to be very perceptive and to have the cunning of a Slytherin to notice and use them to your advantage.

Redditor SterlingBoardman asked their fellow internet users to share what loopholes they’d exploited for years before someone found out. Some of these are devilishly delightful and we’re not sure if we should be angry or impressed. Check them out, dear Pandas, and give the ones that impressed you an upvote. Let us know what loopholes you’ve exploited in life in the comments and what you think about people who use them in real life.

However, just because something is technically allowed doesn’t mean that it’s done in the Spirit of the Law. [Add holy chanting sounds.] While loopholes can help some people live a better life, others can use them for less than admirable purposes. And, in some ways, using loopholes is a lot like cheating. Besides, somebody ends up getting the short end of the stick in most cases. Whether it’s a small mom and pop store or a mega-million multinational corp.

#1

People-Share-Loopholes-They-Exploited 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 coffee. Since I already got tons of free drinks, I would give them to homeless people and explain it was good for a free coffee. Probably gave away like 100 free drinks.

lanni957 , HermanCheah Report

veveve
Community Member
2 months ago

that's very nice of him, all the extra efforts for other people

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#2

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 lived in downtown Boston for 310 dollars a month while I went to college.

Johnsendall Report

H Edwards
Community Member
2 months ago

This is very enterprising.

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#3

People-Share-Loopholes-They-Exploited 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 eventually ride attendants came to know us and just let us through. It was beautiful.

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! He took us aside and asked us what we were doing and we told him we just loved film and the studio atmosphere. He loved that two young kids were interested in his job and began taking us all around to the studios, allowing us to sit in on tapings of various shows and so on, giving us a free pass to come back anytime, and also....vip line access.

BakinandBacon , NBCUniversal Report

alex but festive
Community Member
2 months ago

and then everyone clapped

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SterlingBoardman’s thread got 64.7k upvotes and several hundred awards on Reddit. This just proves that the question they shared on the Ask Reddit subreddit was unique, out-of-the-box, and got our noggins jogging. It really made us think long and hard about using and abusing loopholes and whether it's right or wrong.

Personally, I’m a big believer in the Spirit of Justice. Not all rules, laws, and regulations are just and good. Similarly, not all things that are just and good have been written down and packaged in a neat and tidy stack of papers.

That’s why we use our common sense and why we have cultural customs and conventions (known as mores) to help guide our morality and how we behave in society. In other words, life is never as easy as following the rules as written. You can’t shut off your brain and your sense of what’s right. That’s why some legal loopholes can make us feel guilty inside—we know we’re doing something wrong by ‘gaming’ the system.

#4

People-Share-Loopholes-They-Exploited 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.

btpn-425 , denebola2025 Report

Aleksandra Elias
Community Member
2 months ago

this kid businessed!

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#5

People-Share-Loopholes-They-Exploited 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.

IBeMadToo , stu_spivack Report

wandile dludlu
Community Member
2 months ago

That's an awesome story

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#6

People-Share-Loopholes-They-Exploited My Aunt and Uncle were trash collectors both professionally and as a hobby. My mom had pulled one of her epic [screw] ups (again) and we ended up living with them.

Most of our food came from the trash, however Dominoes had a rewards system where the boxes had blue or red tabs depending on the size of the pizza.

Collect enough tabs, get free pizzas.

Aunt and uncle collected thousands of those tabs. We ate pizza every weekend for months before the company caught on and they put an end to it. I was 11 at the time but I remember hearing that their address was banned for life from delivery. I'm pretty sure Dominoes also stopped the promotion shortly thereafter.....

It was awesome while it lasted.

MissSassifras1977 Report

Stille20
Community Member
2 months ago

I get that they were taking advantage, but they followed the rules. So dominos needed a new system.

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In case you needed more persuading that loopholes aren’t all that Legal (notice the capital ‘L’) even though they’re legal (small ‘l’), Investopedia defines them as technicalities that let people or businesses “avoid the scope of a law or restriction without directly violating the law.”

You might not be breaking the law (technically), but you’re using a “flaw or defect” in it for your own gain because the people who drafted the law didn’t see the cracks in the legislation. The fact is, loopholes get closed all the time as some glaring limits of rules and regulations become obvious over time. No law will ever be perfect, so it’s a constant uphill battle against those who find the teeniest loopholes they can exploit.

And though it’s all fun and games on a small scale when you get a free burger because of some quirk in the rules, it can lead to some seriously dangerous things like tax evasion because of how complicated (and full of loopholes) things like tax codes are. At the end of the day, it’s up to us to decide if we use loopholes or end up relying on our conscience.

#7

People-Share-Loopholes-They-Exploited 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, I'd call home. When my mom answered, I'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

Edit: It was 1976. My mom never knew. I know that because I confessed to it years later. She was very shocked and mad, and she grounded me. But I was forty and had my own house by then. My parents were the early-to-bed and early-to-rise type, and my room was a converted attic two floors up from the rest of the bedrooms. I often came home after everyone else was asleep because I had a part-time job, so I was used to sneaking in like a ninja. It was a bright yellow Princess phone. And finally, I knew a good thing, so I did not abuse this technique, just a few times when it was absolutely necessary, like the time we hitchhiked to see Peter Frampton.

W0rdN3rd , Noisy Little Monkey Report

Becca Gizmo the Squirrel
Community Member
2 months ago

This is brilliant.

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#8

People-Share-Loopholes-They-Exploited 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.

BarnabyMoose , Peretz Partensky Report

Acceber
Community Member
2 months ago

Used to do this in PE all the time (not for grades but our bleep test results were read out infront of the whole class so as long as you did ok to start it was fine). Except once I was ill that day and only got to about level 3 before having to pull out (literally threw up as soon as I stopped) and that got read out and eveyone laughed how crap it was because the teacher didn't note I was ill

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#9

People-Share-Loopholes-They-Exploited Arby's used to have a "take a survey on the back of the recipt and get a free roast beef sandwich". But when I got the free one, I got a recipt then too. I bought one sandwich got literally dozens for free over the course of a year or so.

MermaidRumspringa , Mr. Blue MauMau Report

Aahzmandus Pervect
Community Member
2 months ago

If this is true, that was such an obvious loop hole that some one at Arby's must have been a blithering idiot to allow this to happen, for a year or so. But somehow I don't think this is a true story.

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#10

People-Share-Loopholes-They-Exploited 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 dressed appropriately to the employers dress code. After my friend & I did a dry run on one of those trips, in order for me to find it without getting lost I would go it alone. For almost 3 years I had lunch/ dinner for free, learning the peak service times & the dead zones. Even got along with some of the cafeteria workers and custodial crews.

lazyeyelefty88 , Smylers Report

zims
Community Member
2 months ago

Speaking as someone who did setup/breakdown for these kind of events, this is actually fine. As long as it's not the kind of event where they get individual lunches per person, they typically order a lot more food than gets eaten. Sometimes you get people to eat up the leftovers, but often enough you have to throw perfectly good food in the trash at the end of the day. Please do take the extra sandwiches off our consciences.

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#11

People-Share-Loopholes-They-Exploited 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.

retrospect26 , sousvideguy Report

Adam C
Community Member
2 months ago

wow you got PAID to eat steak.. ..what a dream

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#12

People-Share-Loopholes-They-Exploited 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 I 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 new address. A half-dozen times over the next few years, I went and got free stuff with all the points that I kept racking up as one of their most loyal customers.

otternoses , Northwest Retail Report

Anarchy (they/them)
Community Member
2 months ago

I wonder if that would work where I live...

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#13

Way back when, I did the grocery shopping for my large family as a teenager. Mom didn’t drive, dad didn’t shop. I drove, so she send me for groceries. Deal was I could keep the coin part of the change from the purchase for doing the shopping for the family. Didn’t take me long to figure out to ask for a $10 roll of quarters each time when I was given change. Went on for a few years; Mom didn’t know about it until I fessed up in my 20’s. “You little s**t,” she said while laughing. I miss her.

capnvontrappswhistle Report

MauKini
Community Member
2 months ago

I am sorry for your loss.

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#14

People-Share-Loopholes-They-Exploited 2
Obligatory not years but I can't believe I got away with it- My mum gave me £20 to buy a big thing of a certain brand of cat food which normally costs £10.99. Now heres the thing- when I entered the store I was given a coupon for £5 off that particular brand of cat food. The store was ALSO doing £5 off the type of cat food I entered for. I got to the till and the food was priced at £5.99, I handed over my coupon and it was scanned so that the food was 0.99p. I couldn't believe my luck because normally it says "not for use in conjunction with any other offer". But here's the real kicker - the lady behind the till gave me ANOTHER COUPON so you can bet your goddamn life I went round again and left the store with £22.98 worth of cat food for £1.98, with a third coupon in my hand. The only reason I didn't keep exploiting the loophole was because I had to carry it all home on my BMX

InDarkestNight , Don DeBold Report

JessG
Community Member
2 months ago

Totally store’s fault. Lots of stores accept double coupons, if you’re smart enough to figure it all out, you deserve the reward

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#15

This is super weird and I haven’t thought about it in years, but I suppose it was a loophole... Soda companies used to run giveaways where they would put a code under the cap and then you could enter the codes for points, and get free stuff once you had banked enough points. I was a stock boy at a local grocery store and we had to take care of the bottle return machines also. Any loose caps (and nasty soda juices) would settle in the bottoms of the bags, so on slow nights we would cut the corner of the bags to drain, and collect any loose caps which I would then wash in the mop sink and take home to bank the codes. I ended up getting some sweet stuff like a few CDs, a zip up sweatshirt, and even some decent noise cancelling headphones lol

DannyHeitz Report

JP Doyle
Community Member
2 months ago

Did the same thing as a janitor. Always found the pop caps on the floor or in the parking lot. Snagged a lot of cool discounts that way.

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#16

Staples used to let you recycle an infinite amount of ink cartridges at $2 a pop. My old job used to run through ink cartridges at an insane rate and it happened to be my duty to recycle them. I brought them to Staples and recycled them under my Staples rewards account to what amounted to 1000s of dollars over time. If there wasnt something in the store I wanted to buy with the coupons, I could buy from their online store which had video games, tvs and other non office items. If I still didnt see something I wanted, I could buy a Visa giftcard or giftcard to another store via their website to translate the money in to direct cash. Staples eventually put a 10 cartridge per month cap on recycling which ended my madness. All technically legal mind you.

DrowningInFeces Report

Stille20
Community Member
2 months ago

Your old job wasn't paying attention. It could have gotten you fired because technically it's not legal or ethical.

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#17

Not years, but when I was broke and had just relocated to a new city, I couldn’t afford WiFi for a few months. The first weekend I was laying around my apartment playing on my phone, and I noticed there was a WiFi network in range that was named ‘Gandalf.’ Well, I attempted to join and after being asked for the WPA, without hesitation I plugged in ‘youshallnotpass’ and was surfin’ the web for free for the next few months.

jeanyanndecannes Report

ML
Community Member
2 months ago

Some things are loopholes, but this is illegal.

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#18

People-Share-Loopholes-They-Exploited Part-time retail worker for big chain.

Work gives employees a 5% discount over all purchases, increasing to 10% on store products.

Gift cards are store products. So are vegetables and a lot of groceries.

By paying $45 on a $50 gift card and then using said card for my shopping, I can purchase $55.55 in groceries, for an effective 19% discount on almost all my essential shopping (and 14.5% on everything else). I have on occasion bought a card online on my phone while queueing at the checkout.

Four years strong and still wondering when they’ll realise they’re giving me a discount on money.

Ediwir , Phillip Stewart Report

Jonathan
Community Member
2 months ago

Lucky them. Many moons ago I was a retail worker for a supermarket chain and they were that tight we never got any staff discount!

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#19

People-Share-Loopholes-They-Exploited 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 customer rules ever since.

OlmecDonald , dmdonahoo Report

Adam C
Community Member
2 months ago

haha "the house always win"

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#20

People-Share-Loopholes-They-Exploited I'm still exploiting this one:

Whenever I need a shoulder and neck rub, I offer one to my partner.

He usually accepts, and I spend some time rubbing his shoulders while we watch TV. Then we switch and I get an awesome rub.

I find that if I just ask for one he will definitely do it but loses steam after a few minutes. I think when I give him one first it loosens his muscles up so he's more relaxed, plus maybe he feels more obligated.

I intend to keep on exploiting this for as long as I can.

aliasbex , whitesession Report

Stille20
Community Member
2 months ago

eh, I don't know that you want to use loop hole or exploiting as terms for what you do in a relationship.

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#21

People-Share-Loopholes-They-Exploited At my current apartment complex, they just changed the laundry machines so you need to use this super s**tty 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. App name is similar to smallGS or smallPayments

FunklerLing , Barb Report

JessG
Community Member
2 months ago

Stupid app

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#22

Bank of America would give you 3% cash back points on gas purchases. Back when I did this, I was a heavy smoker, and realized by coincidence that if I paid for gas inside and made other purchases, that I would still get 3%

So buying like $1 of gas and cartons upon cartons of cigarettes became my thing.

Now I dont smoke anymore though, which is even better savings :)

Rellikx Report

PearlsNotSecretRapCareer
Community Member
2 months ago

Good job!

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#23

People-Share-Loopholes-They-Exploited Whole Foods used to have bacon on the Breakfast Bar. Cooked bacon weighs almost nothing! I would get a pound of cooked bacon for $8.00 It lasted almost a week! Bacon crumbles for the salad, for the turkey sandwich, and the 100 other things that you can toss bacon into!

I used this method for almost a year, then they stopped putting bacon out....sigh......

Eponarose , cyclonebill Report

Stille20
Community Member
2 months ago

Aside from slowly killing you, yea, that's totally within the rules. high five for cheap bacon!

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#24

People-Share-Loopholes-They-Exploited 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 3 months as it was regularly empty, basically paid for my drinking and more for 3 months!

mammoth200 Report

Adam C
Community Member
2 months ago

I got banned years ago when I always win in this little pizza places. "you eat pizza for free AND take my money...never come back".

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#25

About 10yrs ago American Eagle distributed $10 off $10 purchase coupons on my campus. No restictions. I asked nicely and one of the reps gave me a STACK of them. Guess how much socks and underwear were? $10.50. It was years before I ever paid more than .50 for a pair of either. Sunglasses were like $2. Flip flops. The accessories world was mine for the flaunting.



Never saw that deal again.

TheLastPeacekeeper Report

JessG
Community Member
2 months ago

Hey, if the Rep. gave them to you, it’s not stealing

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#26

When we had a daily limit of one hour on our AOL account my sister figured out if you unplugged the phone line during your session and logged back in it reset your hour

zamboniman46 Report

JessG
Community Member
2 months ago

Oooh, good one

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#27

People-Share-Loopholes-They-Exploited At my old job we had a vending machine in the basement that gave change back when you bought something. Sometimes it gave more than you paid. No one used this machine as the basement was being reconstructed but it was regularly filled.

EarlyBirdTheNightOwl , ashish joy Report

You are Beautiful
Community Member
2 months ago

Grandmas

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#28

People-Share-Loopholes-They-Exploited 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.

ArmyOfDog Report

A.M. Pierre
Community Member
2 months ago (edited)

I can see it being fairly easy to leave exactly 8 minutes past your clock out time, but checking in exactly 8 minutes early? That's super precise, and makes me think you would end up getting there earlier than that but lingering until exactly 8 minutes before check in to actually click the time clock. And what's the point of getting there early enough to get the extra time but not actually clocking in until you only have 1 minute to spare and might miss your window? Edit: I'm sorry that I wasn't clear - I am NOT judging this person or saying they were right or wrong to do this. I'm asking why they made it harder on themselves in a way that made it more likely they wouldn't get paid for their extra work every morning.

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#29

People-Share-Loopholes-They-Exploited 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.

Solo_is_dead , Ted Duboise Report

Rose the Cook
Community Member
2 months ago

Weren't the numbers of pay phones different to private home numbers? If they were, did the operators not recognise this or just not care?

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#30

People-Share-Loopholes-They-Exploited 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.

8bitPete , Jason Woodhead Report

Guy Levin
Community Member
2 months ago

Hmm yeah that wasn't free, you were probably connected to a neighbor's meter and they paid for you, unknowingly. That's illegal in most countries, and a pretty shitty thing to do.

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