“What’s The Best Loophole You’ve Ever Discovered?” (76 Answers)

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

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.

Image credits: Gal_GaDont

#2

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.

Image credits: Dreammy_Glitter

#3

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.

Image credits: Beautifull_Fairy

#4

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.

Image credits: Pilotx15

#5

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.

Image credits: Mermaid_sapphire

#6

Using a free trial with a new email every month to avoid paying for a subscription.

Image credits: Omnibusnew

#7

Back when soda companies would have promotions on the underside of the bottle caps, I could tilt the soda bottles just right so I could find winners. During many promotions, I paid for 1 initial bottle of soda, a “get a free bottle” winning one, then continually searched and found those never having to pay for a soda.

Image credits: ihadtopickthisname

#8

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.

Image credits: Babyygirlly

#9

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.

Image credits: WatchingInSilence

#10

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.

Image credits: AnAngryPirate

#11

Figuring out that if you bring a clipboard and walk with purpose, almost nobody questions why you’re there.

Image credits: Banes_World_Archive

#12

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.

Image credits: Gigglyy_Queen

#13

Transferring credit card balances between balance transfer cards until I no longer had a balance, it would push the payment dates back each time allowing me to save money to pay off more.

Image credits: ChaplinCrabtree

#14

Used the iPod Nano exchange programme with Apple to help pay for my first property. Send them an old Nano 1st Gen and they send you the latest version which I would then sell. Did it with ~1000 units. They did blacklist me towards the end.

Image credits: efwbphoto

#15

Pizza Hut recently had an exploitable deal in their app. They had a 2 items for $8 each deal (must buy 2) but I noticed that after I selected the first item (a medium pizza), it was already in the cart. I tried to check out and it let me. Boom.

The loophole is now closed but I must have fleeced them for tens of dollars over the past few years.

Image credits: lkmyntz

#16

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 ?.

Image credits: LeditGabil

#17

My brother got free parking for pretty much his entire time at university.

It was that golden period when the pay parking kiosks were able to accept credit cards, but before they were actually connected. They’d read a card and check it against a locally stored list of banned numbers, and once a month the meter maid would download the transactions, process them, and update the blacklist. My brother found that they’d accept those prepaid gift cards if they were backed by Visa or MasterCard, but couldn’t check the available balance, so he’d buy one, use the balance up on whatever, them use the card for parking until the end of the month when it’d get processed, found to not have funds, and banned. Rinse and repeat.

Guy saved probably $2500 over his degree.

Image credits: Chic_Femininee

#18

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.

Image credits: LordBaranof

#19

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.

Image credits: peanutbudderlover

#20

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.

#21

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…

Image credits: TechStumbler

#22

Working in a call center for a large phone company, clicking your mouse really fast on the screen caused it to go into some mode where it looks like you’re waiting for a call as normal, but you’ll never have a call come through. Some kid figured it out, and the trick spread to a bunch of people and was kept under wraps from management. We passed it down to others as we onboarded them if they were deemed trustworthy, haha.

Image credits: LiakaGold7

#23

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.

Image credits: bluegenes71

#24

I have over 26 GB of free storage in my Dropbox account.

Not sure if it still works this way, but like 15 years ago they would give you like +500 MB of space for each signup you referred, up to like 50 referrals (or maybe it was +1 GB and ~25 referrals?). But they had to actually install and activate the client for you to get the credit.

I set up a little Linux VM and created a save point with just a browser and an un-activated Dropbox client install in it. Then I used a bunch of throwaway emails to send a c**p-ton of referrals.

For each one I would boot the VM, process the next referral in the list, then (and this was the key) shut the VM down and change its MAC ID. Rinse and repeat. As long as the MAC ID changed, Dropbox saw each one as a separate thing.

I probably could have automated it, but I got the process down pretty good so I just spent an evening grinding through them while watching basketball or something. Took a couple hours total.

Image credits: cujojojo

#25

There was a shuffle you could do on the McDonald’s self serve screens where you’d add a cheeseburger and take all the toppings off, they’d refund a bit for every topping, and you’d be left with $-0.10 at the end. Do it like 50 times and you got a free meal. We did it once or twice to get a free drink in summer before they changed it.

Image credits: Bugaloon

#26

Back in 2013, Papa Johns had a promo for the Super Bowl where if you called the coin toss correctly, you would get a voucher for a free 1 topping pizza. However, the only control in place was you could only enter the contest one time per email address. I created more than 60 emails, half of them calling heads, half tails. Ate free for six weeks.

Image credits: MermaiddSapphires

#27

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.

Image credits: DrunkStoleATank

#28

Felt like a giant win for me…my favorite fast casual restaurant had a coupon at the bottom of their receipts for a free meal if you filled out the survey. I figured out the pattern of the code and brought in a new code every time. I was getting free meals like 2x a week for over a year.

Image credits: Bananas_are_theworst

#29

There was a loophole in Sweden on Libero diapers. They sent out coupons to new parents. And the coupons could be used in ”selfcheckout”, and you only had to scan it, and you could keep it.
So everytime we bought diapers we could use almost everyone weve got. Adding up to 50-80% off every time.
It worked for a year i think, before they fixed it.

Image credits: Detskullemanhagjort

#30

The electronic ticket I use has a loophole. It works by measuring the distance between stations via GPS. Cost will be a basic fee plus a set amount per kilometer.

If I go to the city it will automatically notice when I go back and start a new fare. But if I go back one more station than I started from it will only register a fare of one station in that direction. Saves me ca. 6€ every trip with my kid.

Image credits: Quarktasche666

#31

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.

#32

I got 30k for free. Disclaimer: not in US.

During my degree, I was on a full university scholarship that completely waived my tuition fees, provided I maintained grades above a certain threshold. This scholarship was offered directly by the university based on my strong academic performance in a national exam.

Separately, there was a government scholarship meant for students from low-income households. Since my family wasn’t well-off and I got strong academic results on the national exam, I qualified for the government scholarship. Knowing how disconnected government systems can be, there was likely no coordination between the government scholarship program and the university’s system. So, despite already having my tuition covered, I successfully applied and received 30k from the government scholarship—money I technically didn’t need because of my full university scholarship.

That’s how I ended up with 30k before I even graduated.

#33

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.

#34

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.

#35

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.

#36

We figured out that on our country’s biggest website for takeout food that if you go all the way to the payment screen, then click the ‘back’ button on the browser, not the website, enter a tip for the driver and then proceed with the process you only pay the tip and the order still gets delivered.

We did this twice and then the glitch was patched.

#37

Free cable TV

Once lived on a property in one of two homes that shared the same mailbox/address. One month I got behind on my cable bill and they came out to disconnect me and disconnected my neighbor’s service instead. Neighbors soon called me to ask if my service was out and I said, no. There was a big football game on that day that they had planned to watch and they were bummed.

A friend of theirs, who happened to work for a different cable company, was visiting and asked my permission to splice a cable between the two houses, so they could get service from mine and I agreed. Took him about 20 minutes and they were back in business in time to watch their game.

Once I’d figured out the reason for the original disconnect, I explained it to my neighbors – who then stopped paying their cable bill on purpose. Cable company sent out a bucket truck only to discover that their cable was already disconnected – and went away satisfied.

We then had free cable in both house for the next three years that I lived there- with both of us having been officialy disconnected.

#38

I discovered a loophole for finding a job very quickly, especially remote jobs.

job recruiters look for resumes by searching sites like indeed dice ziprecruiter etc.

Much like how you can SEO optimize a website to show up first in google, you can also SEO optimize your resume to show up first when recruiters search your targeted job titles on these sites

edit: for everyone asking how, i learned from the stickied post on /r/CSCareerHacking.

#39

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.

#40

Are there any pay phones around anywhere anymore? A long time ago I was using a pay phone when there was a blackout. The electricity came back on within 5 minutes. The phone started dumping all the change into the coin return space. I must’ve gotten 4-5 bucks! It was 1978 so 4-5 bucks was more then ?. I promptly drove to every other pay phone I could find. It was a good day!

#41

Eta – at work today, just on my break and it happened again. Must have sensed me talking about it ?

Theres a vending machine in the staff room at my job, and its a complete a*****e. Food often gets stuck, especially the bags of chips. If this happens, the machine does at least automatically refund the money if you paid by card. So you just buy another item, use it to knock the first one down, and boom! Two for one. This machine is staff only, but none of the items are cheaper because of it. They’re actually more expensive than the public machines. It has also stolen many peoples coins over the years, so I don’t feel bad for occasionally getting a “free” bag of chips.

#42

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.

#43

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.

#44

When I was a young ski bum we discovered phone operators counted the coins going into the phone for long distance calls to make sure correct amount paid. Quarters made one sound, dimes another… We tape recorded $20 worth of quarters going into a payphone (with pauses at $5 increments so we could keep track) and just played the tape when the operator told us how much call would cost. Worked like a charm all winter – our parents were quite impressed we weren’t calling them collect. And one of the guys in our cabin came from France.

#45

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.

#46

I joined the military for what was supposed to be a 6 year commitment. I was a reserve. Had to go to basic training and an “A” school (to be a radioman). that took 8 months and then I was released from active duty and had to go to meetings once a month and 2 weeks of duty in the summer. I found out that a reserve could only spend 2 years total of active duty. So, I said screw the meetings and just stopped going. That was, of course, not acceptable to them (U.S. Coast Guard) so they ordered me to active duty, on board a cutter ported in New York City (I had some fun there!). After 16 months they had to give me an honorable discharge. So I actually spent 2 years and 8 months total in the Coast Guard instead of 6 years. Worked out well.

Image credits: StationOk7229

#47

I used to bartend at Uno’s … every fall we’d sell gift cards for X-mas. For every $20 sold we’d give a $5 coupon that could be redeemed after the New Year. I’d buy myself a GC and then use it when people paid cash then keep recharging the GC and accumulate all the extra $5 coupons. I literally spent $0 total dollars on the GC but would get around $1000 coupons every year.

#48

When I park at the hospital I put the parking ticket thing in the machine to pay when I arrive (you are supposed to do it when you leave) thus paying the smallest amount (actually zero since it thinks you went in by accident or something). So far it’s worked every time.

#49

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.

#50

Many cheap (under $10) items on Amazon qualify for “returnless returns”, meaning if you start a return for the item you are issued a refund and prompted that there is no need to actually return it.

#51

An ex colleague of mine lost his car parking ticket one day and discovered that the car park near our work he used charges you £5 if you lost your ticket; not in addition to what you would have paid, just £5. The daily rate to park there from 9am to 5pm was £9/£10 from memory.

After making this discovery, on the days he drove to the office, he would park there from 9 to 5, and when leaving, would tell the car park attendant he lost his ticket, and would only be charged £5 instead of the higher rate he would have otherwise paid for parking.

I never had the courage to do it!

#52

Worked in a bank who gave staff half price credit cards. Interest was 18% so my card charged 9%. Term deposits were paying 14%. I would take out a cash advance (no charges for staff) and put that money in a term deposit- getting 14% paying back credit card at 9%. Saved a ton of money.

#53

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.

#54

I used to live in NYC and would travel quite a bit. I had a car in the city (wouldn’t recommend) and me and my wife figured out it was cheaper to park in a neighborhood in Queens outside of JFK, walk over to the airport, and just get a parking ticket and pay it, then it would have been if we just parked at the airport for an extended amount of time.

#55

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.

#56

Back in the early 2000s, Seattle Apartment buildings also rented “parking”. You pay a month’s parking fee, make a deposit for a garage door opener and that’s it.
No tag whatsoever, either you had their garage door clicker or you didn’t.

I moved around a bit across the city so I would pay for parking for a month and just keep the clickers and forgoing the $30 or so for each remote. I figured there’s no way building managers will reprogram remotes for all their residents every six months. So I’d at least be able to keep parking for six months which will save me $400-600. Turns out they did not reprogram remotes … ever.

I stayed in Seattle for six years, and I had free secure parking in at least four neighbourhoods across the city.

#57

In college, I realized that if you returned a book to the library one minute before closing, they wouldn’t have time to check it back in until the next day, so it technically wouldn’t count as overdue. Saved myself a ton of late fees with that trick.

#58

In high school a couple of friends and i discovered that you could purchase prepaid sim cards with more balance on them than what they did cost, plus get an additional $7 in cashback for every sim card ordered. We extensively used this to fund our leauge of legends skin collections.

And even better, at some point the carrier blocked us from purchasing more sim cards, but the cashback site we used still counted the purchase attempt as valid and credited our accounts. After a few months and multiple hundred dollars for each of us, the cashback site fixed the loop hole. Nowadays most sites take months for cashback to be paid out. Probably rightfully so.

#59

GameStop used to have like a 10 day return policy on used games. So me and my roommate in college would buy used games, beat them and return them. Essentially we got to rent games for free. We did this for years until the company caught on and started marking receipts and keeping track.

#60

When I was in high school in the 70s, it cost a dime to make a local call. We found out if you put a nickel in the slot, and pressed the return coin button at the right time, the coin would be returned and we’d get a dial tone to make the call!

#61

A kid was put on probation with me because he figured out the tokens from the local arcade were recognized as quarters at a bank’s self-serve coin exchange machine.

#62

This one is an *old* old school low-tech one (we are talking 50 years ago): soda vending machines used to contain bottles loaded horizontally, with the cap facing out. There was a pawl-like piece of metal that would prevent the bottle from being removed until money was inserted (the bottle was wider behind the pawl).
 
Some smart aleck figured out that you could get a glass and a bottle opener and just pop off the cap and let the soda pour out into the glass.

#63

Back in the late 90s, when dialup internet was still the main thing, I created a company for myself over the summer as I wanted to learn to run my own business, and I just wanted to be official. Just odd jobs, yard work, cleaning, maintenance. Typical teenager skilled stuff.

I created a business internet account through Sprint I paid like $25/month for the dedicated line and internet with unlimited hours. I shut the business down at end of the summer heading back into my senior year. I abandoned it essentially. I unlinked my payments, but I never canceled the internet account. I kept using it and I just expected it to shut down one day because I no longer had a business account paying the bill and the business was shuttered.

I used that dialup internet account for the next 3 years til I abandoned it myself upgrading to DSL. What’s even crazier is I found I could have a friend login on that same account as me at same time as well and it would work. I never received any delinquent bills aside from thr very first one to the business address, a PO Box I had, saying I missed my payment, and only 1 time ever.

#64

Our wedding registry gives you something like a 20% discount on purchases for a period after the wedding.

They also let you ship your gifts at your own pace, so we waited until after the honeymoon to ship gifts.

When we returned from our honeymoon we found out we could just turn all of our gifts we got into registry cash and buy everything at a 20% discount.

So we had a nice chunk of money left over to buy other items.

#65

I found these neat things on my pants that keep my belt attached to my pants.

#66

My roommate after college worked at a large search engine and the company would give employees free ad space on the website if they wanted it so we made ads to sign up for Uber using our referral codes where we would get $20 per sign up. We basically rode (Uber) and ate (uber eats) for free for 1.5 years. I forget why we stopped but there was some reason it stopped working.

#67

Not really a loophole, but in the same vein as some of the other comments:

DeviantArt.com used to let you gift Core Membership, which made the site ad-free and gave you some other premium goodies. And for the holidays, they had a “buy one get one free” thing where if you gifted someone a month of Core, you’d get a month for yourself.

It was an easy gift for everyone in my community, and I got free membership too. Well, after about the 16th purchase, they blocked me from buying anything else on their site XD I pulled in over a year’s worth of membership for free, and all my friends got something that was pretty coveted for that time.

#68

Back before Spotify was a thing I used Pandora, but I was in college so I had to use the free version with ads.

My android at the time was a couple years old. Anytime an ad came on or I was out of skips & didn’t like the song, I could just gently tap my phone on something and it would skip the ad.

I discovered it one day when I was annoyed by an ad and set my phone down harder than usual.

It worked for like a year until I got a new phone. I still don’t know how.

#69

In high school civics class, the teacher would ask current events questions. Then, at the end, he would ask a couple today in history questions. I found out that he got those questions out of the local newspaper EVERY day. I would memorize the answers and get them all right. Got tons on bonus points, and everyone thought I was a history buff.

#70

In highschool I had a physics test and we were allowed to use the internet on our laptops for it. We were told beforehand to still study as all the answer were in the text book.
So in my free period I searched for a place that wasn’t blocked by the schools firewall where I could make my own website, once I found one I went home, got my physics textbook CD, uploaded it to my computer and made my own website with all the diagrams and information needed onto my own website.

When we did the test, the teacher was monitoring what we were looking at and after the class pulled me aside and just simply said that he thought about stopping me from using the website but admired the thought I put in, advised me to remove everything to avoid getting in trouble in regards to copyright and that next year he’s going to make sure that others aren’t allowed to do what I did.

#71

In D&D 5e, you can use a lance one-handed so long as you’re mounted. And if you take the Dual Wielder feat, you can dual wield any weapons that aren’t two-handed. Since lances are weird, they do not have the “two-handed” property, nor do they count as “heavy” weapons. You can dual-wield lances. It’s fun.

#72

Not really a loophole, more if semi-unethical life tip.

Back in the late 90’s early 00’s I went to Vegas 3-4 times. I’m from Canada and back then I carried Traveler’s Cheques. The were Visa branded and in Candian currency. They looked identical to the US currency cheques, except the they said “CAN” under the denomination instead of “US”.

I went to a cash cage at a casino and cashed one of my cheques, and instead of converting it to US funds, they gave them to me at par! At the time $1 CAN would get you about $0.77 US!

Went back an hour later did it again and I got US funds, then she said “wait” that’s a CAN cheque. Took the US funds back did the conversion, and I got the lesser amount.

But I found I had about a 75% success rate with cash tellers not paying attention!

#73

When I had a Tesla – the garage at my apt building decided to jack up prices, but only start charging after the first 4 hours.

As long as I remembered to do it, I would unhook the charger and rehook right before the 4 hour mark. Had a full year of almost entirely free fuel.

#74

In college I discovered that if I had a balance of less than $10 on my credit card for more than a month they would do a SBW (Small balance wipe out). So every two months for years I used the card for something less than $10.

#75

Used to be able to get cheap flights on easyJet. this doesn’t work anymore so I can share it freely. we kept it secret for a while to try and not raise any alarms over there.

basically with the flexi fare you could change departure AND destination within the same price range, and you could change dates for each route.

meaning you’d pick a random flight that was cheap on selected dates and expensive in others. move it to those dates, and then choose another flight in that price range but which you could change the dates for even more expensive..

repeat until you can get the flight you need. regularly for 300 euros flights for 20.. very useful especially to travel around the holidays.

#76

I charged a hotel room to the wrong credit card once, so called customer service to get it refunded and recharged.

Over the phone, they process the refund and then connect you to the hotel to rebook. But the hotel couldn’t process my card for some reason, so I told them to forget it and I’ll just keep the original payment

But refunds are processed by main office, so I was refunded and never recharged by the property

About 2 years later, they were rechecking the books and ended up recharging me. But I called them and played dumb, and they cancelled the payment.

Worked once, but I never tried it again.