While it might seem like cheating, the truth is that loopholes in anything from game rules to laws exist only because someone didn’t do their due diligence. As they say, don’t hate the player, hate the game, so it can be entertaining and even illuminating at times to find out strategies netizens have used.
Someone asked “What was a loophole that you found and exploited the hell out of?” and people shared their best examples. So get comfortable as you scroll through, upvote your favorites and be sure to add your own thoughts and examples in the comments below.
#1
It was in Navy boot camp, and if you’ve ever been through boot camp you know that speaking during meals is forbidden. Not even a whisper.
Then service week arrived and the chain of command ordered me to work the mess hall. The job was to pass out cups at the beverage section in order to move the line as fast as possible.
Being on service week, I was permitted to talk. Used that loophole to smile and give each recruit their cup by name. “Here you go, Miller.” Read the names off their uniforms. It was the only time all day that somebody treated them like a human being.
The smiles of gratitude were priceless.

Image source: doublestitch, Getty Images
#2
Back in college I had a thirty day trial for some software. This was back in the early 2000s when that stuff wasn’t quite as sophisticated. I found that if I kept changing my computer calendar back before opening the program, it would think I was still within the initial month. I did this for years.

#3
There’s a Jack in the Box right near me. When you buy something, you get a link to a survey for three free tacos. When you get the tacos, they give you a new receipt with a new survey code.
Infinite Tacos.

Image source: digikun, Jeswin Thomas
#4
During the last year of University a couple of my friends and I discovered that one of the buildings often did like a fancy buffet table if it was hosting a lecture for visitors. It actually was quite a common occurrence and we realised that the people looking after the food didn’t care if you were part of the visitors or not so we would just go along and take a bunch of free food.
Great for poor and starving students!

Image source: PixelPoppah, engin akyurt
#5
Back in the day (2007/2008) I found a major flaw in the POS at Blockbuster
Their system would update overnight, but only certain parts, and these parts were on different days of the week. Their new item prices would update on Thursday, their used prices would update on Friday- BUT their trade-in values would update after closing on Sunday.
This meant if a game dropped in MSRP, it’s new version would first lower on Thursday morning ($49.99 to $19.99) and be cheaper than the used version. The next day, on Friday morning, it’s used version would be lowered ($47.99 to $17.99).
The trade-in value would still be the same- usually $30-$35, even though you could pull the game off the rack, buy it for $20, then trade in back without leaving the line.
I did this a few times and felt bad so I emailed corporate to let them know about the loophole. They told me they didn’t take in information/suggestions from outside parties, essentially because they had that set up as part of their “business strategy.”
I then proceeded to assist them in their endeavors by buying 25+ copies of Beowulf from Best Buy for $9.99 ($19.99-$10 coupon) and trading them in for ~$800 in store credit.
Then I repurchased all 25 copies with the store credit for ~$500.
Then I traded them in again.
Then I bought them again.
I did this a few times over the weekend and ended up with $1200 in store credit from $250 cash.
Then I found a few games GameStop gave good money for and traded them in over there for store credit. I made some preorder and eventually canceled them and requested cash back for the deposit.
I eventually got a letter from Blockbuster banning me from trading, but it had the wrong date (post dated for the next year) and I kept trading.
I don’t feel bad about it.
Image source: Ditypol
#6
My college didn’t put any dates on our Student IDs. No graduation year, no expiration date, nothing. As a result, I kept using it to get student discounts for YEARS after I graduated, mostly the 15% off J. Crew discount.

Image source: vabhj, RDNE Stock project
#7
My wife had foot surgery this summer. Daughter had a short hospital stay earlier this year. We’ve met our family insurance deductable so now that everything is covered at 100% everyone is stocking up on medical supplies, procedures, chiropractic visits, and anything else we normally can’t afford.

Image source: Runner40, Getty Images
#8
I was once the only person to show up to a Microsoft CRM event, since I was the only person to attend I automatically won the door prize of a Xbox 360 with a Kinect.
The downside of this loophole was 3 long hours of talking with MS product evangelists who were very disheartened and desperate to make a sale.

Image source: tonyjack123, Kamil Switalski
#9
My credit card through my bank gives me reward points. My card is linked to my checking account. You used to get points every time you used your checking account to pay a bill, as well as points for spending on the card. They originally didn’t put a limit on how many times you could pay a bill in a month and still get points. So I was literally paying my credit card bill after every single purchase. Coffee in the morning? Pay bill online. Lunch. Pay bill. Gasoline. Pay bill. Etc. I was getting more points from paying my bill over a hundred times a month than I was from using the card. They changed this after about 2 years.

Image source: yupyepyupyep, Getty Images
#10
Early on in Minecraft, if you dug a hole straight down, go into the corner, and used 3rd person to look in just the right direction, you could see through the block texture. the result was you could see things like caves and lava pits really easily, which was key to finding good ore back then.
We called it “Prospecting”. It was eventually patched out.

Image source: Razorray21, Zenithik
#11
Before they changed the machine, if you played Hungry Hungry Hippos alone at Chuckie Cheese you got all of the tickets that would normally go between 4 players, because obviously your hippo gets the most food. It really appealed to my “I don’t have any friends” side.

Image source: anon, Mike Mozart
#12
I had a coin operated washing machine and dryer in my college apartment. 4 quarters to wash, 8 quarters to dry. We figured out that if you opened the dryer with 1 minute left on the clock and inserted 1 additional quarter the timer would reset to max dry time. Laundry went from $3 to $1.25. Unfortunately the landlords daughter lived in the same complex and ratted us out and they replaced the dryer with a s***tier one.

Image source: danbert88, Oli Woodman
#13
Calling the FCC on Comcast because Comcast is a bag of d***s. Every time my bill gets lower, and I’ve even been flagged as a problem customer, but I keep calling with legitimate complaints (internet speed slower than I pay for; unnecessary fees attached to my bill; paying for an extra box when I only have 1).
My bill went down from $150/month to $60/month. Blazing fast internet and all of the premium channels. My goal is to have them paying me for their service by 2017 if given the chance.

Image source: anon, May Gauthier
#14
Most online news sources want to charge you after something like 10 articles. Easily avoidable if you either adjust your cookies to clear automatically, or browse in safe mode.
Image source: anon
#15
Lawyer here – Adobe has a loophole where, if someone uses their redaction program, you can open the pdf on an older computer that is slower, zoom in and out real fast and the redaction disappear.
I had a case where the defendant was a con man but good at what he did…so our securities violation case was really a toss-up – had to do with joint venture interest… anyway
Guy has to produce text messages – and some of which had redaction – I did my trick, found out the guy was dealing d***s as well – turned the f****r over for d**g trafficking (because he was selling Rx pills across state lines) and well, we lost the civil case, but f****d him over anyway.
Image source: bushidomonkofshadow
#16
Working in NYC they are constantly filming SOMETHING somewhere. I always noticed that there was usually a tent with a full spread of food and various people eating from it. Sometimes there was a food truck too. On a particularly hot day I popped my head in and grabbed a cold water. Nobody batted an eye. Ok, that was refreshing. About a month later they were filming for a few days in a row outside of my apartment. I finally got some balls one morning and walked in and grabbed a bagel and coffee. Nothing…….. The next day I did the same. A friendly smile and good morning was all I got from the guy putting scones out and cooking up some eggs. The next day I walked in during the morning and the “chef” was making omelettes. HE ASKED ME if I wanted an omelette. Who was I to turn down such a kind gesture. That was the last day they were filming by my apartment, but whenever I see a film crew I look for the tent and grab a little something.
Also, sorry for your $20 movie ticket.
Image source: Nachocheeze60
#17
Back in the 90s I figured out if you dialled 14711471 on a pay phone it gave you an open line without needing any money.
Free phone calls for me :D
Which was useful because I lived miles away from my friends and liked to chat to them for hours on the phone.

Image source: zenova360, Kateryna Hliznitsova
#18
Back in a computer class during grade school we had to use this test program for the class. We would learn how to use word, excel, etc then take the test. Well I figured out that during the test if you hit CTRL-A, it would highlight everything on the page, except for the correct multiple choice answer. Got an easy A in the class.

Image source: Burntmaybe, sunrise University
#19
When i was in college a guy actually bought a calculator ($30) from the bookstore and just pressed the buttons through the plastic packaging and returned it at the end of the semester.

Image source: anon, toml_12953
#20
EMT here. In our charting system, there is an entire menu of choices for a patient’s prescription medicines. I was always taught how to fill out this menu item by item (which, for older folks, can be incredibly tedious). One day, scrolling through the huge list of meds looking for one or another, I found the option: “List Given To ED Staff”. One click, and I don’t have to spend 10 minutes typing in medications. Sounds like a small thing, but boy does it make a difference.
Image source: Deerinthecamplight
#21
When I lived in my first apartment in college we only had 2 parking spaces but 3 of us had cars. I got my car 4 months after we signed the lease so I was the one with no parking pass. My complex was notorious for towing people without passes immediately. I had a geo prism (it’s an incredibly small car) and I eventually realized somehow that if I parked next to the dumpster the tow truck wouldn’t be able to tow me because it couldn’t fit back there, so that’s where I parked everyday for the rest of my lease and never had to pay for parking.
Image source: water_light_show
#22
I used to take this shortcut to work, through a rich neighborhood. Recently they put up a sign that says “No Right Turn Between 7am-10am” to ~~stop poor people from driving through~~ ease up traffic congestion.
However, if I drive past the street a ways, pull over, and then make a U-turn? Now I’m turning *left* onto the road. So it’s not illegal.
Image source: scorpionjacket
#23
ISPs and cable companies love to sign you up by offering new subscriber deals. problem is the rate ends after a time and you are paying a higher rate. and you are usually under contract so it costs you to get out of it…unless you move out of their service area.
So in college between years my roommates and i would systematically cancel our contracts saying we were moving, then another roommate called and started service under his name. we got the discount rates for 4 straight yearsw.

Image source: apleima2, Getty Images
#24
My last job I worked at for 5 years gave me discounts to a ton of things.
I stopped working there, but I never returned my employee card. I still a**se the hell out of it for free parking, free museums, free movie tickets, free subway rides, etc.

Image source: Isunova, Georgi Dyulgerov
#25
I downloaded a free trial of WinRAR. I found that if the trial runs out, you can still use the software. I’ve been using WinRAR for free for years! Life has never been better.

Image source: 2Sp00kyAndN0ped, Wesley Tingey
#26
The soda machine near the locker room. For some reason, every now and then, when you bought a Hawaiian Punch, the flood gates would open and all of the remaining HP’s would flood out.
Whenever I had some change I’d give it a shot. We had different theories about what made it work, but I think it was just random.

Image source: LaserBeamsCattleProd, Sab Wang
#27
Not me- back in around 2004 a friend of mine found out his bank couldn’t charge him fees while in his student overdraft, he also discovered the train company he uses took money sometimes 7 working days after the purchase. He’d buy a train ticket on the day with no money in his account, he’d get the train 3-7 days later the company would try and take the money, it wasn’t there and the bank couldn’t charge him fees. They sent letter after letter and he just kept doing it for years, never picking up his phone to the bank.
One day he goes into branch and the manager summoned him into the back office, explained that he had been manipulating a loop hole and the bank were having to pay for everyone of his train tickets. He shrugged and said I have no money to pay into the account that account will always be empty, just close it. Manager said they couldn’t close it w/out his permission. He asked how much his permission was worth.
£250 quid it was worth and a promise to please use another bank.
Have asked banking friends about this and that loophole is now well and truly closed sadly.

Image source: anon, Evelyn Liow
#28
Gatorade had an under-the-cap contest one summer (like 20 years ago). And they were still being sold in glass bottles. Well, the glass bottles of lemon ice – you could just flip the bottle over and read the cap without opening it. I must have looked at 500 bottles that Summer and won a bunch of c**p. A CD wallet and a pack of basketball cards were about the best things I won.
Image source: aspbergerinparadise
#29
I go to a lot of baseball games, but sometimes the lines are insane, especially for a giveaway.
I found out that if you enter the stadium from the gift shop the line is probably never more than 50 people deep, and you still get whatever the giveaway is.
I mean, some people line up for those giveaways HOURS before gates open.
Image source: crimesofparis513
#30
Papa John’s had an online coupon which could only be used once but by changing the URL you could print new coupons. Would take me 20 seconds to find an unused code and free pizza time. After about 10 free pizzas the manager called to ask how I was getting so many codes so I quit.

Image source: braaibros, Getty Images
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