I knew a guy in college who would use his foodstamps to buy the expensive milk with a deposit on the glass bottle it came in. He would pour the milk down the drain in the parking lot and return the glass bottles for cash. Super f****d up and unethical, but it was a loophole and he exploited the F**k out of it for beer money.

Back when you could win a free coke under the bottle cap, I spotted a pattern where the caps that I won had a logo on the top that looked faded, whereas the losers all looked pristine. For 2 weeks, everyday after school I'd stop at the UDF and exchange yesterday's cap for a new coke.

I made tens of thousands of dollars by creating accounts at online casinos, getting "new customer" bonuses, gambling a small amount, and then cashing out.

Back when Hollywood Video was around, they would guarantee new releases to be in stock. If they rented out all of their copies in the store then they would give you a voucher for a free rental. I was in college at the time and would go into the store near my college campus at around 10pm on a Friday night. There was simply no way for them to have any copies left by that time, so I would collect whichever vouchers were available. Rinse, repeat. Cheaper than redbox.

I always bring an old starbucks cup to starbucks and ask for a refill. They always give me a new cup and since I have a "gold" card, its free.

My '96 Jeep Cherokee used to leak transmission fluid really badly. Luckily, Jiffy Lube offered free "top-offs" on all fluids between oil changes. So I would just pull into Jiffy Lube every couple of weeks and have them fill my transmission fluid back up. They did not like me.

Not truly a loophole, but I got a flier in the mail one day from a pizza joint advertising 5 dollar large pizzas on certain days of the week with a code that was valid for another month. I'm still using the code to this day, three years later. It's only worked at the local branch so far, but I've been riding that gravy train as hard as possible.

Back in the 80s. Raffle for a car had write your own entries. Printed off thousands of pages of entries on my printer. Won car. Unfortunately I was too young to drive. My sister totaled it before I got my license.

There used to be an electronics store called 'Hastings' where I grew up that sold both new and used electronics. They had a deal that if you traded in 3 used games of a common type (e.g. all ps2 games) you could get a brand new game for free, no strings attached, just free, any game of that system. So I would go into the store buy 3 incredibly cheap used games (bass pro hunting or whatever it was called for 5$, they had dozens) and then walk out, double back, and then trade those in for a $60 brand new game. I did this constantly for a few months while being harrassed by the managers there until they stopped the promotion.

There's these 3 Dunkin Donuts in my area that let you buy "Coffee Cards" basically you pay 200$ for the card and can come through any part of the day, how ever much you want a day and get an any size coffee for a year. Well my mom bought one last year and it had expired; she bought another one this year and it looks EXACTLY THE SAME as the old one; They took no effort into changing the card at all, so my mom gave me her old one and I get free coffee whenever I want.

I was in Costa Rica at a casino, losing money left and right on blackjack. I left the table and went to find my buddy, turns out he was playing casino poker, the kind where you play against the dealer. I had never been interested in it before but I was sick of losing at blackjack in Spanish so I sat down and bet. I was freaked out the first time it happened because I didn't think it was legal, but all 5 players at the table would compare the cards in their hands before the dealer turned over his. This way we knew if we had a shot at winning with a straight or flush, which paid more, or should fold. I don't know if the dealer cared or could not understand English, but we all cleaned up at that table over the course of an hour or so. I walked away with over a grand.

A long long time ago Hostess chips (was the major brand in Canada at the time) had a Mario Bros promo. You got a "bingo" card in each bag of chips and every card was a winner. You had to scratch 3 of 9 areas and if you matched the icons you won. One of my friends figured out that using a tin can with a tiny hole punched in the bottom and then dropped down unto a 100W lightbulb, you could see through the card and find the winning spots to scratch. This spread around town and a week later there wasn't a single bag of chips to be found anywhere. Sold out all over town. We all had garbage bags of open chips around. I won 1 grand prize which was a Super Mario Bros game.

There was a site where you could upload your own games and make revenue for every time someone visited the page. Turns out just refreshing the page counted as a visit, so I found an auto refresher and left it on 24/7. I made almost $2,000 before they figured out what was happening and now it only works from different IP addresses

Clipped ALL the Sunday "5 dollar off" coupons for the restaurant i waited tables at, every time someone payed cash, i got an extra 5 dollar tip. I made way too much money doing that.

This is the story of how I passed math and graduated from college. So my university was notoriously awful for their math program. They used MyMathLab and it was just generally s**t. I was terrible at math anyway. You had the option of testing out of classes. You would go to the testing center, pay five bucks and take a test. So this was my plan to get my math credits. I'd go take the test, find out what I got stuck on and then work on that type of problem until I understood how to do it. Then i'd go back, take the test again. So and and so forth. I probably took the test like 8 times in a semester. Finally I passed that f****r and got my math credit out of the way. The next semester a new rule was implemented that you could only try and test out of a class twice per semester.