There’s a difference between gaming the system (exploiting a loophole) and actually breaking the law and getting away with it
The question asks for a gaming method, not break the law and cheat

Seb Paquet

I give you… The Pudding Hack:

1. In 1999, UC-Davis civil engineer David Phillips was grocery shopping when he noticed something peculiar. Healthy Choice Foods was offering frequent-flyer miles to customers who bought its products. But a 25-cent pudding would bring 100 miles — the reward was worth more than the product itself.
2. Recognizing a good thing, Phillips bought 12,150 servings of pudding for $3,140, claiming he was stocking up for Y2K. Then he enlisted the Salvation Army to help him peel off the UPC codes, in exchange for donating the pudding.
3. He mailed his submission to Healthy Choice, and to their credit they awarded him 1.25 million frequent-flyer miles, enough for 31 round trips to Europe, 42 to Hawaii, 21 to Australia, or 50 anywhere in the United States.
4. There’s no downside. Phillips also got AAdvantage Gold status for life with American Airlines, which brings a special reservations number, priority boarding, upgrades, and bonus miles. And he got an $815 tax writeoff for donating the pudding.

Alex Leach

Here’s a good one! US employee ‘outsourced job to China’
Outsource your entire job

1. A security check on a US company has reportedly revealed one of its staff was outsourcing his work to China.
2. The software developer, in his 40s, is thought to have spent his workdays surfing the web, watching cat videos on YouTube and browsing Reddit and eBay.
3. He reportedly paid just a fifth of his six-figure salary to a company based in Shenyang to do his job.

Shashank M Chanmal

This one is absolutely brilliant:

In Mumbai, there is a group that runs an “insurance” service for ticket-less travel on local trains. This is a real beauty. Considering that there are millions of passengers being transported every day, the statistical chances of one being caught is very slim. This is how this works : you pay a very small fee to the gang each month, this is about 1/10th the going rate for a monthly railway pass. You never buy a ticket but keep traveling blithely in the trains. If you get caught, don’t argue. Pay the fine, come to your “agent,” hand over the receipt and get reimbursed. Everyone wins, except the Indian Railways of course.

Vishnu Rajamanickam

The Ingenious ATM Swindle

This was a clever idea by which crores of rupees (amounts to about one million dollars) were swindled from ATM machines across India by tricksters. The methodology involved was very simple and it revolved around a simple flaw in the system : That the ATM would withdraw the money that rolls out after a few seconds if the person does not take it out. The technique involved withdrawing money from the machine, taking out a part of the currency notes it throws up and letting the machine swallow the rest. Since the machine cannot count the retracted notes, some banks credit back the entire amount to the account.

So if a customer withdraws Rs 10,000, pockets Rs 9,000 and lets the machine retract Rs 1,000, some banks record the transaction as null and the entire Rs 10,000 remains in the account. Most ATMs are designed to retract the cash if the customer does not pull it out within 42 seconds.

Kerala-based Federal Bank had lost Rs 75 lakh to a Punjab gang that attacked its ATMs across the country using this method.

After this episode, ATMs across the country have been altered and these days the ATMs do not withdraw the money that it throws out.

Crores swindled from banks as fraudsters exploit design flaw in ATMs


This is from, whose writers always seem to be able to find the strangest examples I could never even dream of

In the late 1960s, Leonard Casley grew way too much wheat, which could only ever be a serious problem if you live in Australia. You see, Australia had wheat quotas at the time and Hutt River (the province where Casley and other families grew) had inadvertently surpassed it, meaning they weren’t allowed to sell any of it. When they petitioned for the quota to be raised, the governor responded by saying, “No,” and filing a law to take their land away. THAT’S how serious Australians are about wheat.

In a desperate attempt to delay the legal process, the five families of Hutt River seceded from Australia under the Treason Act of 1495. This would have been as pointless as that time you were five and told your mom you were leaving home… if the government hadn’t accidentally referred to Casley as “Administrator of Hutt River Province” in official correspondence, which actually gave him legal recognition as a ruler under Australian law. Yes, in Australia, calling someone something magically turns them into that.

Taking full of advantage of the mistake, Casley declared himself His Majesty Prince Leonard I of Hutt, meaning it was now treason, under Australian law, to charge him with any crime or interfere with how he ran his new country.

Could Australia have stopped him? Sure. But by the time they got around to it, the statute of limitations had run out. So as of 1972, The Principality of Hutt River had officially seceded from Australia and stopped paying income taxes.

As of the modern day, Hutt River is still separate, while Australia treats it as a private business that doesn’t pay them taxes and just tries, really hard, to pretend it’s not there.

See: wikipedia

Pranav Reddy

I was blessed with awesome people around me in college who loved to take advantage of the loopholes in the system.

1. In the early days of e-commerce in India, back in 2009, eBay used to give coupons of Rs.250 off when you create a new account. So you can get anything on eBay which costs less than Rs.250 for free. We made hundreds of mail ids and ordered stuff varying from notebooks to soaps and shampoo. After this experience, we wanted to improve the efficiency. We bought personal domains and started using google apps so that we get unlimited number of mail ids. Meanwhile, eBay realised that we were looting them and got the ‘Minimum Purchase’ condition in checkout.
2. And then in my sophomore year of college came into news Google Wave. Yes, Google Wave. I’m not sure if Google would have made money on that. But we did. By selling the invites. It was “invite only” based for the first one or two weeks. And each one who’s already in it would get to send 50 invites. Two of us had the invites and we multiplied the invites using our other mail ids and started selling them on eBay. We couldn’t believe it, when we saw people buying each invite for $20. Trust me, when you convert $20 into Indian currency, it was pretty big money for us. The party lasted for a week and soon the price dipped to $0.99.
3. Another one was out of a referral program for a well known web hosting site (ends with a “Gator”). A friend of mine would get $100 if someone with his referral hosts his website with that hosting service for three months. The cost of it for three months would be $30. I used to host my website for three months paying $30 and we divided the $70 profit.
4. And in junior (third) year of college, we had a small event of our Electronics school. The number of people expected were around 200. We mailed an “online recharge” website (say “Free”…), which was in its initial stages of getting popular, for sponsorship. They weren’t ready to give money, but sent us McDonald’s, Barista, Pizza Hut coupons (which they give to people who recharge on their website) worth Rs.100000. We were shocked. Distributed as many coupons as possible and even gave them to people walking around in the campus. The event was a huge success. No one even knew what was happening, but it was colorful with people around talking about free coupons. Even after all, we were left with hundreds of McDonalds coupons. Then it started. The “McD Loot” as we fondly call it. In McD, during the peak hours, they had a policy which says that if they don’t serve the order in 60 seconds, the customer would get a free coke. One or two careful observations and we figured out that a certain item on the menu would take more than a minute for sure. It was Filet-O-Fish. We’d go and pay with the coupon for Filet-O-Fish. It’d take at least 70-80 seconds even if they stopped every other order and served us. We’d then ask for a free Coke and finish our meal for free. This happened so many times that after two months, in that online recharge website, they mentioned that the McD coupons aren’t valid anymore in my city. And also they removed the “Free Coke” policy. I’m not sure if it was a coincidence, but a week later, when we actually paid and had food for the first time in months, we won a cricket kit (worth Rs.4k) in McSpicy Burger launch contest.
5. And coming to the final blast which left everyone speechless, it was a survey of an American cable company (ends with a word which also means a group of performers in a play or a movie). The survey was taken by a third party which promised Amazon gift vouchers of $5 for every survey. And they were so dumb that the survey url, in which by changing the random 6 digits at the end, it will let you do another survey. So, after each survey, we get a 16 digit Amazon gift code of $5. And also that the credentials of the survey taker would NOT in any case be given to other third party (as mentioned before taking it). In one day, we made around $8000 all together. Ordered tablets, phones, and what not. Every other thing we dreamt of, from Amazon.

These were the prominent ones. It’s not always about money, but that excitement you get out of pointing wrong in something which is considered to be sealproof. Ahh… Makes you feel like being on top of the world.

Aravind Bharadwaj

A $1 bill costs the mint a lot more than a $1 coin in the long run.The US mint wanted to increase the circulation of the $1 coin and started offering rolls of it that people could buy online using their credit cards – without any caps on how much an individual can buy.

Jane Liaw Liaw is one of the many people who cheated the system.

Here’s how one could cheat the system:

1. Order coins from the mint using your frequent flyer/cash back credit card
2. Receive the coins (shipped free)
3. Deposit the coins in your bank account
4. Pay off the credit card statement balance
5. Keep the frequent flyer points/cash back that the credit card gives you

Jane went on several international trips free of charge using these miles. Other people who took advantage of the system did similar fun things by exploiting the loophole they found.

The mint has now closed the loophole by limiting the number of coins that can be ordered per person per period of time Source:npr

Gil Eyal

A friend of mine used to have many Pen Pals when we were younger. At some point he started to send letters without a stamp, by writing the intended recipient’s address as the sender’s address, and his own as the intended recipient. The letters would then be delivered to the real intended recipient because the post office thought the recipient was the sender who forgot to put a stamp.

Mohit Saluja

This happened in 2002.

Two young boys, 18 years old, in New Jersey took an ad out in the New York Post. They said they were selling the top 10 x-rated videos for 49.95$. These videos normally sell for 100$ apiece. So one time offer, 49.95$, all 10 videos original version, uncut. But no cash, no credit cards, cheque or money order only. So a lot of people went and got a money order, got a cheque and mailed it to this P.O. box in New Jersey.

The kids took the cheque and legally deposited it into a bank account. They had opened a small business account. Then they wrote you a letter the next day back on a very nice letterhead that said “Thank you very much for your order. Unfortunately, due to the huge demand we are unable to fill it so please find enclosed a cheque for 49.95$ to cover your full refund.

It was a real cheque. It was a legitimate account that had the money in it to cover for it. The only problem was that the name of the company was printed in the top left hand corner of the cheque and it was done in fire engine red in big block letters and the name of the company was CHILD PORNOGRAPHY VIDEOS INCORPORATED. So nobody cashed the cheque and the kids kept all the 49.95′s. Source: Interviews By Spencer – Frank Abagnale – 4/05 ctrl+f 49.95 to reach the spot.

via Quora