We all wish that we could find a loophole in life. Something that gave us an advantage or makes our lives a little easier. Well, some people do. And some of them are truly amazing. From money making schemes to free food, these writers found ways to game the system and get themselves a little something extra. Some aren't the most ethical, so we certainly aren't suggesting you do it. Please note some stories have been edited for clarity.

Intern Power
Intern Power

"This is a loophole that made me a ton of cash one semester.

In the late 1980s I was an intern at Apple. They had just released the Mac II - the first color Mac - and the machines were basically impossible to get.

As an intern, I was eligible for what Apple called 'first discount' - buying a machine at a substantial savings. I forget exactly what the savings was, but it was about 50–70% off. So the $8000 machine would only cost about $3k. AND we could get it immediately. The only catch is that everyone only got ONE first discount, so we had to use it wisely. If you bought something now, you would never get another in the future.

I wasn’t planning on getting one since I already had a machine provided by work and I didn’t have the money anyway. But then a family friend who owned a small business asked if there was any way I could get a machine since his local store had no availability. I told him I could buy it with my first discount and explained how it worked. He was super appreciative and paid me the full price for the machine. WAY more than my discount. I was a broke college student at the time, so I didn’t put up more than token resistance. He didn’t mind paying it, saying it was the price he would pay in a store, and this way he got it much sooner, and besides, he wanted to compensate me for giving up my discount.

So - all well and good so far.

A few weeks later, as the intern season was coming to an end, he contacted me again, asking if I could get another machine somehow. I tell him I only had that once discount but I would ask around. I asked some of my roommates and fellow interns and explained the situation, and someone let me use their discount as well. When I got paid, I split the extra cash with this person. I had a few thousand dollars for doing basically nothing.

At that point, the floodgates opened.

I systematically went down the list of all the interns, finding people who were not using their first discount and would be willing to give it up. I offered them $500. Many people were happy to take it. Meanwhile, I got a list of 'clients' who were willing to pay OVER market price for the machines in order to get them quickly. I focused on customers who wanted the highest end possible so the price (and my discount) was maxed out. These were also the hardest machines to get, so people would gladly pay a premium for quick delivery. I moved about a dozen machines before the list was tapped out. It took about a two months.

That was 30 years ago now, so I assume Apple has closed that loophole by now. Too bad, it was great while it lasted!"

Exploiting Bad Service
Exploiting Bad Service

"Has anyone ever exploited Domino’s?

I have. Twice.

Without any regret.

Going for it again? Absolutely.

It all started with wanting to eat a cheese burst pizza one day, my cousin and I were literally starving. We decided to order through Zomato because I had some pending credits. It was a rainy day and almost 9:30 PM, however Domino’s are open till 11, so we were sure about receiving the pizza within an hour.

After 45 mins when there were no updates from the restaurant, we pinged the Zomato chat support who apologized with a machine generated message and asked us to wait further. Finally, at 10:30 I lost my patience when there were no communications at all. The chat support then gave me 70 Zomato credits as compensation, which obviously is no consolation. The food showed up at 10:50, COLD! Cheese was hard. Thankfully the microwave saved the day. Doused with sauce, oregano and chili the Pizza tasted good finally.

We then talked to the Domino’s delivery guy, and he promised us a pizza the next day for free as it was closing time for them (11 P.M.) Meanwhile, I escalated this issue to Zomato, and they finally agreed to give me a refund, because Domino’s simply wouldn’t pick their calls.

The next day we called the restaurant but again they didn’t pick up the calls, but I had saved the delivery guy’s number and contacted the restaurant through him to get our free pizza.

And, at the end of the day, a refund plus 70 Zomato credits.

By this time we figured, this particular outlet’s number was wrongly listed. Or that they don’t use this number. And that they are routinely late on rainy days.

We pulled off another stint a few days later when it rained.

Ordered a pizza at 7 P.M to make sure we give enough time for the pizza to be delivered right by dinner time.

No news from them till 9 P.M. Didn’t pick up calls.

We got our pizza by 9:30 P.M.(which is a perfect dinner time as calculated).

Repeated the same with Zomato.

This time we got 150 Zomato credits, a refund and a free pizza the next day from the outlet.

Had Zomato taken their complaints sincerely or Domino’s made an attempt to rectify their services, we wouldn’t have landed gold."

Nightmare School
Nightmare School

"My high school has this stupid practice. If you're not sitting down by 7:30 each morning, you get booked in as late. Even if you've chosen to put your bag down before sitting and the bell strikes, they still hand you a pink slip.

Whoever’s late gotta stand in front of the parade square and sing the national anthem in front of the school. Talk about public humiliation. After the anthem’s over, they get hustled into the canteen to do Corrective Work Order (CWO). Their phones or wallet is then confiscated, and will only be returned after they completed detention that ends at 7 pm.

Talk about one nightmare of a school.

As usual, detention-ers aren't allowed to do homework or read a book. They're to stare at the walls for 4 hours straight.

One random morning, I had overslept and arrived at my school at 8:05 sharp. I expected myself to be doing CWO and detention, so I sighed and registered myself on the latecomer’s book.

Surprise, surprise. I was allowed to enter class like I wasn't late. Plus I hadn't missed much since my teachers were usually late.

No CWO, no detentions, no real consequences.

The school had serious under-staffing issues, so they couldn't always have 1 teacher at the gate waiting for late students to come.

I carried on the day as normal. I see my ‘law-abiding’ classmates who chose to run at 69 miles/h only to be slapped with detention clearly unhappy, grumbling under their breaths about how unfair this school is.

Well, I was like one of them. But not after that one random morning that I accidentally discovered the loophole.

Guess what this one a genius started to do? Come in a half-hour late every day. Because my school has this half-hour of assembly and my actual classes started at 8, I never missed a single actual lesson.

Also, my supposed ‘lateness’ was marked at present. Jokes on the system, they only consider attendance at first lessons due to people coming for morning assembly and skipping the rest of the school day.

Rather than listening to the principal rambling on and on about how terrible the school is, I spent my extra 1 hour actually being more productive than my 7 hours in school. Don't expose me, but I sometimes use that hour to start studying for tests that were on the same day."

Cheating For Charity
Cheating For Charity

"I used to work as a cashier at an expensive local organic grocery store and every so often they'd do 2 week-long charity drives where we'd have to ask people to donate with their purchase.

To incentivize the cashiers to actively participate in asking for donations, the management made it a contest. Whoever got the most donations during the drive, won a $50 gift card.

19 year old me was incredibly broke and determined to get that $50 and I mean, there's no harm in working harder to get charitable donations, right? That's what I told myself anyway.

Donation process:The cashier would type in a specific code for that charity drive followed by the amount the person wanted to donate, and it would be added to their purchase. Sometimes people would want to donate after they'd already paid, or they'd realize they had extra coins they could donate, etc, so people could also donate without making a purchase. This is where my loophole comes in.

Turning a charitable drive into a contest was management’s first mistake, not thinking through the contest’s design was their second.

They had designed the contest so that the winner would be the cashier with the most total donations to their register, not the person with the largest total amount donated. I thought that was incredibly annoying at first (shouldn't the goal be to get the highest amount of money donated?), until I realized I could exploit it. Many of the cashiers had been there for a long time and had regular customers that liked them and wanted to support the charity through that specific cashier, so I'd usually get customers who were less involved with the store and just wanted to get in and out.

Our typical script was 'would you like to make a donation of $5 to [charity]?', which I often heard 'no' in response to (which was an astral-plane leaving experience considering those same customers were the ones spending $35 on a bag of organic grapes but I digress). So, I started asking every customer to donate $1, and noticed that it instantly changed the amount of donations I received. Before someone donated I could usually figure out which customers would donate a higher amount and those who wouldn't want to donate at all. The second group was my target. If I determined someone to be a 'tough sell/donate,' I'd ask for 25cents. There aren't a lot of people proud enough to say no to giving up 25cents (but they do exist, believe me). That's a semi legal loophole, but then I found another one that was absolutely breaking the contest rules no doubt.

Sometimes, if people paid in cash, I'd ask if they wanted to leave the change behind to donate. Remember how I said there didn't have to be a purchase for there to be a donation entered and paid for? Well, when people left their change behind and left, I'd keep it all in a separate part of my register. During the times we weren't busy, I'd enter a small donation amount into the register, and then split up the change left behind to pay for each donation. For example, someone buys cookies for $3.47, pays $4 and decides to leave the $.53 to donate. I'd enter a donation for $.20, pay for it, throw away the receipt. Another donation for $.20 and a third for $.13, pay for em, throw away the receipts… effectively turning that one donation into three.

Unfortunately there's no exciting end to this story. I won, but another cashier caught me doing it the last day and ratted me out, so they gave the gift card to someone else. I totally deserved that, obviously…"

Ruined It For Himself
Ruined It For Himself

"I once saw one of my customers do something absolutely genius when I worked as a lowly till grunt at Sainsbury's.

So what did this customer do? Walk up to my till with a basket of shopping, followed by a whole tray of Avocados; I reckon about 30 of them, which I dutifully scanned, slightly bemused.

Perhaps they just really love making guacamole? I thought.

These particular Avocados were nearly out of date so were heavily discounted from £1.00 to 10p each. A pair of Avocados was now a bargain at 20p.

Now, it turns out our Avocados were also on offer. Not a great offer, just buy 2, save 50p. However, the till system was apparently dumb and didn't take into account reductions before applying this discount.

This customer clearly knew that bug existed.

So those bargain Avocados looked even more delicious when the 50p discount made them cost -30p a pair…

I stared in amusement as the -30p discounts rolled in and their shopping bill became smaller and smaller and smaller, until everything they bought was essentially free. They walked out of there smiling and I sat there, pondering just how dumb the checkout software writers were at Sainsbury's.

Nevertheless, sometime later I emailed management and told them what I'd seen. Later that year I tried the same thing, but alas, it seems they had discovered the bug and fixed it…

Oh well, at least those guys got free shopping.

All I got was a load of squishy Avocados…"

Wasn't Technically Illegal
Wasn't Technically Illegal

"When I was 18 I made approximately $11,000, 0.2 pence at a time, from an online bookie without placing a single bet.

The site in question was Coral and was one that I used fairly regularly to have a little flutter on the football and if I was really bored, or a bit tipsy, would sometimes play a few hands of blackjack.

Now these two areas of the site operated in different currencies. The sports betting side was in Pounds and the casino side was in Euros. When you made a deposit it went into your sports account and if you wanted to use it in the casino side they would convert it into Euros at the current exchange rate.

Well one day I noticed that there was no minimum amount that you could transfer and a question popped into my head.

How will the system work if I transferred a single cent from the casino side to the sports side? At the time one cent would be worth approximately 0.8 pence.

So I tried it and found out that it gave me a single penny. Now that might not seem like much but in effect I’d been paid 0.2 pence for that action.

This led me to the great money making scheme.

I started off with £200 available to me which I deposited onto the site and immediately moved over to the casino side which resulted in it being converted to approximately €240.

Then through the use of multiple instances of the site and an extremely long and complicated macro I was requesting the transfer of a single cent into my sports betting account at a rate of around 5 requests per second. When each conversion is giving me a profit of 0.2 pence that was giving me a penny a second profit. Once I’d converted all the Euros to Pounds I’d simply have it convert the entire lot back into Euros and start the whole process again. Doesn’t sound like much but that’s £36 profit per hour from something that’s simply running itself on a laptop sitting on the corner of my desk.

I had this running 24/7 for nearly two weeks. Now and then I’d stop it running to withdraw my profits before starting it back up again.

Eventually they did catch on. From memory, it took them 13 days before they noticed and I found my account permanently banned. Surprisingly I was able to keep all the money. I did receive a few aggressive emails from them, was threatened with legal action, however the fact of the matter was that there was absolutely nothing in any of their terms & conditions that prohibited what I had done, and so I walked away scot-free.

So that ladies and gentlemen is the story of how I made $11,000, 0.2 pence at a time."


"How a group of nerds got a restaurant to change their policy.

2011, Palo Alto, California

A group of hungry students frequented an Indian buffet restaurant near the Stanford campus. Why? Because the owner also allowed takeout at his buffet, so we could get one and split it among two. Back then we were poor graduate students with not enough money to afford to eat out much.

The restaurant had a sign that read 'All you can take in a box'

This is when a group of nerdy engineers decided to try to get creative.

Step 1:
We started filling the take out container with only one specific kind of curry. For example, 2 of us would go and start packing one container full of only butter chicken and the one full of only palak paneer. We also started optimizing the pieces to curry ratio. We would then go back home and eat this with frozen chapatis and fresh rice.
This improved our throughput from two people per box to three.

Step 2:
The next step of the master plan was pure genius. Nowhere did it say the box needs to be closed. So we started filling in a curry in each half of the box and grinning at the owner as we paid. He was a very friendly Punjabi man and while he was probably annoyed at the exploit, he took it in good spirit and commended us on the innovation and with a warm smile said it was ok and that he understood that we were hungry students just trying to save a few bucks.
This improved our throughput from two people per box to six.

Step 3:
Computer Science nerds have an obsession with optimization and naturally we wanted to live up to the reputation. So this final step was the pinnacle of our creativity and it’s probably the one thing that we will always remember. We realized that we were being limited in the amount of curry we could take out by the depth of the box. So we lined the entire box with quartered naans from the buffet to allow us significantly more volume and completely filled up our 'bowls' with curries.
This improved our throughput from two people per box to ten.

The next time we went to the restaurant, the sign had been changed. It now read:
'All you can take in a CLOSED box.'

Uncle just stood there and grinned when he saw our faces and walked off LIKE A BOSS which we stood there shocked at just how easily he had outwitted us. When we came up to pay that day, I couldn’t help look at him with the utmost respect and say 'Well played Uncle, Well played!."

Take That BOA
Take That BOA

"I was 17, about to turn 18 the next month. I knew I needed to start building credit, but given my only income was about 12 hours/week at $8/hour, not many places were keen on giving me a credit card much less without a co-signer (and I did not want a co-signer since it was my credit so my problem).

I finally found a credit card through Bank of America (my current bank too) that had about a $300 limit. Cool, I finally have a credit card!

As I was grabbing my paperwork and about to leave, the teller says,

'Hold on! I forgot to tell you one thing about this card!'

'Yes?' I answered hesitantly. I had already gone through the wringer looking for a card that I can qualify for, and the last thing I needed was another caveat.

'Your card has a cash-back feature as a promotion!' the teller beamed. 'That means if you spend $1.95, we will round up the purchase to $2. $1.95 will go to the purchase, and $0.05 will go into your savings.'

'Okay,' I think, 'it’s a way to get people to save more money. But how is this a promotion?'

'And,' the teller continued, 'Bank of America will match those funds transferred to your savings account 100% for the first three months of owning the card!'

Whoops, wrong thing to say to a very ambitious 17-year-old.

I immediately began scheming of ways to exploit this. Heck, I figured all I had to do was change my buying habits. The issue was, what do I purchase that I can really exploit this?

Then it hit me: I can buy gas.

Instead of filling up I would put $1.01 into my tank multiple times. Then Bank of America would match the $0.99 cents transferred to my savings account. Sure, it was tedious, but doing this for an hour I would make way more than when I worked at my actual job.

In the end I wasn’t as disciplined with this method as I would have liked. Frankly I felt very suspicious standing at the gas pump for half an hour.

I wound up making around $150 using this 'exploit' (I use quotations because if a 17-year-old can outsmart Bank of America, it had to be designed with this sort of use in mind.).

The funniest moment was when I told the teller at the bank what I had done at the end of the three months. She was not impressed. "

The Power Of Coffee
The Power Of Coffee

"About 4 years ago Dunkin’ Donuts did this promotion where if you signed up for DD Perks App you would get a free drink any size. Signing up for DD Perks meant downloading the app and signing up with your email. They wanted you to load up some money on the app to pay with so that you could earn rewards, but you got the free drink without doing this. So my friends and I every morning before class we would grab out free drinks. How were we able to do this every morning? Well, we would prep on the way there and make a whole new email account on our phones to use for the DD Perks App. It was super easy to do, you just typed in a user name, a password, and a phone number. Took about 2 minutes so then all we had to do was log out of the DD app and log back in with our new email and then BAM coupon for free coffee any size right on our screen.

It was pretty funny because eventually it felt like we ran out of email addresses. This worked for about a whole 2 years! Until they caught on. But they still couldn't stop us

So they eventually changed it so that now you HAD to load up money on the DD App in order to get the free drink. Well thanks, Dunkin Donuts! Because there was only a minimum of $2 that had to be loaded. Which was less than the cost of a small coffee. So what we did now, using the same email technique, was just load up the price of a Medium or Large drink using our debit cards to pay for the drink that day, and then use the coupon for the free drink the next day! Essentially, it was buy one get one free, as long as you knew how to swap out the email logins.

This worked for about another year until…. dun dun dunnnn……

They wouldn’t let you use the same debit card to load up the money on different accounts after about 10 times !

I did this for so long that when I had to replace my debit card and started it all over, I was only able to use it to load up money on different accounts a few times before I’d get an error on my screen that they were having 'technical difficulties.' Lies! You’re JUST now having technical difficulties when I finally have this figured out! I realized it was the system catching on to me, because I would put in my boyfriends card on that account and it would work just fine. For a few times…

So we let our thieving ways rest for a bit, maybe 2 months or so, until I decided to give it a try again. I was addicted. Probably something I was almost proud of? Jeez.

So I log onto the app again and the NERVE that Dunkin Donuts had!!

The raised the minimum amount of money you had to put on the app to -


TEN DOLLARS? That’s a free drink per 4 coffees! Lame lame lame.

I guess everything has its time though. I’m surprised it had made it those 3ish years. I did my best to keep the whole thing a secret so that it lived a long life.

On the bright side though, the death of the DD Perks Free Drink Loophole brought life to the ability to Online Ordering through the app. Which is great in the mornings when the line has literally (and I mean literally) made it into the street.

So I gain the ability to skip the line through the app, and walk away from my 3-year crime a free woman. No complaints here. I’ll continue to run on Dunkin’."

Ice Cream Genius
Ice Cream Genius

"One time I went to the mall and stopped by my favorite ice cream booth. I never really liked the idea of two scoops of ice cream — it just seemed like a waste of an extra dollar since it’s harder to eat and it can get pretty messy. But I saw that two of my favorite flavors were available: mint chip and bubblegum. I didn’t want to pay for two individual scoops, so I came up with an ingenious idea to get both. I went up to the counter and asked for half mint chip, half bubblegum. The counter lady looked kind of confused, but then proceeded to scoop up two scoops of the different flavors. At the checkout counter they had no choice but to charge me with the price of one scoop. I honestly didn’t know what I was expecting, and it turned out way better than I imagined (I thought they would just tell me that they couldn’t do that, but instead they gave me two 'half' scoops for the price of one).

This trick works because there is no way to scoop up a half scoop. The ice cream spoon thing can only scoop up a full scoop. So you will just end up with two full scoops of different flavors. And they can’t turn down your suggestion: half-half seems like an innocent request, and they can’t charge you with two scoops. I have used this trick at every single ice cream place I’ve visited, and it has worked every single time. So yeah, the trick to get two scoops of ice cream in different flavors for the price of one is to ask for half this, half that. Go on, my children, but remember — with great power comes great responsibility."

Technically Illegal
Technically Illegal

"Well, Starbucks have these membership cards that you can purchase for about $5.

These cards aren't SUPER useful at first glance. It's putting your money on a card that can ONLY be used to buy coffee, after all. Why do that when you can just use actual money?

Well, there's more to it then meets the eye for us cheapskates.

You see, being a member and getting your own card means that you get a free drink once a year for your birthday. And you don't have to show your birth certificate for them to determine your birthday. You simply fill out all that information when you first buy the card.

Because you can't just change the information once you've uploaded it, people think, 'Hey, why not just get a free coffee every year?'

For people like me, we want more.

Now, this is technically illegal, but if one HYPOTHETICALLY bought 365 cards, and set a different birthdate for each of them — one for each day of the year, of course — then they could get a free coffee.

Every day. For the rest of their life.

And before you tell me that it’s unethical and morally wrong, think of how good coffee is."

A Budding Doctor
A Budding Doctor

"I was accepted to Harvard Medical School without all the prerequisites and without taking the MCAT.

It was the fall of my junior year at MIT. I was studying/hanging out with a girl I had a crush on (a senior) and she was upset that her MCAT scores were not good enough. I was flipping through the brochure for Harvard Medical School, and saw what I thought might be a major loophole. I told her not to give them the MCAT scores, as they were not really an admissions' requirement. Of course, she didn’t believe me, and challenged me to apply and see if that 'loophole' worked.

So I did.

I sent in my application on the very last day applications were accepted, despite being a junior and not having all the prerequisites, finishing my application at 4am after studying for a couple exams and doing a problem set or two.

Not surprisingly, a few weeks later I received a letter from the Dean of Admissions for Harvard Medical School, informing me that there was no record of me having taken the MCATs, so unless their information was incorrect, they would have to withdraw my application.

I called up the admissions' office, and after several tries was finally able to speak to the Dean:

Dean Paul, I received a letter telling me that you would have to withdraw my application because I haven’t taken the MCAT.

I understand. Is that incorrect; have you taken the MCAT?

No, I haven’t.

Well, then I’m sorry, but we will have to withdraw your application; the MCAT is an admission requirement for Harvard Medical School.

With all due respect sir, I beg to differ. The MCAT is not an admission requirement for Harvard Medical School.

Wait, you’re telling me, the Dean of Admissions, what the admission requirements are?

Yes sir; I believe you are referring to the paragraph on page 29 that lists the entrance requirements for Harvard Medical School, and includes the MCAT on that list.

Yes, exactly.

Well, it clearly states that the MCAT is an entrance requirement; it doesn’t state that the MCAT is an admission requirement. So if you admit me in April, I will gladly take the MCAT over the summer and have it for you by the time I enter in September.

Ah, I don’t think that’s what it means.

I realize it may not be what you intended, but I’ve checked with two of my linguistics professors, including a Nobel prize winner, and they agree that is what the paragraph means.

Hmmm. Well, I’ll talk to the members of the committee and get back to you.

A couple of days later he called me back and told me that the committee had discussed the matter, and that while it was not what they intended, they agreed that it did indeed mean just that, so they would not withdraw my application.

At first I was very pleased, then I realized was that all that meant was that they were not going to officially withdraw my application, but they could still just unofficially withdraw it; i.e. ignore it and reject me, so I really didn’t think about it much, until I got a call to come in for an interview (that’s a whole different story!).

April rolled around, and a thick envelope arrived with my acceptance letter. Then a couple of weeks later I received another letter reminding me that I had not yet fulfilled all the entrance requirements, including the English and Biology requirements and the MCAT, and asking me to let them know when I would fulfill these.

Of course, the next year the language in the brochure was changed to close this loophole!"