“I worked at a restaurant in a hotel where you could collect “employee bucks” of sorts for going above and beyond at your job. You could use them to pay for things like a room stay or food in the hotel restaurant. They were worth a dollar each, but you obviously couldn’t cash them in for real money. I saved up about $450 worth, used $100 worth to pay for a hotel room on a day I was working, bought a soda from myself at the restaurant and tipped myself the extra ~$350 and signed it all to my room bill. Upon checkout it just shows that I spent $350 at the restaurant, not a breakdown of the bill. So then I used my employee bucks to pay off the hotel bill and got an extra $350 on my paycheck (minus taxes of course).”

“Domino’s pizza Australia. When ordering online, delivery charge was added to the first pizza. So I’d buy garlic bread, hot chips, chicken wings, a drink and some deserts and skip the delivery fee by paying by card online. Kept it up for 2 years before they “updated their terms” and shut the loophole.”

“Moviepass was $10 a month and you could use it to get 1 movie ticket a day. I lived next door to a Regal, and I went everyday because Regal would give their reward points for every ticket purchased. They didn’t care that Moviepass was paying for the tickets then giving them to me as part of my subscription. In 8 months I spent $80 on the subscription and saw everything that came out and I racked up enough Regal rewards points for about 50 free popcorns or drinks. Moviepass went out of business but I still had all the Regal rewards.”

“In college there was a parking garage that charged around $2/hour. I couldn’t get a parking pass but learned the heated garage that charged $2/hour had a $20 fee for a lost ticket. I would park my car in there for a few weeks at a time and when I had to leave would lose my ticket and be forced to pay the $20 lost ticket fee. ​ A parking pass was around $500 to park outside and I ended up paying around $300 in lost ticket fees to park in the heated garage.”

“When my brothers and I were 6-10 years old we found a crane candy game where you were “guaranteed to win” something. We found a laser sensor in the area where you pick up your prize. This indicated whether or not something had dropped. So, by holding the flap door open at the bottom the sensor was never triggered so for 25 cents we nearly emptied the machine. Thanks Red Robin!”

“Right out of college I worked a job that had a 100% match to any retirement contributions. I was young, lived rent free with my parents, Had no student debt, and could grab OT nearly every week. After some budgeting I figured I could throw 80% of my paycheck into retirement. I did so for 9 months until my supervisor called me into the office to sign a policy change that limited retirement contributions to 50%. I’d stashed away nearly $35,000 on about a ~$32,000 annual pay. I had no life for about a year, but damn if it didn’t jump start my retirement.”

“When I was at university, the pay-for campus printers all worked on a system where you’d print your documents, release them at the printer, they’d print, then after they’ve finished printing, it would then contact the server to get the cost deducted from your balance. That final step always took a while and I discovered in my first year that if I cancelled the print job as the final page was rolling out of the printer, it wouldn’t deduct the cost from my balance. With this method I got free printing for nearly two years before they upgraded the system!”

“I bought a card once for $10 that had 16 coupons for a BOGO pizza from Dominos. They were little stickers that you were supposed to pull off and hand in when using them, but they never asked for the stickers. They also didn’t have an expiration on them. They also didn’t tell anyone it was supposed to be one per order. We’d order 8 pizzas at a time, used them for two years. Thousands of dollars of free pizza really help when you’re a broke college kid.”

“Several years ago AT&T was running a trade-in promotion increasing the value of old iPhones way beyond what they were selling for on eBay/ CL at the time. This promo thankfully wasn’t bundled to a new phone purchase and could be done on any active line of service with AT&T – so no limits on phone trade-ins."

“I ended up buying 31 old iPhone 4s for about $70 each on eBay and trading them all in to AT&T on promotion for $200. Worked out to $6200 in AT&T credits (got myself 2 iPads, a 2 new iPhones at the time, and enough of a credit on my bill I didn’t pay for cell phone service for almost 2 years).”

“Not sure if it counts as a loophole, but I worked at a books/music/video store when I was in high school. We were supposed to remove the “in training” portion of our name tags after the first two weeks. I just left mine on so that customers wouldn’t ask me questions. A full year of hardly anyone talking to me at work was the best full year of my life.”

“I remember being young and going to Chuck E. Cheese. When you were pulling your tickets out, if you found this sweet spot then you could just keep pulling the tickets out. My mom had a hard time figuring out how I got 10,000 tickets in under an hour.”

“I lived near a casino that would let you get chips using your credit card. I liked some of the shows and restaurants there but never gambled. So every time I went I’d charge $5K to my credit card for chips. Then I’d cash out at a different teller swing by the bank on the way home deposit the money and pay off my credit card. I did this maybe once a week. Boom $5K of free points / cash back.”

“The local Wendy's had a survey on the back of their receipt that would get you one free burger of your choice with the purchase of any other “premium” burger. They also had a special on where the Dave’s classic single, considered a premium burger, was $2. The first time I didn’t even make a purchase, just went into the store, found a receipt near the garbage, filled out the survey, got my code, and then ordered their Asiago cheese chicken burger (their most expensive item) with a Dave’s Single. 2 burgers for $2.”

‘1 Credit Card point for every dollar spent. But up to 5X for every dollar spent abroad. I’ve been on a 6 year “holiday” abroad and they haven’t brought it up.”