Loopholes are rare, but they happen. And when they do, you better believe you’re going to take advantage of them. Why not, right? Not your fault there’s some kind of glitch that lets you make easy money or increase the convenience of something!

In a recent Reddit thread, people share the best loophole they’ve ever come across and how they exploited the heck out of them. We can’t say we blame them!

  1. Internet Minutes

    Was on a cruise ship a few years ago that had a pay-per-minute Internet policy. You’d buy like 200 minutes of wifi access for $100 or whatever crazy price it was. They had a little portal that you went to, to start and stop the timer, and tell you how much time was remaining. I quickly realized that the timer counted by whole minutes. That is, if I started at 12:00:01, and stopped it at 12:00:58, then it counted as 0 minutes of internet use. For the entire cruise I took advantage of this. Start the timer, fire up your internet apps like Facebook and Instagram and let your timeline and emails download, or launch a website and let it load. Stop the timer. Browse your feed and photos and read your website and emails offline, compose posts and replies etc. Start the timer again to send/upload, stop it again within a minute. I milked those 200 minutes for an entire 3 week cruise and still had 45 minutes left over at the end.”

  2. 100% Retirement Match

    “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.”

  3. Unlimited PTO

    “I worked at a place where you could request any day off with pay according to what you had accrued. We would ask for a day off with pay and then work our regular scheduled day off. 6 days paid. Work 5. Anything over 40 was OT.”

  4. Movie Rewards

    “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.”

  5. Parking Garage Fees

    “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.”

  6. Crane Game Wins

    “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!”

  7. A Ton of Tickets

    “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.”

  8. Free Pizza

    “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.”

  9. Phone Promos

    “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). I really miss this type of promotion!!”

  10. TV Rewards

    “Early in the smartphone world there was an app that gave you points for watching TV shows and ads that you could turn in for gift cards or discount codes. The rewards were not great but over time and by waiting for gift card restock you could make out like a bandit. However, the shows they wanted you to watch were not my cup of tea (a lot of prime time shows and reality shows) and I wasn’t home for a lot of them so I thought I was SOL. Turns out, the app had a grace period where if you had recorded the show on your TV you could still get credit, so I just pirated the shows and set my phone up to “watch” them while I did something else. Then I realized it only listened for about 2 minutes before it gave you credit so I was able to get through the log of shows in about 40 minutes and make a killing. Because of that app I was able to get a kitchen aid stand mixer, a smoker and a bunch of other stuff because of the gift cards.”

  11. Soda Machine Glitch

    “The soda machine at a dorm I lived in had a weird glitch. If you put in five cents more than the asking price and pushed the product select button, the machine would empty all of its change out at once. We did this a few times and got $20-40 each time!”

  12. A Bloody Good Cause

    “Had intermittent anemia in college that I was trying to improve. But the blood work was about $100 each time. I started donating blood and if I was too low they’d turn me away and I’d keep trying to up my iron. If I was high enough, I got to donate to a good cause. Win win!”

  13. A $1 Dresser

    “I once bought a gorgeous, solid oak dresser with attached mirror accent that was priced at $1200 for only $1. I was on a website surfing for dressers for my newborn and came across a free shipping promotion. So I filtered results for dressers for the lowest priced item. Up pops this dresser for only $1. Upon further inspection I realized that the same dresser in other finishes were priced correctly at $1200. But this oak dresser was priced in error. I reluctantly added to my cart half expecting it to update the price… but it remained $1. Plus they had free shipping that day, so my cart total was $1.06. I completed the transaction and then called their CS number. I explained and was put on hold for almost 20 minutes. The woman came back and confirmed it was an error but that they had to honor the price. The page it was on went unavailable before I could let anyone else in on my find…freight shipping was also normally $399 so it was a truly an amazing score.”

Have you ever found a loophole like one of these?