I'm not saying my mother didn't like me, but she kept looking for loopholes in my birth certificate.

-Les Dawson.

This article is a collection of the best answers from a Reddit thread in which user Ninjalord5 asked the question, "What was a loophole that you found and exploited the hell out of?" A big thank you goes out to all the contributors.

1. I worked in a call center during college. Our main performance measure was the number of donations solicited PER CONTACT. If the person didn't answer or hung up immediately, it didn't count against you.

I discovered a bug where, if I blew into the microphone just as the phone started to ring, it would register in the computer system as a no-answer and dial the next number. I rode this out for several months before I got tired of blowing my microphone for 8 hours a day and quit.
smokebreak

2. Back in college we found a loophole with coupons at Kroger for General Mills cereal. If you bought 4 boxes of cereal each box was a dollar. But if you did the self checkout you would be printed out a coupon for $4 off your next purchase. We used the loophole to buy about 300 boxes of cereal. We only spent $12 on all of it. We would've spent less but we had to go to another Kroger once the manager got wind of us. We kept around 20 boxes for ourselves and donated the rest to the local food bank. They were so excited when we showed up with three vehicles full of cereal. Totally worth the $12 and all the time it took.
RoiVampire

3. Worked in a call center.

I discovered my cubicle block was not hooked up to the call quality monitoring, so I would just answer calls, put them on hold, then call the same 1-800 number they dialed to get me and conference call it with them. Then I would sit there silently listening to some other poor shmuck handle the call and would drop off the call around 7 minutes which was our preferred average handle time. Got told my call time was great by the boss a few times.

My coworkers and I called it call surfing. Sometimes I would interject with words like "Penis" just to see how confused both parties would get.
Smooth_McDouglette

4. Bought a shitty sega genesis game, I think it was some flight sim which was the crappiest game I ever played. So I took it back to K-mart and got told "No refunds for opened games. Replacement for the same one if broken." Annoyed that I couldn't get my money back I said it was broken and went for the replacement. They handed me a new copy of the game and my original receipt.

Left and came back an hour later, "I want a refund for this game, here is my receipt and unopened game." Got my money back, went and bought a different shit genesis game.
FOTBWN

5. In elementary school we had the Accelerated Reading (AR) program. You would read a book, take a test on the computer, and be awarded points based on how well you did. At the end of the year you could buy things at the book store with the points you accumulated.

I had just finished reading Harry Potter and the Prisoner of Azkaban and got a perfect score on the test. The computer was only supposed to allow you to take the test once but I figured out you could take that specific Harry Potter book unlimited times. I racked up so many points and was never found out.
saucecat2

6. I used to go to MS events at my college because they gave away free shrink-wrapped software, which I would then sell on ebay.

AnthonyGonzalez27780

7. At my local movie theater, you could get a small drink for $2.50 or a large drink for $3.50, and large gets unlimited refills. Or you could get a SoBe tea for $2.50. But they didn't give you the SoBe bottle because they wanted to avoid any broken glass incidents. So they poured the SoBe into the large cup. Boom: unlimited large drink refills.

I saved several dollars that way.
r2d2sthirdleg

8. By accident I found a gumball machine that, if you turned the dial really slowly, would drop the gumball. Then you could dial it back just enough so the next gumball would drop into the tumbler bits, then slowly dial forward again until it drops, etc. Got about 20 of them and stopped when I realized that I really didn't want to chew that much cheap gum...
Kifenstein

9. In the 80's Chuck E Cheeses didn't shred the tickets you get out of their games and use to buy toys, candy etc. My friends and I were biking one day behind a strip mall practicing our wheelies and jumps. We saw a worker throwing a garbage bag of tickets into the dumpster behind Chuck E Cheese. We grabbed it and then started circling back about once a week. Garbage bags and garbage bags full of tickets. We were doing so well, one of my friends parents got in on it. She would take the mini van behind there and have her kids load up. And this is why tickets are now shredded.

10. I think I still have a huge stockpile of Frisbees and stuffed animals in my parent's attic somewhere.
bboy1977

11. My college didn't put any dates on our Student IDs. No graduation year, no expiration date, nothing. As a result, I kept using it to get student discounts for YEARS after I graduated, mostly the 15% off J. Crew discount.

hummingbird4289