I used to work in a photo lab at a grocery store before the automated machines took over. I used to pretend to stock film, and stole over 50 rolls over a three or four month period. Developed and printed all of my pictures for free. labelled the envelopes "test roll #." No one found out.
Somewhat recently, one of my old roommates used to sell weed and made a deal with some dudes who worked overnight at a grocery store. We recruited two homies to help. We went in and filled four shopping carts to the top with groceries and beer, over four hundred dollars worth of stuff easily, in exchange for an eighth of weed. When the guys were "ringing us up," they put a paper towel over the sensor so that nothing would show up in the system. Problem was the evening supervisor was onto us and was standing maybe ten feet away watching the whole thing go down. The supervisor watched us pay $16 for four shopping carts worth of goods, and I was convinced that there would be police cars waiting outside the doors as soon as we bailed. Instead, the two grocery store workers got fired and we never saw them again. All for an eighth of weed.
It's funny, I remember looking around my apartment and thinking I had never seen a pantry so full of food before... but the food went too quickly, and soon after that I was unemployed and eating bags of popcorn for a month, so I think I learned my lesson.
I haven't stolen anything substantial since. I feel bad picking up spare change that i see lying around.