"I worked as a 'ghost passenger' for an airline. Basically, I flew around and graded flight attendants' performance. While still parked at the gate with the door open, one flight attendant began berating passengers who were using their smart phones, which was completely permitted at the gate. She threatened to have the person in front of me thrown off the plane if she didn't put hers away. She also threatened me.
After we left the gate and were taxiing to the runway, I looked back to see her sitting in her jump seat. using her phone. I took a photo of it and included it in my report. She initially denied using the phone and claimed I was being unruly on the aircraft. After she saw the photo, she changed her tune."
"I do social engineering for financial institutions (banks, credit unions, etc). I went to a credit union in Texas which failed on a miserable basis for security. I walked in with a fake badge that stated I worked for a made up company and that I was there to do an inspection of the building. I dressed in a polo and khaki pants with matching colors to my badge and walked in to the front desk.
The girl there was probably in college or just out of school. She immediately let me into the back room and I walked into offices and desks that were unoccupied but located in rooms with other employees. I walked up to empty computers in use and plugged in USB drives. Huge no no. I began typing random things into computers and taking pictures of myself at the computers. Employees would literally look at me and go back to their jobs without thinking anything of a guy taking selfies at their friend's work desk.
Once I had been in every office, I went to the vice president's office. I opened her desk and looked through files to find people's personal information. I found tons. I went into the file room and took personal loan documents off the shelf and took pictures of myself accessing them. When I was done, I walked to the person who had contracted my company and laid out all the information I had found and all the things I had done. The guy just sighed. This scenario has happened a couple of different times. Most places fail somehow."
"I used to own a game store at which we bought and sold Magic: The Gathering cards in Maryland. There was a big tournament in Pittsburgh the weekend before at which someone's collection (worth a few thousand dollars) was stolen. That day, we were visited by someone we had never seen in the store before looking to sell a collection - a collection matching the description of the stolen collection.
I told him that we were interested, but needed to set up a longer time to sit down and look through the collection. We set up a time for the following Tuesday and they went on their way. We then called the police in Pittsburgh who connected us with a detective. He worked with our local county police and they set up a sting. There were three cops in the store pretending to play (one of whom actually knew how and is now a regular) and two more in unmarked cars outside.
When the guy came into the store, I did exactly what I would have done with a regular collection. I rung it up, negotiated, and paid the guy for the collection. Once the money exchanged hands, the cops busted him. Collection was returned to the kid in Pittsburgh and the guy ended up with some plea deal involving probation."
"I worked for an armored car service for a while as an undercover guard. When a place had a lot of money or if it was a risky area, two plainclothes guards would arrive before the truck. I would scout the place and the outside area to make sure the uniformed guys could get in and out safe. We wore a color of the day and the local cops knew who we were as did the uniformed guards.
It was a pretty easy job and I only once waved off a pickup because of a bunch of Latin kings sitting on benches out front. I hung out a while to see what was going on and hoping they would leave so we could make the pickup. As I sat on a bus bench across the road I watched one of the guys closely, and I couldn’t believe what he took out of his pocket.