Alright, this is a long post but I promise it goes somewhere.
Back when I was working for an alphabet soup agency, there was this one time when I was in charge of an asset transfer. We were to fly to a remote airfield in Kazakhstan to meet the asset's handlers, collect the asset and fly back to the US. You have to understand that this was a strictly confidential operation, our asset was on the run from a pretty big guy and had to be collected ASAP for his safety.
When we arrived at the point of exchange, it turned out that the asset's handlers had three extra prisoners (bound and in hoods) with them that they were willing to let go free of charge. I initially refused to take them with us (it could potentially compromise the safety of the transfer), but they convinced me after the handlers stated that the extra prisoners were working for the big guy that our asset was on the run from, and therefore might have valuable info on him. With that in mind I couldn't resist taking them along; I was very career-minded back then and always looking for a feather in my cap, so to speak. I told my associates to get the men on board and called Langley to report the change of plans per normal procedure.
After we were underway, I attempted to get valuable info out the prisoners by calling their bluff in a classic interrogation technique. I told the three men that the flight plan only listed one of them in addition to me, my associates, and the asset. The first one to talk would be thrown out of the plane after being shot in the head (none of this would actually happen, they would be hauled off to the back of the plane after the interrogation). Remember, the prisoners were wearing hoods, so they wouldn't know what was actually going on.
I opened one of the plane's side doors and had my men bring the prisoners over. I attempted to get information out of the first but he didn't talk, so I pretended to shoot him with my USP and throw him out of the plane. I brought the second prisoner up to the door, but he wouldn't talk either. I pointed out that these prisoners had a lot of loyalty for their boss, especially considering the fact that they were likely just hired thugs with no reason to remain devoted to their boss. It was then that the third prisoner spoke, pointing out that they probably knew that I was trying to call their bluff, seeing as how there really wasn't any reason to shoot a man when he was going to be thrown out of a plane seconds later anyway.
It was in that moment that I decided to take off the third prisoner's hood to get a better look at the guy. To my surprise, the third prisoner was the guy that our asset was on the run from! What luck! I decided to begin interrogating him immediately. He was very cooperative, and disclosed to me that he intentionally allowed himself to get caught so he could get on board the prisoner transfer and ascertain the amount of intel the asset had revealed to us about him (we hadn't debriefed the asset yet, so he hadn't told us anything of substance). The asset was visibly disturbed by the big guy's presence, and exclaimed that he had told us nothing.
It was about here that I began to feel uneasy, though I'm not sure why. I was still firmly in control of the situation and if the guy tried anything, we had him outnumbered. I got a little cocky with the guy and suddenly, he broke out of his handcuffs and started beating the shit out of me. Bullets started flying, and the plane got tilted nose-first, causing me to fall down the passenger cabin and onto the pilot cabin's door. My last thoughts before I blacked out were that the situation was completely surreal, and that I had no idea what was happening or how I had lost control of the situation so quickly.
I woke up hours later on some desolate steppes, surrounded by wreckage from my plane. I would later learn that the big guy used a larger plane to take control of our own plane and grab our asset from us. The fact that he now had the asset would have extreme consequences, but at that moment I had bigger problems to deal with. I had to hike across the rugged terrain, bruised, bloodied and beaten, so I could contact my superiors and tell them what had transpired.
TL; DR: When I was doing government work overseas, I took a chance on grabbing extra prisoners and it backfired spectacularly. We didn't fly so good.