RPGMemes

I did a one-shot once with a Bethesda start (locked in a prison with a bunch of stranger) pickpocketed the keys off the guard, got caught, convinced the guard to gift me the keys, then when the guard saw me giving the keys to another player I convinced the guard I was just passing on the kindness. I then snuck into the office of the warden (boss) stole some magical items (including an immovable rod). Later after the inevitable fight where the other players who actually had the stats to fight wasted a few guards, I did successfully convince a couple of guards to just go home for the day before I snuck out.

Later attempting to escape through the city, we're stopped by some guards who'd heard about the prison escape and see a rag-tag group covered in blood and in a hurry so they assume we're the escaped prisoners. I told them we were midwives leaving a very messy birth and heading to another emergency (advantage on that roll was all that caused it to land) then ultimately met up with the warden at the town gate who I simply trapped with my immovable rod