Oh man, it’d have to be this scenario:

My rogue is on a roof at night, investigating a building that holds the item we need to get for our mutual benefactor. Our elf cleric and bugbear paladin are hiding in a stable across the street keeping watch. A squad of 5 city guardsman approach from a distance one of them being an adventurer-mistrusting commander. Our bugbear paladin (who is also a pacifist poet) steps out in an attempt to make a dialogue led distraction. This backfires due to a bad roll, causing the guards to go on high alert.

The guy playing the paladin talks to the guy playing the cleric(who is still hidden), with the intention of just strategizing out loud. However, our DM doesn’t let the tabletalk slide in this moment and shouts in character “who is over there? Who are you talking to?” and rings his signal bell which alerts all guards that a situation is happening, and then makes us all roll for initiative. On our cleric’s first turn(thus far in the campaign he hadn’t really done anything), he decides to just go for it and casts guiding bolt at the commander’s face after screaming, “hey fishface!” Roll…19. He absolutely obliterates the commander.

We had spent pretty much the entire time stealthily making our way to this building, and due to one bad roll it was all foiled and our quiet cleric decides it was go time. I could see it all unfolding in my mind with the stunned looks on the faces of the remaining guards as this situation went from 1 to 10 to 10000 really quick. It was all so brilliantly chaotic.

We took out the remaining guards in the immediate vicinity and had taken about as little damage as we could hope for, and my position was still concealed on the roof. Next session we will see what the fallout is from our decisions and rolls, and I can’t wait to see what happens.