A player picks a lot of fights with NPCs or otherwise does things that would trigger punishment normally. We’ll ignore hypothetical cases where this is due to interpersonal issues at the table and only deal with the case where the player knows there’s a consequence and is willing to take the risk. But how do you handle it?
I see jail in the game being like any other downtime activity, like training or enchanting items. The PC is inactive until the sentence is served, but other characters can attempt a rescue, and the player can suggest plans for escape, like winning over one of the guards or sneaking a message out to a retainer. Some scenarios can be played out to see if the plan works, but for the most part, that character is considered unavailable, and the player switches to a backup character.
It doesn’t actually have to be traumatic, or mean the end of the player’s participation. If the player is traumatized, though… well, that’s probably one of those interpersonal issues, then.
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