The rules detail that an encounter triggered in a room may make a Listen check against party members Move Silently to possibly prepare, against party members is within 20 feet of the door. We speed this up by only having the person within 20 feet with the worst modifier to Move Silently make this roll. It’s assumed that he will be loudest a majority of the time and the monsters only need to hear one person to know someone is attempting to come in the room.

Conversely, when wandering monsters appear, whether in battle or while exploring with no active encounters, we have the best modifier for Listen in the character group closest to the monster placement make a roll to see if the party is surprised.

Example: Syrath, the Rogue is up ahead, scouting and preparing to unlock a door. Meanwhile a random encounter is rolled and the monsters are placed behind the party, having come down from an unexplored hallway. The party member in the group closest to the monsters, with the highest modifier to Listen makes a roll against the monster’s Move Silently skill. If the monsters are successful, they are placed on the table at the furthest entry point from the party. If unsuccessful, the monsters are placed so that they are within melee range if they take a move action during the surprise round.

In this example, if the monsters were decided to have come from an unexplored hallway further into the dungeon, beyond Syrath, only he would be able to make the Listen check to avoid being surprised since he is the only group member in the “character group closest to monster placement.” 

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