I think each character's hearing radius should be based on their passive perception. If the characters passive perception is 11, then there is a radius of 11 ft around the character. If you pass within that radius, you have to make a stealth roll against their passive perception. But I think it should go further than that. There should be a second hearing ring. This is a radius that is twice your passive perception. You still have to make a stealth roll if within the second ring, but you get advantage on your roll. If you're within a character's sight cone, you get disadvantage on your roll. Darkness of course provides advantage if in a person's sight cone.

What would this look like? Your character is wearing heavy armor and has disadvantage on stealth. However, they are sneaking around behind an enemy. They reach the outer hearing ring. They would have to make a stealth roll with neither advantage or disadvantage. Why? Because the disadvantage of the armor is negated by the advantage of sneaking around in the outer ring. One roll it's made. For the entire duration of you sneaking around in that outer ring, you don't have to roll again. As you sneak into the inner ring, a stealth roll must be made at disadvantage because the armor causes disadvantage and you are also in the inner hearing ring. So it's much harder for someone in heavy armor to sneak up that close.

Here's a rogue example, and the Rogue has expertise. The Rogue enters outer hearing ring. The Rogue has advantage on stealth. Rogue enters inner ring. The Rogue has a regular stealth check with no advantage or disadvantage. That Rogue is going to have a much better chance than the person in heavy armor to sneak up and backstab. The Rogue suddenly winds up in the characters sight cone. The road now has disadvantage. The rogue with expertise will still actually have a chance to succeed simply because their skill is so much better. Even with disadvantage they are so good at sneaking that they might still avoid being detected, especially in darkness which would negate the disadvantage.

Why one roll per hearing ring or site cone? Because players don't usually like it when they at first succeed but then the DM makes them roll again and they fail. If you succeed per ring or cone, you should be given at least some lenience so it's not super frustrating.

Last edited by GM4Him; 04/04/22 01:30 PM.