D&D (2024) Creating good stealth rules for 2024 5e

Why don't we try and figure out how to make real world game situations work, to see if the rules make sense.

A sneaky PC needs to infiltrate a keep in order to ferret put some information. It is a moonlit night and one sleepy guard stands in front of the only unlocked access, while 2 more alert guards walk separate, opposite loops around the keep roof with any eye toward the ground. There are spots of cover, from a hay pile to lean-to stable.

The PC starts at a light woodbine 60 feet from the keep.

What are some action declarations the player can make in an attempt to gain entry,and what rules for stealth and perception would come to bear to adjudicate them?
I look for other access points. If there is no map, am i taking the DMs word for it that there aren't any or did we already scout? What kind of building only has 1 entry and exit way?
 

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Note the last check you made as per the rules. If you need to change position to not be found, (which happens all the time in movies), make a check to move to a new cover when the guard is distracted (maybe a distraction you create).
Ok, but what about the initial check? Is there one? Or should the "first one" be made when you move to cover for the first time?

In other words, borrowing from your own post:
I still think the action should only be required if you try to move from cover to cover or to set an ambush.
If we remove the initial "from cover" clause, the first check is made when you move to cover. You keep that result until you move to a new covered position, at which point that is now your check.

Under "routine" circumstances, the DM could allow passive Stealth to be used, perhaps only calling for a check when any passive Perceptions would automatically beat the passive Stealth.
 



What tools do i have at my disposal? Where is this keep? Is there a town around it? Outbuildings? Do you perchance have a....map?!?!? 🤓
 

I look for other access points. If there is no map, am i taking the DMs word for it that there aren't any or did we already scout? What kind of building only has 1 entry and exit way?

What kind of cover is around the outside of the building and how far is it from the sight of the guards?

How big is the building and how high up are the guys on the roof?

What level and class am I?

What tools do i have at my disposal? Where is this keep? Is there a town around it? Outbuildings? Do you perchance have a....map?!?!? 🤓

You are a 3rd level Rogue (Thief). The keep is 3 levels (30 feet tall) and 50 feet to a side. There is a main double door but it is barred. There is a servant's entrance on the opposite (rear) wall where the guard on the ground stands. The guards above can see the base of the keep. 60 feet from the keep on all sides is a light wood (light concealment) and it is moonlit (dim light). Assume there is total cover within 20 feet of any other total cover, but none closer than 30 feet from the keep.
 

Ok, but what about the initial check? Is there one? Or should the "first one" be made when you move to cover for the first time?

In other words, borrowing from your own post:

If we remove the initial "from cover" clause, the first check is made when you move to cover. You keep that result until you move to a new covered position, at which point that is now your check.

Under "routine" circumstances, the DM could allow passive Stealth to be used, perhaps only calling for a check when any passive Perceptions would automatically beat the passive Stealth.
This is a good point. Upon approach you automatically succeed at your Stealth roll to take a position anywhere along the wooded perimeter (your choice). You will have to make a new Stealth check once you do something.
 

Are these mercenaries or knights guarding the keep? Why am I trying to get inside? What time is it? How long has the guy at the door been on shift? What’s my alignment? What brings us here?

This is a fun exercise but there are variable involved that this “not map” style of play doesn’t work for me.

This doesn’t seem like a stealth situation. I would more likely try brute force or just lie my way in. Possibly bribe or pretend I’m someone else. Possibly create a diversion of some kind. You can’t sneak past people who are looking at you.
 

You are a 3rd level Rogue (Thief). The keep is 3 levels (30 feet tall) and 50 feet to a side. There is a main double door but it is barred. There is a servant's entrance on the opposite (rear) wall where the guard on the ground stands. The guards above can see the base of the keep. 60 feet from the keep on all sides is a light wood (light concealment) and it is moonlit (dim light). Assume there is total cover within 20 feet of any other total cover, but none closer than 30 feet from the keep.
Playing along, my plan would be climb the walls and sneak into the keep from the top. Climb speed and BA Dash means I could get from the closest area of cover to the top of the wall while still having my action which is probably a Dash to get off the roof and into the keep, or failing that to find cover on the roof so that next turn I could get into the keep from the rooftop.

But since that's not super fun, how about this, time my approach to the keep to avoid the guards looking my way and just get right up against the wall, ideally on the side that is shadowed so that even though the moon is generally providing dim light inside the shadow it would be actual darkness. Wait there hidden in the shadows expecting that even though it is possible to be seen by the patrolling guards if they have darkvision or a torch, it's still fairly unlikely. Note this is definitely an area where player/dm assumptions might clash, since my assumption is the guards would be focused on looking at the fields so by being right up against the wall I would actually be out of the vision cone unless they stuck their heads over the side and looked straight down.

Once the patrol passed I would then climb the wall and find somewhere out of the guards sightlines which shouldn't be too hard given they are looking outside so even without cover, if I'm quiet and quick enough I can get to whatever door leads into the keep itself.
 

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