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

I'm simply going to bring back the Hidden condition from the playtest. I don't have it right now, or I'd post it for those who don't have it. It worked fine IIRC, and the only real thing I see as an issue is that See Invisibility effects don't work on it (which I'm fine with).
 

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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.
I would call for 2 stealth checks to get to the keep : one to the first area of cover, then another to the keep. If the guards are going the opposite direction at the same rate, you would have 2 rounds with no guard looking down on your side.

The roof is tricky. There's no cover, but the guards' attention is focused outward, so I'd make it a wash for one more stealth check. The tricky part is what happens if you get to the hatch down and it is locked? In 2024, how long does it take to pick a lock?
 

In 2024, how long does it take to pick a lock?
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Stealth combines the old Thief abilities Hide in Shadows and Move Silently, so you don't have to make separate rolls. Though, it should be noted in 1E/2E that using Hide in Shadows required you to be still. That got dropped in 3E when those abilities were turned into skills (separate skills initially).
great thought
 


I would call for 2 stealth checks to get to the keep : one to the first area of cover, then another to the keep. If the guards are going the opposite direction at the same rate, you would have 2 rounds with no guard looking down on your side.

The roof is tricky. There's no cover, but the guards' attention is focused outward, so I'd make it a wash for one more stealth check. The tricky part is what happens if you get to the hatch down and it is locked? In 2024, how long does it take to pick a lock?
To me this would be an issue, too many rolls and failure becomes inevitable, I'm already at 4 skills checks including picking the lock, and no doubt have a bunch more skill checks ahead of me inside the keep. So unless you are treating these failures as something other then being seen then you're really discouraging using stealth which because it's D&D probably means taking the murder hobo approach.

And as an aside it seems very strange that the guards would be going in opposite directions, I would've though they would be taking the exact same route but halfway apart. And locking the door into the keep is also a very odd thing to do, it would logically slow down any reinforcements which is liability.
 


This has always been an issue IMO.
Yes which is why in someways having vaguely defined rules that are up to the DM to interpret has it's benefits. It's why the DMG advice on the subject should be about how the different interpretations/rulings impact the game so that DMs can rule in a way that produces the tone of game they want.
 



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