D&D 5E Questions on stealth...

First and most important: The 5E stealth rules are a dumpster fire. It doesn't matter what the "official" word is. Ask your DM how s/he intends to rule on these questions, and build to that standard.

Now, as another DM, here's my interpretation of the written rules. The 5E SRD states that "you can't hide from a creature that can see you clearly" (emphasis mine). I don't have my PHB handy, but I believe the word "clearly" was added in errata post-release; if so, it dramatically changes the operation of the stealth rules, which formerly required total concealment. Because of things like the Skulker feat and the wood elf's ability to hide in nature, I would not rule that light obscurement (dim light or light mist) is sufficient to hide, but I would allow hiding in situations where you aren't completely unseen.

1) Invisible rogue enters antimagic zone: If the guards are not otherwise distracted and there is no concealment, the rogue is instantly spotted. Night or day, doesn't matter. They can see you clearly, so you can't hide. If you were making a point to stay behind cover even while invisible, and there was cover available, I'd give you a roll; but anyone setting up an antimagic zone to stop invisible intruders is likely to arrange it so there's nothing to hide behind.

If you have the Skulker feat, it's different. Skulker allows you to hide in areas of light obscurement. So if the lighting is poor (e.g., because it's night), you can remain hidden even when the AM field kicks in. Unlike the general stealth rules, this one is really not debatable - if your DM doesn't let you stay hidden in this situation, you should be allowed to exchange Skulker for a feat which has not been eviscerated by DM fiat.

2) Rogue hiding on edge of a roof and peering down: When you poke your head over the edge, you can be seen, but you can't necessarily be seen clearly. Therefore, I would allow hiding.
 
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Well I guess I absolutely have to take Skulker then, and ask my GM about differences between in combat stealth and out of combat. On that note, any idea how to deal with Alarm spells in place on doors and windows everywhere? Even for an arcane trickster Raw it's not til level 13 you get an answer to it, with dispel magic. The setting is fairly high magic. Tbh, I'm actually just thinking I might make my next stealth character a full blown wizard because it's easier than trying to make rogue work.

Edit: For informations sake these encounters were at level 9, and exp gains are slow so it'll be there for a while.
 

You can also become Hidden if you become Heavily Obscured. Dense foliage, opaque fog or smoke, or being in darkness all qualify as Heavily Obscured, which means you also can now make a DEX (Stealth) check to become Hidden as well.

I'm a bit confused with the Heavily Obscured condition. It basically says if you're heavily obscured, you are essentially blind. So why do you have to make a Dex check to become hidden if your opponent is blind? I can see it if you're making a lot of noise, but if you're hiding at the end of the hall and not doing anything, would you still need a Dex check?

Also, shouldn't range have some kind of impact on stealth? In dense foliage I might have zero chance of seeing someone several meters away, but I sure as heck can see the people standing beside me.
 
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I probably should add that I feel like your DM is putting the PCs in a no-win situation and then blaming them for losing. Rule #1 of DMing: If you don't want the PCs to solve every problem by kicking in the door and killing everything, give them a chance to solve problems in other ways. Stealth and infiltration are top of that list.

Anti-magic fields are a big deal. It takes a 15th-level wizard (!) to create even a temporary AM field. To make a permanent one and bind it to a location is an epic achievement in my book. It's the sort of thing you'd find in the defenses erected by an ancient empire around an Artifact of Doom, not something you set up to keep invisible riff-raff out of the palace. For that, you just hang a bead curtain in the doorway.
 

I probably should add that I feel like your DM is putting the PCs in a no-win situation and then blaming them for losing. Rule #1 of DMing: If you don't want the PCs to solve every problem by kicking in the door and killing everything, give them a chance to solve problems in other ways. Stealth and infiltration are top of that list.

Anti-magic fields are a big deal. It takes a 15th-level wizard (!) to create even a temporary AM field. To make a permanent one and bind it to a location is an epic achievement in my book. It's the sort of thing you'd find in the defenses erected by an ancient empire around an Artifact of Doom, not something you set up to keep invisible riff-raff out of the palace. For that, you just hang a bead curtain in the doorway.

Ugh. You know, I'd kinda felt the same way for a while but didn't want to go raising a stink and rules lawyering, but I guess I'll have to bring it up sooner or later. I already had the GM try to shut down using higher level spell slots to the boost the Life Cleric passive on healing spells. I actually had to rules lawyer that one cause what's the point of it otherwise? I would have lost 70% of my bonus healing under that interpretation. But yeah, the GM wants us not to murder everything so I'll have to try to talk about it.
 

On that note, any idea how to deal with Alarm spells in place on doors and windows everywhere?

(Expendable) minions (ideally fanatical and/or fabricated, but cold hard gold-bought and/or good 'ole coercion works in a pinch) and misdirection.

They can have as many alarms as they need - there's a finite number of guards (I would hope!) and when alarms start triggering all over the place there's only so many places the guards can be at one time.

Send the minions in to trigger the alarms, you waltz in during the chaos and nab the nabbables. Disguise yourself as a guard, servant or visiting dignitary just in case someone spots you. Hope you didn't dump Cha!
 

Until dice are rolled for initiative stealth works differently than the cover and concealment model people keep talking about. It's not a round per round movement necessarily though. You are hidden in a shadow and wait until the guard is distracted by a noise, attractive person, lord what's his name and move past him while he isn't looking.
Quoted for truth.

I rarely call for a series of stealth rolls. There's just one whenever there's an opportunity for the sneak to get caught. If you're trying to sneak across towards a castle with a guard on the wall, I'm going to ask some questions.

If it's high-noon on a clear day across what's essentially an empty parking lot, the answer is "you can't hide". If it's a wheat field in September, you've got a pretty good shot. If you're a Ranger, you might even be able to sneak across a freshly mowed lawn. If there's a forest or orchard that goes pretty close to the wall, then you're probably getting advantage -- or even a freebie. If it's night, then even dim light provides light obscurement, which is sufficient for a base hide check. Fog, smoke, etc. would have a similar effect. That should answer the basic questions.

The biggest complication is probably how to handle broken cover (i.e. when you have non-adjacent areas of cover) without any obscurement. Any idiot can remain hidden while stationary behind a wall; it's dealing with movement and open spaces that actually requires a skill roll. It's possible to zip between, say, stacks of crates in a warehouse while sneaking. I generally play this cinematic, with some nods to having run with some sneaky bastards in high school.

So, how do I handle that complication? At the simplest, can the sneak make it from safe spot to safe spot in half his move or less? If so, make the skill check because that's what tells you whether you were able to do it while the guard's back was briefly turned, or something similar. Note that Rogues can get the extra Dash action, which gives them full movement to make it. Pretty cool.

What about peeking around a corner (or over the lip of a roof)? As I said, it doesn't actually take any skill to hide behind full cover. Next time you're inside your house/apartment/dorm room, look towards your neighbor's abode, without stepping out. Can you see him? That has nothing to do with him trying to hide. There's at least one freaking wall in the way. The Stealth skill comes into play when you want to be able to continue to interact with someone, even if that interaction is actively continuing to avoid whatever it is.

So, unless there's some circumstance that you haven't mentioned, the roof seems like a textbook (rule book?) case of a standard Stealth check. The only thing I can think of that might change that is if they'd seen you before you tried to hide and you explicitly wanted to maintain line-of-sight the whole time (i.e. your head was always sticking out).

One other thing I'll mention is how I handle attacking from hiding: I let characters step 5' from cover to attack and retain the benefits of hiding. Why? because it's the easiest way to do math. With a missile weapon, it's effectively a moot point unless I want to start trying to make the sneak take cover penalties, which starts down a path of making it so Rogues can't sneak attack from hiding. For melee attacks, it allows a lunging ambush in a very limited set of circumstances (because you can only ready an action, the sneak has to do it on their turn).

Also, I do allow the Rogue to duck back behind the cover and spend his Cunning Action to hide and sneak attack again next round. Why? because it totally fits with most action movies where the hero is trapped behind some sort of cover and pops up erratically to shoot the bad guys. Plus, I've used that tactic in paintball to very great effect, so I know it's realistic to be able to catch someone by surprise; even if they know you're there, they don't know exactly when you're going to engage.
 

(Expendable) minions (ideally fanatical and/or fabricated, but cold hard gold-bought and/or good 'ole coercion works in a pinch) and misdirection.

They can have as many alarms as they need - there's a finite number of guards (I would hope!) and when alarms start triggering all over the place there's only so many places the guards can be at one time.

Send the minions in to trigger the alarms, you waltz in during the chaos and nab the nabbables. Disguise yourself as a guard, servant or visiting dignitary just in case someone spots you. Hope you didn't dump Cha!
Yup. With that many alarms, false positives are apt to render the whole system worthless.

It's like car alarms. When you hear a car go into a frenzy of honking like a yappy little dog, what do you do? Run to catch the thief? Call the cops? Of course not, because it's almost certainly a false alarm. You swear at the car owner and go about your business, trying to ignore the din.
 

Here's the language:
You can't hide from a creature who can see you clearly.

That can (and is) interpreted to mean either "is theoretically capable of seeing you clearly, regardless of what else he's doing" or "actually is seeing you clearly." Both are valid interpretations.

For DMs who like stealth, or at least are willing to let players who like stealth actually enjoy being stealthy, the latter interpretation means that you can assume that guards sometimes turn around, or doze off, or talk to each other, and that a good ninja knows how to time movement (or use distractions) so that they are never directly observed.

So let's say you're in a brightly lit hall with a few columns, and at the far end is a doorway with a guard. Can you stealth past? If the DM wants to let you try, the narration would be that the stealther starts off fully Hidden, then slips from column to column when the guard isn't paying attention, and then finally...perhaps rolling with disadvantage...throws a pebble behind the guard to make him turn around and then sneaks up right behind him. As the now suspicious guard whirls back around to peer at the hall, the stealther moves with him, always staying out of his peripheral vision, and then quietly slips through the doorway.

Again, a DM doesn't have to allow this to occur, but if you want to allow "cinematic" stealth you can, without breaking RAW.

The problem I have with the much stricter interpretation of "can see you" could be taken so far as to mean that the stealther can't even peer from around the first column to see what the guard is doing, because at that point the guard "can" see him clearly. That doesn't sound like any fun to me.
 
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But yeah, the GM wants us not to murder everything so I'll have to try to talk about it.
"I want you to not murder everything "

"I'm trying to sneak past everything so I don't murder it. But I live in a world where everyone is a beholder, so I'm left with no choice but to murder everything."
 

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