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Message: <blockquote data-quote="Mercule" data-source="post: 6883015" data-attributes="member: 5100">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.</blockquote>

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