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Message: <blockquote data-quote="DEFCON 1" data-source="post: 6882948" data-attributes="member: 7006">In this case... trying to hide on a roof on a bright day would depend entirely on what the DM would rule as far as line of sight issues.  First off, "total concealment" doesn't really exist as a concept in 5E-- there are no rules for "concealment" per se.  There is Cover... but that only applies towards targeting and bonus defense.  For Hiding though, it comes down again to being Obscured-- usually Heavily Obscured.  Ordinarily, you would need to be behind something to create that Heavy Obscurement and thus try to be Hidden.  If you were over the peak of the roof, that would probably apply; behind a chimney; depending on the height of the roof and the angle down to the road below, just being a distance back from the roof's edge might break line of sight.  In those cases, I personally would allow you to roll a DEX (Stealth) check to try and become Hidden.But in these cases... it would come down to DM adjudication as to whether the rogue would themselves be allowed to look out around the Heavily Obscuring terrain to try and see the targets coming.  Some DMs (like it seems, yours) might rule that just sticking your head out once while the target was in the area would immediately break line of sight (and thus removing the Hidden status)... but I myself would possibly rule that if you were to stick your head out to look at the target, I'd just give the target Advantage on their Passive Perception check to notice you (which is a +5 to Passive Perception) since you are making a part of yourself seen for only a quick moment.  But to eliminate that possibility altogether... I (as DM) would allow the PC to do the old "mirror on a stick around the corner" trick to watch the target without taking themselves out from behind the Heavily Obscuring terrain, and thus maintaining his Hidden status without any issue (and the target thus does not gain Advantage on their Passive Perception).  But another DM might not allow that.It really comes down to talking with the DM out of game and coming to a consensus on what the DM is ruling as far as being out of line of sight is concerned, and what you need to have to try and gain the Hidden status with a DEX (Stealth) check.</blockquote>

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