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Message: <blockquote data-quote="Oofta" data-source="post: 6882967" data-attributes="member: 6801845">As others have stated, stealth is really, really up to the DM.  The way I generally handle stealth may be different from any other DM.I can tell you how I would roll and why.  In general I start with the rules and then try to apply common sense and what would make sense to me.First, setting up an anti-magic zone without broadcasting it somehow is not something I would normally do.  However, there are several reasons why someone might lose the spell.Outside of combat I do not assume that guards are looking all directions at all times.  But if you are in a a hallway and the guards are looking down that hall, they will see you.  If it's night, it depends on how well they can see in the dark.If the guards are looking down a hall in only one direction and you've successfully snuck past them, yes I would allow a check since they are only actively looking in one direction.  That, and guard duty is incredibly boring ...There are various times I'll enforce a reasonable "facing" rule, but possibly impose disadvantage on the stealth check.  If you want to sneak across a wall and there's a guard walking patrol for example I'll let you time your crossing so you can sneak across when he's not watching.  If, however, you didn't pay enough attention and realize there's a guard in a tower watching the same section of wall you will still be spotted.How paranoid are the people you are tying to ambush?  If they're unsuspecting I might allow this (in bright daylight it might be with disadvantage).  However I might also allow for some creativity here - set up  a distraction to draw their attention or be prone on the roof while using a small mirror to look down onto the street.If this is someone who is suspicious and has a reason to be scanning the rooftops?  Probably not going to work.  It's going to be very situational though.  A wide street, long lines of sight, a quiet street with little to distract the people being ambushed are all going to come into play.Ultimately though you have to have this discussion with the DM and try to figure out what makes sense.  He's the arbiter of the rules and stealth is not a guarantee no matter how high your roll is.</blockquote>

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