At the beginning of an encounter, what happens if both sides are being stealthy?
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The same thing that would otherwise. Both sides roll to remain unseen / notice the other group (using your flavor of passive checks / hidden rolls / whatever). Unless one of the sides actually wants confrontation, they can even pass each other like ships in the night.
Side note: you might consider giving Disadvantage to hide from someone you cannot see.
Szega
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I understand your reasoning on the side note but that would set precedent that any rogue/ranger or other scout stealthing forward outside of combat as they oft do, would have disadvantage in a dungeon or something. Therefore I would discourage that myself. And in the example both sides would have disadvantage in this case because neither side saw the other. – Slagmoth Jun 19 '17 at 17:45
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1More to the point, how do you have a stealthing player roll disadvantage on his stealth roll for a character he cannot see without telling him there is a character he cannot see? – Doremar Jun 19 '17 at 18:42
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@Slagmoth They wont always have DA. If the opposition is not stealthy, the rogue would see them as soon as it becomes relevant. And yes, both sides have DA to stealth there, why would that be a problem? – Szega Jun 20 '17 at 00:21
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@Doremar "You can't see anyone in the corridors, roll it with Disadvantage." It still might be empty. He didn't get any new information he wouldn't have otherwise. Either someone is hiding well, or there is noone there. – Szega Jun 20 '17 at 00:24
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1@Szega The logic is flawed. The idea of using stealth is to keep from being detected, that would include moving quietly as well as choosing paths that would include cover and concealment, these are things that someone proficient in stealth would know. Imposing disadvantage on all rolls versus those you don't see/hear means that you hamstring scouts entirely. The rules allow for those that are observing you to totally negate your efforts anyway so this smells like a double whammy. – Slagmoth Jun 20 '17 at 01:01
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@Slagmoth How would someone observing you null your stealth? And cover is relative to the observer. How do you find cover from someone if you do not know which areas they can see? It is not about just sight. If you can hear someone that is good enough. But the original question is about another party that is sneaking. It is a corner case I do not expect to see often. – Szega Jun 20 '17 at 01:06
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@Szega PHB p177 the Hiding Sidebar. "You can’t hide from a creature that can see you, and if you make noise (such as shouting a warning or knocking over a vase), you give away your position." – Slagmoth Jun 20 '17 at 12:38
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@Slagmoth Not being able to hide in plain sight is to be expected. "Not knowing where the enemy is" and "the enemy seeing you" are not the only possible states. – Szega Jun 20 '17 at 13:06
1.Determine surprise. The DM determines whether anyone involved in the combat encounter is surprised. Seems like you are confusing start of hostilities with start of an encounter. – Wyrmwood Jun 19 '17 at 22:03