|Dragon Magazine #88 cover by Jim Holloway|
Based on recent social media chatter, it appears GM’s have some confusion when adjudicating stealth and hiding, and players believe their Rogue skills give them Advantage more than the rules as written would suggest. A re-review of the rules as written with a few examples should help.
To break this down a bit, let’s start with the rules as stated in the SRD 5.0 (bold emphasis added).
Make a Dexterity (Stealth) check when you attempt to conceal yourself from enemies, slink past guards, slip away without being noticed, or sneak up on someone without being seen or heard.
The GM decides when circumstances are appropriate for hiding. When you try to hide, make a Dexterity (Stealth) check. Until you are discovered or you stop hiding, that check’s total is contested by the Wisdom (Perception) check of any creature that actively searches for signs of your presence.
You can’t hide from a creature that can see you clearly, and you give away your position if you make noise, such as shouting a warning or knocking over a vase. An invisible creature can always try to hide. Signs of its passage might still be noticed, and it does have to stay quiet.
In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you. However, under certain circumstances, the GM might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack roll before you are seen.
When you hide, there’s a chance someone will notice you even if they aren’t searching. To determine whether such a creature notices you, the GM compares your Dexterity (Stealth) check with that creature’s passive Wisdom (Perception) score.
So there are a few things that are implied by the above rules that could be stated more clearly, or at least clarified with examples.