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Message: <blockquote data-quote="Li Shenron" data-source="post: 6882848" data-attributes="member: 1465">There's a hundred ways to adjudicate stealth in 5e... <img src="https://cdn.jsdelivr.net/joypixels/assets/8.0/png/unicode/64/1f642.png" class="smilie smilie--emoji" loading="lazy" width="64" height="64" alt=":)" title="Smile    :)"  data-smilie="1"data-shortname=":)" />My personal opinion is that each scenario is different, and thus consistent ruling (which normally is widely regarded as a good thing in gaming) might actually get in the way.So for instance in case of your roof example, I would not be able to answer in general. It depends on the roof's location and shape, the sources of light, the time of day, where are your opponents and what are they doing, how are you dressed, even what is the weather like, etc. As a DM, I'll describe some of these stuff, let the player ask about more details, and state her plan. I would definitely tell the player beforehand what kind of rolls she need to make in order for her plan to work, so she can re-consider it if the odds are too low.So that's my only suggestion to you: ask your DM to talk to you about the situation before you roll those dice. After all, if your PC is the expert at stealth, she should be able to assess the situation before doing anything, and back off if chances of success are too low. Just like when someone is attempting a jump, the DM tells her how far she has to jump, so why can't the DM do the same for stealth?And I agree that in-combat and out-of-combat stealth works differently. In-combat the situation is generally more standardized and follows the rules more carefully. In case of sneaking in combat, in general I don't make it easy, on the assumption that everyone is moving around all the time, and so to me it makes sense that they have 360 degrees visibility (at least because I don't use facing) even tho they are busy fighting. But out-of-combat there are plenty of situations when the guards are facing one way and not the other (and they aren't constantly spinning around for the whole 6-hours shift!), and creeping up behind someone is a totally valid idea that shouldn't be vetoed by rules mostly meant for combat.</blockquote>

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