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So for reference page 19 of the PHB talks about hiding and says "The Dungeon Master decides when circumstances are appropriate for hiding" so cover/obscurement/etc... all comes after the DM deciding if you can hide or not. This doesn't stop the characters from doing things like hiding behind a...

You aren't hiding unless the DM says you can take the hide action, and they can if they want, decide you can only take that action right before it's going to actually come up. So as an example, the PCs are travelling somewhere and decide to move at a slow pace and travel stealthily. The DM is...

As a PC, Frost Goliath + Crusher + Slow weapon mastery can mess a creature up pretty bad. Valour Bard with Ray of Frost and a Sling even more so.

As a note the DM is by RAW supposed to be in charge of when a PC can attempt to hide, so there's an argument that says you can't attempt to hide at will until you you hit that DC 15. Instead players who chose to stealth when there are no potential hostile creatures nearby simply don't roll until...

Yes in combat stepping out and attacking I feel should be at advantage, whether you get advantage because they didn't see you approach them or because your sudden unexpected appearance has caught them flat footed and vulnerable is basically irrelevant, you get advantage on the first attack and...

It's in the Rhythms of Play part of the PHB which is essentially players tell the DM what they want to do and the DM narrates what happens, typically using dice rolls when the outcome is uncertain. Step out into full view of the guards where there's no chance of maintaining stealth, the DM...

It's worth keeping in mind even though both approaches are very different, neither is right nor wrong. So long as going into the game everybody is on the same page about how it's going to work then it's a good thing that the rules can support those two different visions. If running a horror...

This is where I think the DMG in particular kind of fails, I fully support the DM having to determine in the moment stuff like facing and whether you can stealth over clearly defined rules that are very likely to end up problematic. But that's exactly why there should be a section/paragraph that...

Obviously what's good/fun for someone isn't the same for someone else and there's no right/wrong because it's all subjective. But having said that I just can't buy the argument that equates DM discretion with house rules, DMs are asked to make judgement calls by RAW. Stealth by in large falls...

I could be wrong here, but your responses come across as claiming that the DM making a ruling on facing is not RAW/RAI, which sure is their prerogative, but a strictly RAW reading is actually 360 degree vision. If that's the case I think you're wrong, the RAI & RAW is that it's DM discretion...

This isn't true, there's lots of things that exist but don't have explicit rules defined which simply means the DM decides. Not sure if in the new PHB they have the same line, but in the '14 PHB says in combat creatures stay alert for danger all around. Essentially in combat they are constantly...

Yes which is why in someways having vaguely defined rules that are up to the DM to interpret has it's benefits. It's why the DMG advice on the subject should be about how the different interpretations/rulings impact the game so that DMs can rule in a way that produces the tone of game they want.

To me this would be an issue, too many rolls and failure becomes inevitable, I'm already at 4 skills checks including picking the lock, and no doubt have a bunch more skill checks ahead of me inside the keep. So unless you are treating these failures as something other then being seen then...

Playing along, my plan would be climb the walls and sneak into the keep from the top. Climb speed and BA Dash means I could get from the closest area of cover to the top of the wall while still having my action which is probably a Dash to get off the roof and into the keep, or failing that to...

Do you also have to roll a check every time a character goes up or down stairs because there's the possibility of tripping? Or do you just say it's too unlikely to bother with a check.

Trying to be quiet while not moving isn't something that you should reasonably fail at doing. If there's something specific that would make you say sneeze or cough like say a bunch of pepper in the air then a Con saving throw is probably more appropriate then a stealth check.

Personally I think the idea that leaving it up to the DM to adjudicate whether it's possible or not is the right approach. There's just to many edge/corner cases for the rules to handle well. The big failing is that the DMG should have spent a few pages going over if not how to make those...

Survival makes the most sense, but honestly I'd suggest just asking the players to justify whatever skill they want to use. For example, both Survival and Nature can be used to find a spot where fishing checks will be done at advantage or have a lower DC. Let the players decide the approach and...

But then how do you define LoS? There will be situations where you have LoS to someone but still not see them because they've camouflaged themselves well, or because only a small portion is visible, etc...

Maybe tailing someone was a bad example because there's two components, you seeing where they are so that you can follow them and not lose them, and remaining unnoticed yourself. I was talking more the second part. But the broader point is that not all stealth tasks are the same difficulty...