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You can use an unassuming character as bait as long as they're not an opponent. That assassin's can't get surprise in a disguise is RAW, and not absurd at all. Watch the video linked previously if you want to understand how the 5e designers viewed surprise. Giving a disguised Assassin the...

The Sage Advice compendium makes it clear that "you aren't surprised if even one of your foes fails to catch you unawares", and what that means is that noticing a threat and one of your foes not catching you unaware mean the same thing, at least for surprise purposes. The video with Jeremy...

If anyone who is uncertain about how the designers of the game felt that combat should start want to hear from a designer, check out this Sage Advice video by Jeremy Crawford, the lead designer of 5e. He makes it clear that in the "surprise" dagger attack situation, that's an initiative roll...

This is an argument from first principles and not an argument from the text of the rules. Basically, you're just saying : "this is what I like." Ok, great, you do you. But from the rules as written, it is a requirement for all members of one side of an ambush (the only case where the surprise...

I would be very surprised, since my Mom is dead, buried 6ft. under, and would definitely be in hiding. I don't have the same conception of the game as you do, or the purpose of the rules. The rules are there to provide fairness to the players, and to keep the balance of power between the...

If you've got an argument from the text, I'm all ears. Otherwise, you do you.

Also if you take a look at this question from the Sage Advice compendium, I think that lends some guidance as well: What this says to me is this: when you're determining surprise for an ambush you would use Stealth checks (Hiding), and if you're determining what happens in an ambush after the...

I simply disagree with your interpretation of RAW - the surprise rules do in fact say that surprise requires hiding. The rules on p. 189 say that the DM determines who might be surprised, not that they decide who might be surprised. And it follows that up with the procedure that the DM is to...

Maybe we do have a disagreement. I think the right interpretation of the rules as written is that "noticing a threat" is absolutely meant to be read exactly the same as "noticing an opponent", regardless of what the creature doing the noticing believes about that opponent. We addressed our...

The 5e concept of surprise springs from the idea of an ambush : something that the party decides to do together in unison. For example, PHB p. 189 : "A band of adventures sneaks up on a bandit camp, springing from the trees to attack them." I'm well aware that surprise is something experienced...

You're written a lot to respond to, so I'll take it in chunks. I'm uncertain that we have any real disagreement on this first point. Your allies clearly notice you, and that is clearly not enough for surprise where opponents must notice a threat. So, I stand with my previous statement ...

I don't disagree - my group has played together for 7 years under just that sort of an understanding. But my players a bit more interested in making advantage of edge-cases, and after having experienced a lot of them over our years of play together, we've decided to batten down our...

I think your comment is trailing some of my subsequent replies, where I and my group have come back around to the idea that "Being Stealthy" and "Hiding" are the same thing. Check out my intervening comments if interested, and again I think you for your insights.

And taking into account the same considerations, an update to the definition: Definition of "Being Stealthy" : Being stealthy represents an attempt to hide when your opponents are either distracted or cannot perceive you clearly, decided by the DM using the same criteria as for deciding...

Thank you @Flamestrike for your insights! Here's where my group is at now on our FAQ: Are being Hidden and being Stealthy in combat the same thing? Yes, even during the movement to your hiding place. Hiding as you retreat from a creature is as difficult as remaining hidden as you approach...

It's true that you can't take the "Hide" action, but that doesn't mean you can't be Stealthy. Even if you're in plain sight, maybe you can "slip away without being noticed" as per the Stealth definition. Circumstances must be such that the character can do that, but in the heat of combat...

I'm sorry, that's just not Rules as Written. You drop them in if you're following RAW. Re-read the side-box "Combat Step by Step" on p.189 of the PHB, particularly Step 2: COMBAT STEP-BY-STEP 1. Determine surprise. The DM determines whether anyone involved in the combat encounter is...

I'm not telling you what your interpretation of the rules should be, I'm simply looking to bring in other opinions to consider to influence ours. Nothing says you have to play D&D by the Rules as Written, even the Rules as Written. You do you. The justification for why the world works as...

As to why player's decide pre-combat if they will be hiding, that's because players should have autonomy over their character's actions. I suppose you could have a house-rule that if an encounter is laid out as an ambush, that this means the players automatically hide, but I think my players...

An assassin masquerading as a member of an orchestra can't surprise because they aren't hidden. If you take a look as the Assassin archetype for a Rogue (PHB p. 97), their Assassinate (and later Death Strike) ability is not predicated on getting surprise (known for certain because they get an...