D&D 5E Can someone clarify the mechanics of surprise for me?

Yes, you can actually attack hidden targets, but you need to guess its position or else it's auto-miss. Even if you guess the position correctly, it's still disadvantage on the attack roll.
 

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In terms of order and initiative.

A good example is one situation I had where a character with the Alert feat got to act before someone else who initiated the combat. The PC's were talking to an enemy and one of their NPC allies had a high enough stealth while invisible that none of them knew he was there. He attacked the enemy from hiding, starting combat and therefore initiative, but the PC with Alert acted first and attacked the enemy before the NPC could even complete their attack that started​ the combat.

That's some seriously time-warping reflexes right there.
Part of the problem you have is that you are assuming the Attack is what starts the combat. I start initiative with the intent and ability to harm. I don't roll initiative at 1000 feet, for example, because that's pointless (no one has the range to hurt each other). I don't allow someone to get a free attack just because they say "I cut him down," either.

In your example, assuming the Alert Character didn't have enough Perception to notice the assassin, the combat begins when the Assassin intends to attack. Initiative is rolled, and the Alert Character is before the Assassin. The Character doesn't know there is an assassin, only that something is wrong. Perhaps the assassin shifted himself to make a noise, but not enough to reveal his location. Perhaps the NPC they're talking to hesitated at the wrong time (anticipating the attack). Perhaps the Alert Character just has a hunch. They KNOW something is wrong, but not what. Attacking an enemy isn't a bad idea in such a case, especially if you suspect treachery. The same thing could happen without the assassin too, if you had a paranoid player/PC (they just don't have the excuse to the other players).
 

According to RAW, passive perception applies even to creatures that are not actively looking for threats. Some sections in the starter set also indicate that this is true.
Its a subtle, but important to understand what "passive perception" actually means, difference; passive perception applies because creatures are assumed to be constantly looking for things while their eyes are open.

Like how right now I can see my computer monitor, but I'm also able to notice every time my wife's screen saver changes which dragon image is displayed even though I am not specifically looking for changes. I would also notice if someone walked through the door to our office despite that I am not actively watching the door because my peripheral vision happens to fall upon the door area.

And because the word "passive" in "passive perception" (or any other passive check) is referring to the player and die rolling; not to the character and whether or not they are using their senses. A check without rolling, not an action without acting.
 

Of course, PCs being surprised by monsters (and vice versa) is an entirely different thing from players being surprised by DMs (and vice versa). There are no rules about the latter. That's what makes it fun.
 

In terms of order and initiative.

A good example is one situation I had where a character with the Alert feat got to act before someone else who initiated the combat. The PC's were talking to an enemy and one of their NPC allies had a high enough stealth while invisible that none of them knew he was there. He attacked the enemy from hiding, starting combat and therefore initiative, but the PC with Alert acted first and attacked the enemy before the NPC could even complete their attack that started​ the combat.

That's some seriously time-warping reflexes right there.

The thing is, everything is happening at roughly the same time. In order to resolve conflicts we use turns, rounds, and initiative.

Each round is about 6 seconds long.

In your example the Alert character acts a split second before the would be assassin does their thing.

It is the job of the DM to narrate the events so they make sense.

Or put it another way, if you think of it in terms of each character going in sequence then it is wonky from the start. You could have 200 characters all in one combat, and each waiting until the next does their thing, all within 6 seconds.

Instead it is better to just accept it as the best way we have of resolving the conflict. There are alternatives too. It isn't surprise that makes it wonky, it is taking initiative order as a literal line where characters are waiting their turn.

One alternative would be to have everyone declare their actions at the start of each round. Then the DM narrates the results of the actions as they see fit.
 

I'm not a fan of the ruling that the person who goes first in initiative is aware of anything.

They don't know an attack is coming.

They don't know there's something hidden there.

They don't even get a "bad feeling."

All of that disempowers the Stealth-er, making failing to win initiative tantamount to also failing a Stealth check. And one thing Stealth should be good for is sneaking up on someone without them being aware of it.

My most recent take on surprise is that it works like a readied action - you move into position, make a Stealth check, and then, assuming nothing has caused you to move or anything, you ready an action to attack.

When the trigger happens, you can attack. After the trigger, initiative is rolled.

This seems to make the most fictional and mechanical sense to me, and avoids mechanical and narrative weirdness like "the NPC stops being surprised for no reason," and "you already declared your action, so you don't decide what you do on your turn."
 

This seems to make the most fictional and mechanical sense to me, and avoids mechanical and narrative weirdness like "the NPC stops being surprised for no reason," and "you already declared your action, so you don't decide what you do on your turn."

We're talking about the Alert feat though.

Usually when someone is hidden and has surprised their opponents those opponents don't get to do anything on their turn because they are surprised. If they have a special ability they may be able to react to what the hidden opponent does after they do it, but that's it.

Alert means that you can't be surprised. I'm not a big fan of it, but if you allow it in the game, then you should honour what it does.
 

We're talking about the Alert feat though.

Usually when someone is hidden and has surprised their opponents those opponents don't get to do anything on their turn because they are surprised. If they have a special ability they may be able to react to what the hidden opponent does after they do it, but that's it.

Alert means that you can't be surprised. I'm not a big fan of it, but if you allow it in the game, then you should honour what it does.

And what it does is mean that after that readied-action attack goes off, you can act normally when your turn comes up in initiative.

You aren't surprised - you take your turn normally. This doesn't mean you can't be ambushed by a creature you're not aware of.
 

I'm not a fan of the ruling that the person who goes first in initiative is aware of anything.

They don't know an attack is coming.

They don't know there's something hidden there.

They don't even get a "bad feeling."

All of that disempowers the Stealth-er, making failing to win initiative tantamount to also failing a Stealth check. And one thing Stealth should be good for is sneaking up on someone without them being aware of it.

My most recent take on surprise is that it works like a readied action - you move into position, make a Stealth check, and then, assuming nothing has caused you to move or anything, you ready an action to attack.

When the trigger happens, you can attack. After the trigger, initiative is rolled.

This seems to make the most fictional and mechanical sense to me, and avoids mechanical and narrative weirdness like "the NPC stops being surprised for no reason," and "you already declared your action, so you don't decide what you do on your turn."

I agree with you conceptualization, but not your approach, as it can lead to being able to get of 3 attacks before the target has a chance to act. I rather prefer, in those cases, just to set the initiative of the ambusher to go first, and roll from there. This is just an automatic win of the ability check, and, since you as the DM have determined there's no uncertainty in who goes first, is still within the spirit of the rules.

However, as I've come to this conclusion while running a game, I haven't made any changes in my current game and still roll initiative and try to muddle through the weird corner cases as best as I can.
 

And what it does is mean that after that readied-action attack goes off, you can act normally when your turn comes up in initiative.

You aren't surprised - you take your turn normally. This doesn't mean you can't be ambushed by a creature you're not aware of.

Sorry, I'm not following.
 

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