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Just before confrontations with the "boss" of a dungeon or adventure, I often like to ham it up a bit and let the BBEG-of-the-week gloat a bit about how brilliant their plan is, or what a thorn in the side the PCs have been, or about how the PCs will never win, etc. Usually this is pretty brief, but it sets the tone of the encounter, and generally allows the players a window to say anything they wanted to say before we start the final combat. It also gives the players a chance to ask questions in case they missed something about the plot and they'd like it cleared up in-game.

Usually this goes just fine, and the players seem to generally like it, but sometimes a player who doesn't quite fit the narrative-focused mindset of the rest of the party gets a little restless and throws the first punch. Again, usually this doesn't happen, but occasionally it does.

If a player decides to do this in a given speech, how should I respond? I've defaulted to making everyone roll initiative when a player says they attack in a situation like this. After all, I don't really want to reward the players for attacking in the middle of dialogue, since I (and most of the players) find the dialogue to be really fun, and it mostly exists for the players' benefit, anyway. Besides, when the villain finally attacks, they don't get a surprise round -- their attack just means everyone has to roll initiative.

On the other hand, I feel like the player who threw the first punch might feel a little cheated in not getting a free shot off. They might be trying to have a cool moment of emulating Han Solo, blasting the enemy when they're caught off-guard gloating. Since I make them roll initiative, though, I rob them of this moment and Greedo might get the first shot off, anyway.

So, in this situation, should the player who fires first get a surprise round, or am I handling it correctly in making everyone roll initiative?

5e is the relevant edition, here. Quoting the rules is nice, but I'll take a well-reasoned argument for one way of playing or the other over a strictly RAW answer.

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D&D5 - The bad guy should not be surprised.

PHB, p.189 - Surprise

A band of adventurers sneaks up on a bandit camp, springing from the trees to attack them. A gelatinous cube glides down a dungeon passage, unnoticed by the adventurers until the cube engulfs one of them. In these situations, one side of the battle gains surprise over the other.

The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

As @KorvinStarmast stated, there is no such thing as a surprise round in 5E. A surprised character is simply not able to move, take an action or a reaction on his first turn of the combat.

In your situation, the bad guy is clearly facing the characters when doing his speech, so unless he is fanatically speaking to his hidden god of evil somewhere in the skies, he will see the character doing his move and won't be surprised.

If the party was speaking with a friendly noble NPC, for example, and a PC decided to attack suddenly, the NPC should be surprised, because he wasn't aware of the threat. When a BBEG faces a party of characters, it seems obvious that they are antagonists/foes/enemies and that each side is a threat to the other. In the end, it is the definition of threat that makes a difference.

Also, giving the player a round during which he alone can act might lead others to abuse this mechanic.

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    \$\begingroup\$ To add onto this answer, it might be a good compromise to allow the player to only roll their attack (not any movement) prior to initiative, and everything else follows initiative order. This might help curtail abuse, while also keep the player from feeling cheated. \$\endgroup\$ – Liesmith Mar 9 '16 at 12:59
  • \$\begingroup\$ @Liesmith I.e. use 3e-style surprise rounds? ;) \$\endgroup\$ – fectin Mar 9 '16 at 14:02
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    \$\begingroup\$ Another possible solution is to give the attacking player a small bonus to their initiative. The BBEG obviously expects to fight the players, so no surprise round. But you could probably argue that cutting him off mid speech with an attack gives you a small advantage in reaction time \$\endgroup\$ – D.Spetz Mar 9 '16 at 21:30
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    \$\begingroup\$ I'd advise against offering a bonus to initiative. Think about what you want to achieve with the ruling: given "sometimes a player who doesn't quite fit the narrative-focused mindset of the rest of the party gets a little restless", it sounds like the player is acting against something the rest of the table is enjoying, so you wouldn't want to encourage that. \$\endgroup\$ – Quentin Mar 10 '16 at 2:17
  • \$\begingroup\$ One thing - "Any character or monster that doesn’t notice a threat is surprised" - "noticing a threat" isn't necessarily the same as "can see the creature". If the party tried to hide that they're about to attack, I'd allow them to roll Sleight of Hand against the villain's Perception to see if they can ready their weapons surreptitiously, without the villain spotting it. Use the villain's active Perception if he's watching them for signs of trouble, passive if not, allow adv/disadv if there's relevant circumstance (the room is dark, the villian is gesturing grandly out the window, etc). \$\endgroup\$ – anaximander Mar 10 '16 at 11:08
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The bad guy may or may not be surprised

The relevant rule is:

The DM determines who might be surprised. Any character or monster that doesn’t notice a threat is surprised ...

If you decide the circumstances are such that the villain (and maybe the other PCs) might be surprised - that they do not regard the PC as a "threat" - you make the appropriate check. In the circumstances, a Dexterity (Stealth) vs Wisdom (Perception) is not appropriate but Charisma (Deception) vs Wisdom (Perception) is.

Personally, I think the villain would regard the PC as a "threat" and wouldn't be surprised, however, it is easy to imagine circumstances where interlocutors would not be anticipating spontaneous violence - surprise would then be appropriate.

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Since there is no [rules-as-written] tag, I will give a non-rules based answer: your group has to decide this. Even if the rules (would) allow it, but your group wants to make the "here is my plan..." chat fully to the end, robbing the group of that talk is not good. If they are OK with that, let the situation go.

What goes to the rules, Dale M has said it right: the GM decides if the villain is surprised.

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PHB Pg. 189:

The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

In the mentioned case with the villain:

  • Neither side is trying to be stealthy.
  • He is a villain making a speech. He sees the character, and since he is a villain, he does regard him as a threat.

The villain is not surprised.

However, if it was an ordinary villager speaking for an ordinary reason:

  • Nobody would be trying to be stealthy.
  • However, the speaker probably would not notice the threat, even if he does see the character himself. In this case, it is up to the DM.
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