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Message: <blockquote data-quote="Lyxen" data-source="post: 8604638" data-attributes="member: 7032025">The thing is that once more (and as usual more the source of disagreement than the ruleset itself) it is hugely circumstances dependent. There is a whole gradation of possibilities from "having a casual dinner with a relaxed king who is basically trusting the people at the table" and "An extremely tense dinner where the possibility of treachery is all but certain and everyone is watching everyone, on full alert".As there are differences between doing something that might be expected like drawing a weapon, jumping at the king's throat or casting a spell, and doing something totally unexpected (but for me the table flip would not qualify, and would also be circumstance dependent for example if it's a massive table, it would be unlikely to succeed but all the more surprising if it was, etc.).And my point of view is that 5e sort of caters for all of these. Surprise occurs when some people are not aware of other aggressors. The standard rule is that it usually is because the aggressors have not been detected. In the case above, and if the situation is tense, it's obvious that the (potential) aggressors are in plain sight, so there would be no surprise. But if the situation is very relaxed, someone doing something out of the blue might qualify as an "unnoticed aggressor" as all other people (not in on the secret aggression) are not aware of the possibility of violence.In all cases, it's not the act itself that starts the initiative, being an act that stats a combat it means that it's only the declaration by the player that he wants his character to commit the act, the act will be one of the actions of combat, and that is the 5e rule, plainly.However, in the second case, the DM might rule that because the atmosphere was relaxed, aggression was not expected and the declared act is "out of the blue", surprise happens, and that act is indeed the only one happening in the first round as everyone is surprised that there is an aggressor present.I think this would cater for your case fairly nicely.The thing is that it should not be abused, once more, by players who think themselves clever there. The NPCs are as clever as they are, they can be as or even more aware (adventurers have a reputation for violence, and some of them might have it in particular), and they can be watching for especially that kind of behaviour. So the player cannot expect automatic surprise just because he thinks it's clever to attack in the middle of a discussion. It's not, in a dangerous world, people will expect that and will not be surprised.And in any case, turnabout is fair play, if he pulls this, the next assassin will surprise him for exactly the same reasons... I would not do this in the game, not only is it not my preferred method of play, but it's not the principle of 5e as written, but it might be used to point out exactly that to the player, fairness cuts both ways.As a side note, this is for me one of the great benefits of 5e and its principles of Passive Perception being always on and protecting characters (including NPCs) against that kind of surprise, because in a dangerous world, characters are aware of their surroundings and watching for danger. It avoids players thinking that they are clever and declaring all the time "I watch my surroundings, I'm looking for threats" and whining when they are surprised "but I was watching for threats". It wastes time and energy for basically nothing, and it leaves everyone open to stupid "gotcha" which annoys everyone. The default is that the passives (in particular perception) are on, there is no need for these declarations.Now, if someone is particularly distracted or is obviously not very aware (like an old king in his drink), it's OK to give disadvantage to PP or even give an automatic failure, but it should not be the rule and it should be fairly visible and justified. After all, the king might be Conan... <img src="https://cdn.jsdelivr.net/joypixels/assets/8.0/png/unicode/64/1f61b.png" class="smilie smilie--emoji" loading="lazy" width="64" height="64" alt=":p" title="Stick out tongue    :p"  data-smilie="7"data-shortname=":p" /></blockquote>

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