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Message: <blockquote data-quote="pedr" data-source="post: 4970284" data-attributes="member: 33464">You roll intiative when both sides are aware of the other and at least one side is planning to take hostile action (i.e. there will be 'combat'). If one side is aware and the other is not, and the aware side plans to take a hostile action, the aware side rolls initiative, takes their surprise-round actions in initiative order, and then the unaware side rolls initiative and the first full round starts. You don't roll intiative (though you may track rounds) if only one side is aware of the other but is not taking hostile actions. Of course if the non-hostile actions they take make the other side aware, you may need to roll initiative - but I'd delay that until there was the possibilty of actual hostile action between the sides.The PH states that you cannot ready an action outside combat. The DMG goes through the initiative trigger conditions, if I recall correctly. There is a problem with 'surprise' and sudden switches from non-hostile discussion to hostile action - the RAW does not seem to permit that, as because both sides are aware of each other when combat begins there is no surprise round. Initiative perhaps measures how quickly you can react when someone you can see begins to take a hostile action, so they go to loose their bow and you draw and throw a dagger a split second before their arrow gets into flight.</blockquote>