D&D 5E Actions and When to Enter Initiative

Interesting idea.

Do you always roll both? Does the order of the rolls matter? I.e., if the instigator wins intiative, does it matter whether the others are surprised? Does the instigator get a free round in that case and then get to act again immediately?
OH I FORGOT AN IMPORTANT PART:
When the instigator gets advantage on their initiative check, they can't change their action when their turn comes up; they MUST take the action that initiated the combat. That may seem obvious, but it's another subtle reason why the system favors the instigator: they are trading the ability to select their action on their turn, for the likelyhood of going first.



The order of the rolls doesn't matter. I usually do initiative first so that I can put my little stand-up things in order. Then, anyone who fails surprise, gets their stand-up knocked over.

Sometimes I don't roll for surprise if it's clear that literally everyone is expecting someone to blink first, like in a Mexican stand-off.

Other times, I give advantage/disadvantage on the surprise portion. For example, the players will tell me that they're watching out for betrayal, so they get advantage to not be surprised.

Certain players try to "Ready" an action while out of combat, which I don't allow. But IF the trigger comes to pass, I'll usually give advantage to not be surprised and advantage on initiative, but the character MUST take the "Readied" action on their turn. Because I think successfully predicting a trigger should help you go first, but it shouldn't be automatic. It's kind of similar to the reasoning that gives the instigator advantage by restricting their action.
 

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So how do other people handle these situations? Do you always go with what makes things easier for the PCs? Is there a more graceful way of handling situation #2? Is there any way of having NPCs take PCs by surprise that won't leave the players shouting "That was cheap"?
In rare situations I will ask players to roll initiatives even though there is no combat happening, and I do that just to be able to deal with their actions one at a time in some kind of order. However, as a rule, if I call for initiative it is for one reason - COMBAT has commenced for one reason or another.

The FIRST individual to state they are taking a combat action is at the top of the order. If anyone else was anticipating the possibility that the individual MIGHT take an offensive action they darn well should have SAID SO. That would be the Ready action - specifically preparing a response that COULD interrupt someone else's intended action. That is, the readying character gets to go first and gets to do their own clearly stated and planned thing, and then we see if that prevents the first individual from completing their instigating action. So people who simply STATE they will do X, and people who STATE they are PLANNING to do Y if person Z does X, are the ones who go first. Everyone else rolls initiative.

Complaints? Take a number. Your initiative result determines that number. Want to be sure your character gets to do something first? Be the first to say you're doing something. Waiting to see what happens without making clear and specific plans? Luck of the dice determines your readiness to act/react - but only AFTER people who have made positive statements of action. Should it become necessary to prioritize further, then the order in which people make their statements determines the order of the priority of their actions: first-stated, first-resolved.

Surprise is a mechanic used to begin combat. If I, as DM, decide that one SIDE is surprised (the two sides always being PCs on one side, and their opponents on the other) then they are. The non-surprised side then get one free round to act while the other side gets up to speed with what's actually happening. If I, as DM, decide that neither side is really going to be caught unwares, then neither side IS caught unawares and there is no surprise resolution, and initiative alone determines order of actions. If I, as DM, decide that either side COULD be surprised, but don't care to make that determination myself (and there can be any number of reasons for that), then surprise rolls are made that will determine it instead.

Fair means of having NPC's take PC's by surprise? Same means that PC's have of taking NPC's by surprise, however, I use those means with FAR greater restraint than I ever expect PC's to do. If the DM wants to win - he wins. If the DM wants PC's to die - they die. WINNING, for a DM, is as easy as breathing. But that's not exactly a recipe for a fun, satisfying game for players to play. Can PC's be ambushed? Of course. And if I ambush them I will have provided clues, hints or even openly stated warnings - and if players then fail to take precautions that's on them.

My aim is to never hear players shout, "That was cheap!" after being ambushed. My aim is for players to have their characters ambushed and after the battle is over shout, "That was EXCITING!"
 

For eg. I have even seen a situation where a player wishes to shoot a distant enemy with an arrow and a DM calls for initiative early. Resist that urge. Let the PC fire, THEN roll initiative.
Based on my understanding of the rules as written in 5E, this is how it is supposed to play out:
1) Player character wants to shoot an enemy with an arrow.
2) DM decides enemy is surprised.
3) DM calls for initiative rolls.
4) During the first round, the enemy skips their turn because they are surprised, therefore the PC shoots first even if they didn't win initiative.
5) If the PC did win initiative, they act first in the second round, effectively getting two turns in a row. Huzzah!

So technically, you should roll initiative before the PC shoots, but the PC is still gonna shoot first.
 

Based on my understanding of the rules as written in 5E, this is how it is supposed to play out:
1) Player character wants to shoot an enemy with an arrow.
2) DM decides enemy is surprised.
3) DM calls for initiative rolls.
4) During the first round, the enemy skips their turn because they are surprised, therefore the PC shoots first even if they didn't win initiative.
5) If the PC did win initiative, they act first in the second round, effectively getting two turns in a row. Huzzah!

So technically, you should roll initiative before the PC shoots, but the PC is still gonna shoot first.

Right. There's a 5-step "Combat Step by Step" sidebar right in the beginning of Chapter 9. Really easy to see what to do by following it in my view.

Knowing when to call for ability checks helps too.
 

The FIRST individual to state they are taking a combat action is at the top of the order. If anyone else was anticipating the possibility that the individual MIGHT take an offensive action they darn well should have SAID SO. That would be the Ready action - specifically preparing a response that COULD interrupt someone else's intended action. That is, the readying character gets to go first and gets to do their own clearly stated and planned thing, and then we see if that prevents the first individual from completing their instigating action. So people who simply STATE they will do X, and people who STATE they are PLANNING to do Y if person Z does X, are the ones who go first. Everyone else rolls initiative.
The practical result of such a system, in my experience, is that everybody is always declaring they're readying an action all the time. It gets very tiresome. I find it more convenient to take it as a given that in a typical adventure-y type situation everybody is on their toes and ready for danger, and use the initiative system to determine who is the most ready for danger at any given moment. If somebody isn't ready for danger, that's what the surprised condition is for.

Come to think of it, I've mentioned the surprised condition three times now in as many posts. Do other people not use that rule or something?
 

The practical result of such a system, in my experience, is that everybody is always declaring they're readying an action all the time. It gets very tiresome.
Only, in my experience, when the DM allows them to choose what to actually do in the moment anyone does anything they decide they don't want them to do. Saw that a lot with 3E.

"I ready to attack".

Okay, do you ready to attack with a sword or your bow? Can't do both. Pick one. Do you ready to attack if the enemy casts a spell or if he pulls out a wand? Can't do both. Pick one. Choose a specific action to perform; choose a specific trigger for that action. THAT is readying. It has limited usefulness. If players want to constantly ready actions then others who actually ACT should constantly leave them standing about looking dumb. Certainly while combat is taking place, 99% of the time readying an action should be a waste of time. Waiting for an opponents turn and for their actions to trigger yours is ridiculous if you can just act against that enemy NOW.
 

Initiative is not just for combat
Initiative is for any situation where timing matters. Most of the time, this is actual combat, but not always.
Very true, though keep in mind that oftentimes in non-combat situations the usual modifiers to initiative might not apply - you're basically just rolling unmodified dice to see what event happens first (or, if the dice are tied, whether they occur at the same time).

Initiative determines the order actions are resolved, not started
It does not decide when characters start actions; it decides when those actions are resolved.
You know, I'd never really given any serious thought to this before now, but since forever I've always kind of seen initiative as being when your action - wait for it - initiates. Largely a moot point in 5e where most actions initiate and resolve at the same time, but for movement in particular I've always had it that your init is when you start moving, not when you arrive (and movement isn't a mini-teleport, it takes time to get from A to B even though the rules-as-written have completely ignored this since before 3e).

If Conan has attacked the priest in the middle of conversation then the priest still has a chance to resolve an action before Conan. Conan's actions are not instantaneous.
But neither are the priest's, so it will (or should!) come down to first in, first out - the priest will still be undertaking his action when Conan's fist connects with his jaw.

Now if the priest noticed something amiss ahead of time and in fact started an action first, that's different; and then it's Conan who's probably on the receiving end.
 

Only, in my experience, when the DM allows them to choose what to actually do in the moment anyone does anything they decide they don't want them to do. Saw that a lot with 3E.

"I ready to attack".

Okay, do you ready to attack with a sword or your bow? Can't do both. Pick one. Do you ready to attack if the enemy casts a spell or if he pulls out a wand? Can't do both. Pick one. Choose a specific action to perform; choose a specific trigger for that action. THAT is readying. It has limited usefulness. If players want to constantly ready actions then others who actually ACT should constantly leave them standing about looking dumb. Certainly while combat is taking place, 99% of the time readying an action should be a waste of time. Waiting for an opponents turn and for their actions to trigger yours is ridiculous if you can just act against that enemy NOW.

While a quibble fest over how precise s trigger csn snd csnnot be eould be pointless since its GM csll, I will say that Ready in combat is far from ridiculous if used well.

Timing and coordination is more important than "now".
 

In a situation like #2, it's pretty clear that the PCs would be invested in stopping him from casting the spell, so I'd just say, "He tries to get a quick spell off. Roll initiative."
Where I'd say something more like "Roll to see if you notice something" without saying what, as if they blow the roll the first thing they'll actually notice is when the guy vanishes - and they might not know how he did it (spell? device? was he an illusion all along?). If they notice he's casting a spell then initiative applies, though here's where some dumb 5e rules really get in the way: because the PCs actions can't start until they've noticed the spell being cast (because that's the trigger for the actions), by the time they can do anything the spell will have resolved as 5e doesn't have spells take any time at all to cast.
 

Initiative is always there. There is never a point where the players aren't acting under initiative.

However, most of the time it doesn't matter much. We roll for initiative when the order that characters are taking actions matters.

Actually, looking up a bit, two posts above mine Greenstone.Walker has well covered all the issues already, so I'll just stop here.
 

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