D&D 5E Actions and When to Enter Initiative

The orc-and-elf example has one slight problem: both are most likely expecting things will - or very much could - end in bloodshed; meaning both are almost certainly ready for battle and each is highly unlikely to be caught off guard by the other.

The situations we've otherwise been talking about, however, don't include this factor. If I'm playing an Assassin, for example, and my unsuspecting target is at a garden party to which I've also been invited, the target isn't likely to be ready for battle when I slide up beside him and sink my shiv into his side. This is the sort of situation that brings about the when-does-iniative-start questions - does it start before I attack, when I attack, after I attack, or not until later when someone notices the attack has occurred (by which time I might not be around to further participate, having made good my escape)?
 

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1. In a game where I was a player, my character was trying to infiltrate a secure area. When her bluff attempt failed, she was placed in a room with guards while the guy who caught her went to get the boss. She used a spell that allowed her to turn into shadow* and escaped.

I would have asked how your character was hiding that she was casting a spell from the guards. If there was no special thinking behind it, I would have asked for you to roll a Deception check vs. the guards' Insight check. If you succeeded, you would surprise them and cast your spell without issue (technically initiative would be rolled first, but would be irrelevant since you'd have surprise round and not worth bogging things down). If you failed, initiative would be rolled as normal...if you rolled lower initiative, the guards would attempt to grapple or subdue your PC to prevent her from spellcasting.
 


I would have asked how your character was hiding that she was casting a spell from the guards. If there was no special thinking behind it, I would have asked for you to roll a Deception check vs. the guards' Insight check. If you succeeded, you would surprise them and cast your spell without issue (technically initiative would be rolled first, but would be irrelevant since you'd have surprise round and not worth bogging things down). If you failed, initiative would be rolled as normal...if you rolled lower initiative, the guards would attempt to grapple or subdue your PC to prevent her from spellcasting.

Ding. Ding.
 

First of all, we're not talking about what occurs while combat is taking place. We're talking about what occurs at the beginning of combat, when acting against an enemy "NOW" may be impossible or impolitic.
In which case, if we're not talking about when combat is taking place, there isn't a real need for initiative. Initiative rolls are a random determination of who goes first. Adjustments may apply but it's still random. When talking about about how you DO initiate combat without then suddenly being subject to random determination, just be the first one to state you ARE acting. That gets you to top of the order in my games. When commencement of an action is conditional upon someone else's action, then usual rules regarding Readying actions would apply, but SOMEONE begins the chain reaction, and as I said, first to say they act, acts first. When the situation is one of general, simultaneous commencement of hostilities, then random rolls are appropriate.

Secondly, your attempt to add nuance just adds fiddliness to the adjudication, takes up even more time, and generally adds an adversarial element to the exchange between player and DM.
Never has for me. It was a solution to the problem of abuse of Readying (at least in pre-5E games where Readying was a thing).

"I move down the hallway and ready an attack if there is a hostile creature." "Okay, do you ready to attack with a sword or your bow? What action are you readying against? How far do you move? Etc." "Fine: I move 30 feet down the hallway and ready my bow to shoot the first hostile creature who appears within range of me." Do you want your players doing that every 30 feet of every hall?
Nope. And they don't want that either. Besides which, if you're moving down the hall you're not readying, you're moving down the hall. If they want to state they are moving down the hall and are expecting to see opponents to shoot, and have reason to expect that to happen rather than just taking a guess that it might happen, then I have no problem giving them initiative, rather than rolling for it. In a specific circumstance where they have reason to expect to suddenly see opponents to shoot, and state that they proceed on that expectation, they're doing things properly and don't need to Ready anything. If they have no reason to expect to see opponents to shoot as they move down the hall, but want to try to READY to shoot just in case they do, that flat out won't work.

The alternative I humbly propose is to assume in good faith that competent adventurers are behaving this way, offload the burden of determining who draws first onto the game system that was designed for precisely this purpose, and get on with exploring the dungeon.
I do assume in good faith that competent adventurers (and players) are at all times attempting to be aware, prepared, and willing to act instantaneously as necessary. They attempt it always by MY default assumption as DM. But no amount of tedious attempts to become impossible to catch off guard, or to always act first by constant, never-ending Readying is going to work, effectively because Readying doesn't work that way, nor for that purpose, and I think I'd be a poorer DM if I let it be.

But as far as the game is largely concerned, initiative is always random. That's a problem. It prompts questions as we see in the OP - how DO you catch someone off guard without initiative determination then getting in the way. I'm saying that while most occasions where initiative gets involved it IS randomly determined, there are also many situations where ASSIGNING initiative is more appropriate. Like when everyone is in a standoff and someone finally says, "Enough of this. I ATTACK," or, "My PC runs and dives for cover." That character gets top of the initiative order. Not advantage on the roll or additional bonuses. He goes first because that is appropriate in the situation, and random determination of his order in initiative would not be. That is not BTB rules, of course. It's my way of handling the issue, which is what I believe was requested.
 

In which case, if we're not talking about when combat is taking place, there isn't a real need for initiative. Initiative rolls are a random determination of who goes first. Adjustments may apply but it's still random. When talking about about how you DO initiate combat without then suddenly being subject to random determination, just be the first one to state you ARE acting. That gets you to top of the order in my games. When commencement of an action is conditional upon someone else's action, then usual rules regarding Readying actions would apply, but SOMEONE begins the chain reaction, and as I said, first to say they act, acts first. When the situation is one of general, simultaneous commencement of hostilities, then random rolls are appropriate.

Never has for me. It was a solution to the problem of abuse of Readying (at least in pre-5E games where Readying was a thing).

Nope. And they don't want that either. Besides which, if you're moving down the hall you're not readying, you're moving down the hall. If they want to state they are moving down the hall and are expecting to see opponents to shoot, and have reason to expect that to happen rather than just taking a guess that it might happen, then I have no problem giving them initiative, rather than rolling for it. In a specific circumstance where they have reason to expect to suddenly see opponents to shoot, and state that they proceed on that expectation, they're doing things properly and don't need to Ready anything. If they have no reason to expect to see opponents to shoot as they move down the hall, but want to try to READY to shoot just in case they do, that flat out won't work.

I do assume in good faith that competent adventurers (and players) are at all times attempting to be aware, prepared, and willing to act instantaneously as necessary. They attempt it always by MY default assumption as DM. But no amount of tedious attempts to become impossible to catch off guard, or to always act first by constant, never-ending Readying is going to work, effectively because Readying doesn't work that way, nor for that purpose, and I think I'd be a poorer DM if I let it be.

But as far as the game is largely concerned, initiative is always random. That's a problem. It prompts questions as we see in the OP - how DO you catch someone off guard without initiative determination then getting in the way. I'm saying that while most occasions where initiative gets involved it IS randomly determined, there are also many situations where ASSIGNING initiative is more appropriate. Like when everyone is in a standoff and someone finally says, "Enough of this. I ATTACK," or, "My PC runs and dives for cover." That character gets top of the initiative order. Not advantage on the roll or additional bonuses. He goes first because that is appropriate in the situation, and random determination of his order in initiative would not be. That is not BTB rules, of course. It's my way of handling the issue, which is what I believe was requested.
I think it's safe to say that your house rules or rulings on readying etc seem to be getting you what you seek but are as you say solutions to issues from previous editions.

I think extending that to the broader view of 5e init is a stretch.

As I and others have observed, use of deception to gain distraction and surprise allows the caster in the OP case to start and finish their action without interruption. Failing to surprise, it becomes a random event, but they may still get advantage on that init check if the plan was good but did not succeed outright.

None of that is outside the 5e rules - so I dont see them as "the problem" in the OP example.

But that's me.
 

You have already received some good supplies. If action is started AND others recognise/see this and try to interrupt then yeah, give the initiator advantage.
What I see with initiative with some groups is the rolling of initiative BEFORE anything has happened. Such as a DM wanting one of the monsters to take an action so then asking to roll initiative. This to me is a mistake. Just do the action. IF a PC recognises/sees this then allow initiative (again with initiator getting advantage). Initiative should occur AFTER the initial action that LEADS to combat.
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.

That isn't how the game is designed.

Note, I'm not saying you can't play that way, I just think it's bad advice.

Everyone wants to be the one to act first. Initiative helps to be cinematic and have dramatic and tension filled scenes. In my fantasy/action movies I like to imagine that both sides of a conflict want the upper hand. That tension is great, knowing the outcome ahead of time deflates that.

It's not fun to be attacked and not be able to do anything about it. Acting outside of combat is essentially super surprise (as the enemy doesn't even get a chance to use a reaction). PCs and other creatures just shouldn't be surprised if they are aware of their enemies.

I don't think I would want to play at a table where the first person to shout gets to do the thing.

To put it another way -

Greedo declared his action first but Han won initiative.
 

The orc-and-elf example has one slight problem: both are most likely expecting things will - or very much could - end in bloodshed; meaning both are almost certainly ready for battle and each is highly unlikely to be caught off guard by the other.

The situations we've otherwise been talking about, however, don't include this factor. If I'm playing an Assassin, for example, and my unsuspecting target is at a garden party to which I've also been invited, the target isn't likely to be ready for battle when I slide up beside him and sink my shiv into his side. This is the sort of situation that brings about the when-does-iniative-start questions - does it start before I attack, when I attack, after I attack, or not until later when someone notices the attack has occurred (by which time I might not be around to further participate, having made good my escape)?

In large part this is because we are using the wrong scores to determine initiative. So in Pathfinder 2 this would be resolved by your sneaky bugger rolling Stealth for initiative and the unsuspecting target rolling Perception probably with a circumstance penalty for being distracted. If your roll beats their passive perception they would not realize you are there although they might look around if they have reason to suspect something.
 

@Man in the Funny Hat @Lanefan @everyone-else-who-thinks-there-is-a-problem-in-need-of-a-solution-here ---

"Any character or monster that doesn't notice a threat is surprised at the start of an encounter. If you're surprised, you can't move or take an action on your first turn in the combat, and you can't take a reaction until that turn ends. A member of a group can be surprised even if other members can't." (PHB 189)

Can you explain why you think this doesn't provide you with the necessary tool for resolving "got the drop on 'em" situations?
 

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.
5e spells do take time to cast, just as moving 30ft carefully, or attacking someone 1-5 times takes time.
These actions are resolved instantaneously, during the character's turn, but it is assumed that they still take time to perform.

So initiative begins when the spell starts to be cast, the sword-swing begins, or the opponent starts turning away to run. An opposed ability check (Wis(Notice) vs Dex(Stealth) or Wis(Insight) vs Cha(Deception) are common examples) determines surprise.
The whole "first character to begin doing something gets their action off first situation" is determined by the surprise system. Although I do understand it can be tricky to get the head around the concept that the first to declare "I draw my sword, move up and attack" might not be at the top of initiative - they are probably going first because everyone else is surprised and so can't act even if they did get higher initiative.

For an opposite example, imagine a scene where Bruce Lee is facing off against an opponent. The opponent starts to swing - and Bruce darts in and punches him before it connects. Bruce was not surprised, and even though his opponent declared their attack first, Bruce won initiative.

(There are always going to be edge 'what if' cases however. - an invisible flying opponent casts a subtle spell at a PC in magical darkness and a silence field - or similar. That is why the DM gets final say as to what happens when, and how it is resolved.)

The situations we've otherwise been talking about, however, don't include this factor. If I'm playing an Assassin, for example, and my unsuspecting target is at a garden party to which I've also been invited, the target isn't likely to be ready for battle when I slide up beside him and sink my shiv into his side. This is the sort of situation that brings about the when-does-iniative-start questions - does it start before I attack, when I attack, after I attack, or not until later when someone notices the attack has occurred (by which time I might not be around to further participate, having made good my escape)?
Initiative begins OOC when you declare the attack, and IC when your Assassin begins the strike. The target (having determined to be unsuspecting, probably by an opposed roll) is Surprised, and so even if they realise something is up at the last moment, cannot act during the first round in which you are stabbing them.
 

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