What is the proper use of initiative for a cautious encounter?

Question

I DMed a specific situation last night, and I'm not totally sure that I handled it in the right way.

For the last two sessions, the team has been facing off against a clever homebrew wraith (less mindless, more thoughtful, a little weaker to balance), who's moved to hit-and-run tactics. Frustrated, they tried to draw him out by talk, and he demanded they drop all their weapons and still their hands before he came out.

There were a couple of false starts when he ducked back out of sight when the rogue tried to hide some daggers, and again when the rogue cast a spell but was caught. Eventually he came out and they had a conversation - with him naturally on edge and waiting to dive out of sight, and with the party hands-up, talking, presumably also waiting for their moment.

The wraith was on top of a thirty foot temple roof, and they were standing on the stairs below, looking up at him. After some talk the cleric decided to take his shot with a spell (Guiding Bolt).

Based on the situation I let the wraith and the cleric roll opposed initiative to see if he got the spell off before the wraith ducked, but the rest of the party felt a bit cheated that they weren't included in that round.

My rationale was that not looking at each other, not having planned a trigger, having put the wraith on edge already, that they wouldn't all be aware that it was go time. Essentially the cleric caught them all off-guard because the cleric started casting without any sort of preamble, during other conversation.

I know it's not exactly normal surprise rules. How is this situation properly handled?

Answer 1

I think you handled that correctly. I generally handle such situations that whoever chooses to act first gets one action to start the conflict, then everyone rolls initiative, and we proceed from there. If someone else in the situation effectively had a "readied action" -- in this case, the wraith was clearly on edge, ready to duck at the slightest provocation -- that also gets resolved with the first action, then the initiatives all happen. This is not strictly RAW, but I find it to be the fairest and best method for such situations.

To clarify and elaborate a bit:

1. Everyone was on guard and aware of the opponents, so no surprise in this situation.

2. Although RAW you can only "ready" an action in combat, I do permit, in standoff situations like this, PCs and NPCs to declare an action and a trigger for that action, i.e. what they plan to do first if hostilities commence.

3. However, I prefer not to have everyone actually roll initiative until someone starts the hostilities with an action. I think that having initiatives already rolled tends to push the situation towards hostilities. It also gives the players too much information about what order things may happen in once the fight starts -- information the characters would not have. I like the feeling of uncertainty and unpredictability that a standoff has, without initiative being known beforehand.

So I like having the tension there, and maybe everyone holds off, or maybe someone starts it -- in which case the first action and any "readied" actions happen, then we roll initiative and go into it.

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I find a middle ground useful with regard to "readied" actions, in that it doesn't make sense for a person to have an action "readied" for long periods of time, but in brief situations that are tense, but where actual combat and initiative aren't needed, a "readied" non-combat action can make sense. Suppose, for example, a character is on a panicked horse, and fails to control it. We don't need to go into full combat, but it makes sense for the character to "ready" an action by stating that, say, "when the horse crosses the bridge, I'll jump off into the water". I see standoffs and ambushes the same way.

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"Acting first" doesn't actually mean going back in time and acting before someone who has just chosen to act. You can react super quickly; you can be the first to act after the triggering event, but no matter how high your initiative, you can't say "that bomb that just went off, well my initiative is higher, so I'm going to duck for cover just before it went off". In a standoff, everyone is intentionally standing off -- not acting -- until someone decides to act, and then that's the first thing that happens.

Answer 2

As with most things in the game it's ultimately the DM's call and personally I think you handled it rather nicely. But all the same let's have a look at the rules.

First off I don't think the normal surprise rules should come into play at all.

The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. [...] Any character or monster that doesn't notice a threat is surprised at the start of the encounter.

_{PHB, pg.189}

Given that everyone is already aware of everyone else then no one can/should be surprised.

Next there's the rules for initiative:

When combat starts, every participant makes a Dexterity check to determine their place in the initiative order.

_{PHB, pg.189}

There are no rules to say exactly when combat starts so again it's up to the DM to use their best judgment. However my rule of thumb in situations like this is that as soon as someone goes to make a move then combat is initiated, everyone rolls initiative and takes their turn on their initiative count as normal without any special "you made the first move so you get to act first regardless of your initiative roll".

Generally my players are pretty happy with this ruling but if there is an argument then the rationale can be given that (assuming the cleric doesn't roll the highest initiative) whichever character(s) do roll higher than the cleric see the cleric start casting and everyone "reacts" (non-game term) to the casting and starts doing their own combart thing.

Answer 3

The rules are pretty unambiguous here:

...the GM 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.

If you’re surprised, you can’t move or take an action on your first turn of the combat, and you can’t take a reaction until that turn ends. A member of a group can be surprised even if the other members aren’t.

In this case, everybody was aware of at least one threat, so nobody was surprised and everyone should have been able to participate in any combat rounds that happen.

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Frequently, in cases like yours, people find these rules unsatisfactory. What if everyone kind of knows a combat might break out, but nobody knows exactly when that's going to be? Maybe some subgroup of the combatants should get an advantage by declaring they're throwing the first punch?

It's a common house rule. But the rules say it doesn't work like that.

Answer 4

In this case it should be fairly clear. There was no surprise, as everyone was ready to go.

As soon as the cleric starts casting a spell everyone rolls initiative. Everyone moves when their initiative is reached.

That's it, that simple.

If the wraith rolled higher than the cleric then it saw him start casting the spell and acted before he could finish it. If the cleric rolled higher then he managed to cast the spell before the wraith got out of sight.

The only way a surprise round would come into play was if the cleric was somehow hidden or concealed from the wraith (which might include somehow hiding what he was doing such as if he managed to cast the spell silently and without moving).

Answer 5

There should not have been any roll involved, probably

I would have handled this as a readied action. The wraith has demanded they put up their hands, drop their weapons, and not move. I would take that as having a readied action to (do X, probably run into the wall), as soon as anyone moved their hands. Guiding Bolt has a somatic component, like 99% of hostile spells, so the cleric should have had to move before casting the spell (I assume 'hands up' interferes with somatic components at least as much as holding a sword and shield. You need a free hand to cast and a hand isn't free if it's being held up above your head as a sign of surrender). Thus, as soon as the Cleric took their hand down to go start casting, the wraith should have interrupted their turn and left.

If the wraith sticks around, combat should go as normal

If combat happens at all (i.e. the wraith doesn't use a readied action to flee before anyone can do anything) then everybody should roll initiative normally and go as normal. Nobody's surprised, and the Cleric who broke parley doesn't get any special treatment for being the one who threw law, custom, and honor to the wind for a potential bit of damage, though it would not be unreasonable to grant them advantage on their initiative roll.