D&D 5E Actions and When to Enter Initiative

If anyone starts to cast a spell or attack initiative is rolled. Combat rounds are over in seconds in game time, the fact that it may take a few minutes is just there because we can't process multiple simultaneous actions in a PNP game.

I assume that starting to cast a spell is always the same, by the time it gets to the initiative of the caster they can change their mind.

There are exceptions of course where some or all of the participants will be surprised the first round. The rogue may try to pull the dagger with a sleight of hand, the sorcerer may have silent stilled spells and so on.
 

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I call for initiative any time there is uncertainty as to the order of events. When one character acts and another character wants to interrupt that action, Initiative is rolled to determine who gets to act first. I hadn’t considered giving Advantage or Disadvantage on what is effectively a contested Dexterity vs. Dexterity check, but I like the idea a lot and might chew a bit on when it might be appropriate to apply them.
 

Both case roll initiative. They are both situation where every opponents are on their guard.

In a more relax situation a deception vs insight can be use to gain surprise or advantage on initiative.

But Features like subtle casting can lead to different interpretation. Maybe give insight with disadvantage to avoid being completely surprised.

Rule of thumb.
Players don’t like to get fooled without at least a roll.
Any threatening action should be described by everyone with a “preparation step” before resolution. Start casting, draw weapon, aim, etc...
it let more space to allow reaction or engage fight.
 

I usually roll init & use Deception vs Passive Insight to not be Surprised in this sort of situation. Of course a PC with Alertness won't be Surprised. And a Barbarian might Rage & act first though Surprised.

If I don't want to use the formal combat system for some reason then I'll wing it, but still probably looking at use of skills like Sleight of Hand & Deception vs Passive Perception or Passive Insight.

Advantage on Init I'll use for cases where one side is 'ready', and the other side is alert but not specifically ready. Eg when the stormtroopers blow the door at the start of Star Wars & come in, I'd give the prepared Rebel/Senatorial troops advantage on init roll to shoot first.
 

If a PC wants to pull off a surprise move I'll give the target a surprise check (more or less difficult depending on the situation) and bystanders a general-but-difficult perception check; if the target's surprised the PC action tries to happen (an assassination attempt, for example, would still need an attack roll) before anything else is done.

Then, if anyone other than the target wants to react they have to make surprise rolls to determine how badly (if at all) the sudden action caught them off guard, or have succeeded on the perception check earlier. Those who aren't surprised, plus the aggressor and the target, then get initiative. Those who are surprised either get initiative with a penalty or get punted to the next round, depending how bad the surprise roll was.

Same holds true if it's an NPC (or another PC!) trying something sudden against a PC: the PC gets a surprise check and if it fails the PC's likely in trouble. This comes up fairly often, be it via a possessed or dominated PC suddenly turning against the party, or their having a doppelganger in their midst, or simple PvP.
 

I call for initiative any time there is uncertainty as to the order of events. When one character acts and another character wants to interrupt that action, Initiative is rolled to determine who gets to act first. I hadn’t considered giving Advantage or Disadvantage on what is effectively a contested Dexterity vs. Dexterity check, but I like the idea a lot and might chew a bit on when it might be appropriate to apply them.

I also use initiative to resolve uncertainty. I would note that the converse is also true: when there is no uncertainty as to the order of events, I don't roll initiative. So if only one PC/NPC wants to act, they simply go first. If, as a consequence of that action, others then want to act, they go afterwards (rolling initiative if there is more than one of them).
 

I'm curious how other DMs handle the situation where you're in free roleplay, not combat initiative, and then someone does something that someone else might want to stop.

Recent situations that got me thinking about this:

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.

2. In another game where I was the DM, the PCs had tracked down a suspicious spellcaster and were threatening him. The NPC wanted to get out of the situation, so he started to cast greater invisibility on himself. The players instantly asked if they could interrupt the spell, and so I had them all roll for initiative. (The spellcaster wound up going last, so by the time his turn rolled around, there was basically no way he could escape.)

It seems like these are very much the same situation, but flipped around. The DM could easily have made my PC roll for initiative in the first instance, but didn't.

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"?

*custom spell for the setting.

Have them roll perception / insight / whatever. A failed roll would give surprise, which guarentees acting first. Since it's a single action, we don't need to bother to roll initiative because it's over after that. (Assuming it would be over.)
 

I'm curious how other DMs handle the situation where you're in free roleplay, not combat initiative, and then someone does something that someone else might want to stop.

Recent situations that got me thinking about this:

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.

2. In another game where I was the DM, the PCs had tracked down a suspicious spellcaster and were threatening him. The NPC wanted to get out of the situation, so he started to cast greater invisibility on himself. The players instantly asked if they could interrupt the spell, and so I had them all roll for initiative. (The spellcaster wound up going last, so by the time his turn rolled around, there was basically no way he could escape.)

It seems like these are very much the same situation, but flipped around. The DM could easily have made my PC roll for initiative in the first instance, but didn't.

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"?

*custom spell for the setting.
In cases where it's not surprise but at least unexpected, I tend to give the initiator advantage on initiative. The rest roll normally and the intent "casting a spell" is known for those with eyes on the target.

If the initiator sets things up with a distraction or deception, they might get surprise.
 

A couple of things might help your understanding.

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.

Initiative determines the order actions are resolved, not started
It does not decide when characters start actions; it decides when those actions are resolved. 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.

Conan has kicked off the fight by swinging at the priest, but normal initiative rules still apply. Surprise might apply - the priest might not have noticed Conan's actions (a Charisma\Deception roll probably needs to be made).
 

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.
 

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