D&D 5E When to Roll Initiative

By the time they react, they do know your party is there. As per Shield, you take the reaction when you are hit (or targeted by Magic Missile, which sets off your Spidey-senses). If you get them while they're still surprised they can't do that.

The assassin's party attack from an ambush. No one in the other group has sufficiently high passive perception to notice them, and therefore they are all surprised. Everyone rolls initiative. The other group (which might only be a single creature) rolls higher and goes first, followed by the assassin, followed by the rest of his party.

All of the opponents take their turns (doing nothing) and become able to react (ie, no longer surprised) by the time the assassin's turn comes up. Since none of the assassin's party has given away their presence, the other group shouldn't even know there is anyone to be fighting, much less have already become "unsurprised," but because of how initiative rolled the assassin has a nerfed assassinate in this situation. That's the situation I'm addressing.
 

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The assassin's party attack from an ambush. No one in the other group has sufficiently high passive perception to notice them, and therefore they are all surprised. Everyone rolls initiative. The other group (which might only be a single creature) rolls higher and goes first, followed by the assassin, followed by the rest of his party.

All of the opponents take their turns (doing nothing) and become able to react (ie, no longer surprised) by the time the assassin's turn comes up. Since none of the assassin's party has given away their presence, the other group shouldn't even know there is anyone to be fighting, much less have already become "unsurprised," but because of how initiative rolled the assassin has a nerfed assassinate in this situation. That's the situation I'm addressing.

Right. I understand the situation. They are able to take reactions before they are attacked. However, the first time they will take reactions is on the turns of their attackers, ie in response to an attack, so it's really not an issue of actually reacting to something that hasn't happened yet.

Before they are attacked, they don't know there is anyone to fight. They are surprised, so they "lose" their turns. The effect is that their attackers get to act first in the first round. Even though they have the higher initiative, they "lose out" on using their high initiative in the first round. Because they roll high on initiative, however, they have quicker responses than their attackers, and by the time the attack falls on them, they have shaken off their surprise and can react normally.
 

Yeah, and if it weren't for the fact that the assassin has a special ability that gets nerfed because of how it works, I'd probably just go by the book, and characters could just Dodge (or better yet, Ready something) if they wanted to a let an ally with a lower init be the one to initiate the ambush. Annoying assassin ability limitation.
 

Yeah, and if it weren't for the fact that the assassin has a special ability that gets nerfed because of how it works, I'd probably just go by the book, and characters could just Dodge (or better yet, Ready something) if they wanted to a let an ally with a lower init be the one to initiate the ambush. Annoying assassin ability limitation.

Yep. Makes the assassin a much less attractive class the way surprise works in 5E.
 


Only, ironically, against solo monsters. In a group there will always be someone to assassinate. Ironic because you'd expect an assassin to go after lone victims.

Doesn't a given assassin always have the same chance of rolling a higher initiative against a given opponent, no matter how many of them there are?
 

Doesn't a given assassin always have the same chance of rolling a higher initiative against a given opponent, no matter how many of them there are?

Sure. But if there are three opponents, you just need to roll higher initiative than one of them in order to use your ability, assuming you can tell when each of them "takes a turn" and shift your targeting accordingly. It's like double-disadvantage on initiative for the bad guys.
 

Only, ironically, against solo monsters. In a group there will always be someone to assassinate. Ironic because you'd expect an assassin to go after lone victims.

Depends on how you do initiative. I don't roll initiative for each individual monster. I roll for groups. If the group beats the Assassin, he can assassinate no one. It also depends on the location of the creature, if they are close enough to assassinate. It cheapens the ability. The class is less attractive because of it. I'd never recommend it at this point.
 

Sure. But if there are three opponents, you just need to roll higher initiative than one of them in order to use your ability, assuming you can tell when each of them "takes a turn" and shift your targeting accordingly. It's like double-disadvantage on initiative for the bad guys.

Hmmm, yes. The more non-identical creatures the more chances that someone will roll under your initiative. Ignoring Dex modifiers and how an individual DM might adjudicate ties then, does the probability of an opponent rolling under go up from 50%, with only one opponent, to 75% with two, to 87.5% with three, etc? If so that's pretty significant.
 

Hmmm, yes. The more non-identical creatures the more chances that someone will roll under your initiative. Ignoring Dex modifiers and how an individual DM might adjudicate ties then, does the probability of an opponent rolling under go up from 50%, with only one opponent, to 75% with two, to 87.5% with three, etc? If so that's pretty significant.

Then you have to take into account other factors. With non-identical creatures, are they all visible? Are some scouting? Are some built for initiative themselves? Does assassination feel satisfying if used on a weak minion? Non-identical creatures often mean enemy parties or an enemy party and a leader. That leads to a lot of variation in location. It's not as simple as the percentages you outline, at least not in my experience.

For example, last week I ran an encounter with a group of orcs, their orc chieftain, and a ranger.

Orcs might have lost initiative. Who cares? You don't even need a crit to kill an orc. Orc chieftain was hidden in cover. The ranger had pass without trace up and a high enough Stealth score the party couldn't see her. So even if you win initiative, if you don't see the target you can't hit the target. That's another strange effect from this ruling. The assassin could win initiative and still not be able to target someone that can't see him same as the target of his attack doesn't get to attack him until he sees him.

What would you do if the Assassin won the Stealth roll, was prepared to attack, lost initiative negating his ability to crit on surprise, then decide to not attack because he didn't win initiative? The target doesn't see him because he is hidden. So can he reset and roll initiative again since the target can't attack him because the target hasn't seen him? How do you work that by RAW? Nothing in the RAW states that the target even if he wins initiative knows the attacker is there until the attacker actually attacks. By RAW he could choose not to attack and stay hidden. Do you just roll initiative again next round or a few rounds later?
 
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