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Do "on-hit" effects which allow you to push a creature backwards get decided immediately when you roll the hit? Or after all attack rolls are made for multiattacks? If you have to decide immediately upon finding out the roll is a "hit", can pushing an enemy back with the first hit immediately push them out of range for a second hit, or do these push effects take place after all hits are resolved?

An example: An open hand monk attacks two times with a flurry of blows. They roll the first attack, and it hits; do they now have a dilemma deciding whether to apply the push effect knowing it will put them out of range for the second hit?

Context: Building a Open Hand, Swarmkeeper, Battle Master which could potentially stack push effects

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The effect takes place immediately

Note: This answer only considers the named features that you mentioned in your question, Flurry of Blows and Open Hand Technique. There are a lot of features that apply Shove in 5e and the answer will vary depending on their wording so I’m specifically considering the wording of just these two here.

The attacks that you make happen consecutively, one at a time, not all at the same time. Therefore they also get resolved consecutively; the consequences of an attack get applied before you make your next attack.

From the Open Hand Technique feature:

(…) Whenever you hit a creature with one of the attacks granted by your Flurry of Blows, you can impose one of the following effects on that target (…)

The effect happens when you hit with an attack; it doesn’t say that there’s a delay involved or that it takes effect after you have made all your attacks, etc. Therefore, the effect occurs immediately after you make an attack and hit.

Flurry of Blows states:

(…) you can spend 1 ki point to make two unarmed strikes as a bonus action.

Each of the unarmed strikes that the feature lets you make is a separate attack which requires a separate attack roll - they happen and get resolved consecutively. An effect that takes place on a hit will happen immediately after it; if the first attack is a hit, the effect will happen in between the first and second attack.

So in your example, yes, if you hit with the first strike in a Flurry of Blows and decide to push the enemy away, it will be pushed immediately and end up out of your range for your second attack.

Extending this answer to the features that you’ve listed in comments - they are both worded in a similar way to the Open Hand Technique and would function in the same way:

Gathered Swarm: Once on each of your turns, you can cause the swarm to assist you in one of the following ways, immediately after you hit a creature with an attack: (…)

This feature goes further by explicitly stating that the effect happens immediately after you hit.

Pushing Attack: When you hit a creature with a weapon attack, you can expend one superiority die to attempt to drive the target back. You add the superiority die to the attack's damage roll, and if the target is Large or smaller, it must make a Strength saving throw. On a failed save, you push the target up to 15 feet away from you.

Again, this takes effect when you hit a creature. The maneuvers are worded in a way that is very precise about the circumstances in which they can be used. The fact that the creature gets a saving throw here is immaterial in this context; all it means is that the effect doesn’t happen automatically. The save is resolved at the same time as the damage of the attack, and then you make the next attack.

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    \$\begingroup\$ end up out of your range for your second attack. - unless you spend 5 feet of movement, of course. It's a valid option to not wait until the last attack (which might miss) if the important thing is that they move relative to other things, not that you finish your attacks not being adjacent (free disengage). Edit: Chris already posted an answer pointing this out. \$\endgroup\$ Commented Aug 7, 2022 at 5:04
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    \$\begingroup\$ @PeterCordes sure, if you still have movement left you can spend it to get close again for your next attack, that happens after the first attack and its effects get resolved though \$\endgroup\$
    – AnnaAG
    Commented Aug 7, 2022 at 20:55
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Yes, a push caused by an attack happens immediately after that attack — which is explained better than I could hope to in AnnaAG's answer. I'd just like to clear up a possible hidden assumption in the question.

A character can move between their attacks.

Moving Between Attacks

If you take an action that includes more than one weapon attack, you can break up your movement even further by moving between those attacks. For example, a fighter who can make two attacks with the Extra Attack feature and who has a speed of 25 feet could move 10 feet, make an attack, move 15 feet, and then attack again.

Basic Rules, Chapter 9

Now it's entirely possible that the monk in the question has no movement left — maybe they used it all getting into position for their first attack — but in general, if a character pushes their target on their first attack, they can move to close the distance and continue attacking.

And bonus actions — e.g., Flurry of Blows, which lets a monk make two additional attacks — are actions, so the above rule applies to those attacks as well.

Bonus Actions

Various class features, spells, and other abilities let you take an additional action on your turn called a bonus action.

Basic Rules, Chapter 9

So in one turn, a 5th level monk of the Way of the Open Hand with Flurry of Blows, Extra Attack, and +10 ft of Unarmored Movement could:

  1. Move 5 ft;
  2. Use the Attack action and make an attack;
  3. Move 5 ft;
  4. Make another attack against a second target;
  5. Move 5 ft;
  6. Use the Flurry of Blows bonus action and make another attack against a third target;
  7. On a hit, push their target 15 ft;
  8. Move 15 ft;
  9. Make another attack against that target;
  10. On a hit, take away their target's reaction until the end of their next turn;
  11. Move back 10 ft.

Monks in D&D 5e are ridiculously mobile.

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    \$\begingroup\$ This would be better as a standalone answer IMO, even if it risks duplicating information. Otherwise it doesn't answer the main question by itself. \$\endgroup\$ Commented Aug 7, 2022 at 10:39
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    \$\begingroup\$ @AncientSwordRage: One way to write answers like this is to briefly state the conclusion, and refer readers to another answer for the reasoning. So that part stays one short paragraph, but does actually answer the question. Then the answer can move on to topic it wants to cover. \$\endgroup\$ Commented Aug 8, 2022 at 1:07
  • \$\begingroup\$ There's several was to answer a question, but I don't think this is a good one. \$\endgroup\$ Commented Aug 8, 2022 at 13:10
  • \$\begingroup\$ @AncientSwordRage Fair point. I've added a fig leaf of an answer to the explicit question, which I hope is enough. I'd like to keep the focus on what I feel is the implicit question: Can my character keep attacking if they push their opponent? \$\endgroup\$ Commented Aug 9, 2022 at 14:41
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    \$\begingroup\$ @JordiVermeulen The bit I quoted covers that. A character can move between any attacks during an action, not just those from the Attack action. Bonus actions are actions — I should clarify that in the answer. \$\endgroup\$ Commented Aug 18, 2022 at 0:35
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You only make 1 attack at a time

You probably saw people on Critical Role or something rolling all their attacks together. This is a common house rule but it's not RAW. The rules say you should resolve each attack one at a time, not simultaneously.

https://www.dndbeyond.com/sources/basic-rules/combat#MakinganAttack

Whether you're striking with a melee weapon, firing a weapon at range, or making an attack roll as part of a spell, an attack has a simple structure.

  1. Choose a target. Pick a target within your attack's range: a creature, an object, or a location.

  2. Determine modifiers. The DM determines whether the target has cover and whether you have advantage or disadvantage against the target. In addition, spells, special abilities, and other effects can apply penalties or bonuses to your attack roll.

  3. Resolve the attack. You make the attack roll. On a hit, you roll damage, unless the particular attack has rules that specify otherwise. Some attacks cause special effects in addition to or instead of damage.

So the process is as follows;

  1. Monk spends 1 qi to activate Flurry of Blows
  2. Monk makes the first attack;
    1. Choose a target within range
    2. Determine modifiers
    3. Resolve attack
      1. Roll hit - let's assume it hits
      2. Since it hits we can activate Open Hand Technique, the target fails the save and is pushed back 15ft
      3. Roll the damage
  3. The monk can now make the second attack. However before you make the attack you might want to take this opportunity to move to a target since your previous target just got pushed back and may be out of your reach.
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