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I'm currently playing monk with Open Hand Technique. When I use Flurry of Blows how many attack rolls are made: one or two? If it needs two, does one hit trigger Open Hand Technique?

When I succeed at Flurry of Blows, Open Hand Technique says I can choose to push or knock the creature prone, but Flurry of Blows gives me two unarmed strikes. What happens if one of my attacks hits but the other doesn't?

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The Ki power Flurry of Blows, is very simple:

Immediately after you take the Attack action on your turn, you can spend 1 ki point to make two unarmed strikes as a bonus action.

Per Melee Attacks, an "unarmed strike" is a "melee weapon attack". Making an Attack includes three discrete steps, the attack roll is one of them.

Unless it says otherwise, multiple attacks are just that - multiple attacks, not a single attack that deals damage more than once. If there aren't two attack rolls, it isn't two attacks - it's one. Each attack must be rolled separately and hits or misses on it's own - anything that triggers off the hit (such as damage) is likewise resolved on its own. Extra Attack works the same way.

Way of the Open Hand's Open Hand Technique says:

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.

"Whenever" and "one of the" are the key bits of phrasing here. The two attacks don't have any effect on each other. If both attacks hit, you can inflict a different effect for each hit. In fact, you should resolve them individually and sequentially. If you knock the target prone, you have advantage on the next attack. If you knock the target away with the first attack, you need to use movement to make the second.

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  • \$\begingroup\$ Doesn't "one of the attacks" imply you can use this feature only once per Flurry? \$\endgroup\$ – enkryptor Oct 3 '17 at 20:22
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    \$\begingroup\$ @enkryptor No. "When you hit a creature with either" would mean one, "Whenever you hit a creature with one of the attacks" means both. "When either" can only happen once, "whenever one" can happen multiple times. Quite a few other abilities say "once per turn" or something similar. This one does not. \$\endgroup\$ – T.J.L. Oct 3 '17 at 20:23

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