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While playing 5e with my playgroup, I made a staff strike, along with Flurry of Blows with my monk going for the extra 2 unarmed strikes. For this, my DM made me take a total of 2 attack rolls, one for the staff strike, and one for the "bonus action/attack." I failed the second roll, and was told that both of my unarmed strikes miss the target.

Now this made sense at the time, because I assumed that the two strikes are one action. That was until I read on here that I target multiple creatures in range with the two unarmed strikes. So with that being said;

How many times should I be rolling for attack when using Flurry of blows alongside a normal attack with a monk weapon?

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You should have made a total of 3 attack rolls - 1 for the staff, and 1 for each unarmed strike in the Flurry of Blows.

Every time you make an attack, you should make an attack roll. This is, actually, the definition of an attack:

If there’s ever any question whether something you’re doing counts as an attack, the rule is simple: if you’re making an attack roll, you’re making an attack.

It doesn't matter whether your action involves making 1 attack or 20 attacks - you still make an attack roll for each attack.

However, you might question whether Flurry of Blows counts as an attack, since it doesn't actually say it grants you an attack, it says it grants you "unarmed strikes".

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.

So what's an unarmed strike? Unarmed strikes are defined on page 73 of the Basic Rules as:

Instead of using a weapon to make a melee weapon attack, you can use an unarmed strike : a punch, kick, head-butt, or similar forceful blow (none of which count as weapons).

An unarmed strike is a melee weapon attack. Therefore, every time you make an unarmed strike, you make an attack roll.

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