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A situation arose yesterday wherein a player with a fighter that had the Great Weapon Fighting fighting style rolled a '1' on his damage. He re-rolled and got a '2'. He re-rolled AGAIN and got a '4'.

That seemed odd to me, so we checked in the book and it said nothing about only re-rolling once. Not wanting to slow the game, I voiced my concern and let it slide (they were in a thug-fight so it did not matter in the grand scheme of things).

Then this morning I wondered it we had an old copy of the book or what we missed. Is there a rule somewhere that states where you can only reroll once?

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The fighter can reroll (at most) once.

The Great Weapon Fighting style says the following (emphasis added by me):

When you roll a 1 or 2 on a damage die for an attack you make with a melee weapon that you are wielding with two hands, you can reroll the die and must use the new roll, even if the new roll is a 1 or a 2. The weapon must have the two-handed or versatile property for you to gain this benefit.

They can reroll any damage dice that rolled a 1 or 2, but each individual die can be rerolled only once.

If a rerolled damage die is a 1 or 2, they have to accept it. The fighter doesn't get to reroll it again.

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    \$\begingroup\$ That's kind of strange. Was this errata'd (as the OP asked about potentially having an old book) or has it always been like that? \$\endgroup\$
    – Ifusaso
    Oct 24 '19 at 18:15
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    \$\begingroup\$ I have a copy of the first printing, and it reads as quoted. \$\endgroup\$ Oct 24 '19 at 18:43
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    \$\begingroup\$ I have the errata'd pdf version of the PHB, and there is no alteration on this. I would also clarify that this is per dice. For example, a Greatsword uses 2d6. If the player rolls a one or a two on both dice, they can re-roll each d6 once. \$\endgroup\$
    – Ben
    Oct 25 '19 at 4:24

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