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Is the ranged attack resulting from a monk/rogue's Deflect Missiles eligible to add sneak attack damage? For example, if the creature who made the initial ranged attack is engaged in melee as per the rules of Sneak Attack, or if the Monk/Rogue were to somehow have advantage on the roll, for example by way of a spent inspiration point.

I haven't come across anything that seems to openly rule it out, but the idea of throwing somebody's crossbow bolt back at them and doing 1d8 +3d6 damage (at Monk 14/ Rogue 6) seems a little broken to me.

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Not necessarily

The rules for sneak attack state that:

The attack must use a finesse or a ranged weapon. (PHB 96)

Most thrown weapons are actually melee weapons with the thrown property, and using something for a ranged attack does not make it into a ranged weapon (official confirmation by JC). So you will be able to sneak attack with a caught dagger (as it has the finesse property) or a dart (as it is a ranged weapon), but not with a handaxe.

As for caught missiles, they are not technically weapons, they are ammunition. This means they count as an improvised weapon. Thus they will not have any properties (ie. finesse). Whether an arrow or bolt counts as an improvised ranged weapon is up to the DM.

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    \$\begingroup\$ A weapon with the thrown property is a ranged weapon for the purposes of the ranged attack. “A weapon that can be used to make a ranged attack has a range shown in parenthesises after the ammunition or thrown property” (PHB under the “Range” property) \$\endgroup\$ – illustro Jul 7 '18 at 18:12
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    \$\begingroup\$ @illustro "The act of throwing a melee weapon doesn't transform it into a ranged weapon." Jeremy Crawford here \$\endgroup\$ – Szega Jul 7 '18 at 18:22
  • \$\begingroup\$ If a melee weapon doesn’t have the thrown property it is an improvised weapon. If it has the thrown property it’s a ranged weapon when it’s thrown. \$\endgroup\$ – illustro Jul 7 '18 at 18:23
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    \$\begingroup\$ @illustro: Mind citing a source on that? Thrown weapons don't become ranged weapons when thrown; they remain melee weapons, just ones that can be used to make a ranged attack. The thrown property allows you to make a ranged attack with it (using the same ability score modifier - usually Strength, unless it's a finesse weapon - that you would use for a melee attack with it), but it doesn't change the weapon's type. \$\endgroup\$ – V2Blast Jul 7 '18 at 18:38
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    \$\begingroup\$ The fact that ranged weapons are used to attack a target at a distance doesn't mean that other weapons can't be. Weapons with the thrown property can be used to make ranged weapon attacks; nothing suggests that they "become" ranged weapons for the duration of an attack. (Nothing suggests that any weapons change their type during specific attacks at all, besides some weapons being treated as improvised weapons when used in a way they're not designed for.) In any case, perhaps we should take this discussion to Role-playing Games Chat. \$\endgroup\$ – V2Blast Jul 7 '18 at 18:54

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