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Can a Battle Master use trip on a prone enemy? The player just wants the extra damage. Is it possible, or against the rules?

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Prone is a condition, and generally a condition is redundant. Damage is cumulative and generally untied to the condition. You can't knock an unconscious person more unconscious, but you can damage them more. You can't make a poisoned character more poisoned, but you can do more poison damage.

So in the spirit of similarity, I would say that yes, you can do the damage. You just can't make them "more prone". Ignore the saving throw if you wish, but the damage of the maneuver should stand.

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Yes

The text of the Trip Attack (PHB 74) is:

Trip Attack. When you hit a creature with a weapon attack, you can expend one superiority die to attempt to knock the target down. 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 knock the target prone.

There are no preconditions to meet, and it doesn't specify that the maneuver must be used against an enemy who can be knocked prone.

So yes, you can use it against a prone target. You're not going to knock them any more prone, but that doesn't sound like what your player is going for.

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  • \$\begingroup\$ I always rationalized the superiority die extra damage as part of the fall inflicted by the trip. \$\endgroup\$
    – Slagmoth
    Sep 30, 2016 at 18:06
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    \$\begingroup\$ Good flavor, but the damage gets inflicted regardless if the trip attempt is successful. \$\endgroup\$
    – UrhoKarila
    Sep 30, 2016 at 18:15
  • \$\begingroup\$ I rationalized the extra damage as hooking/kicking the opponent's leg as part of trying to knock them down. Even if they don't fall, a kick to the shin still hurts. :) \$\endgroup\$ Sep 30, 2016 at 19:09

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