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The Centaur's racial feature "Charge" reads as follows:

If you move at least 20 feet straight toward a target and then hit it with a melee weapon attack on the same turn, roll the weapon’s damage dice twice and add them together. Once you use this ability, you can’t use it again until you finish a short or long rest. (Source of wording D&D Beyond)

From this I understand that the affected attack(s) must occur after the Charge ability is triggered, and must occur during the same turn the Charge is triggered.

But, as the title question indictes, I'm in doubt whether this wording means that the doubling of the weapons damage dice only occurs on a single attack that hits after the Charge, and if so must it then be the first attack that hits or can it be any attack that hits during that turn? Or would it affect every attack that hits after the Charge during that turn?

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It only happens once. The ability triggers when you hit the target, and once you use it, you can't use it again. That means you will only be able to double the damage for one swing.

It doesn't have to be the first one though, as you get to decide whether you want to use an ability or not. So if the first attack hits but you don't feel like using it, you don't have to. Then, if the second attack hits you happen to qualify for the same trigger again, so you get to decide to use it at that point.

You could even use it if the target provokes an opportunity attack on your turn, for example if it uses its reaction to run away from you, since that still meets the trigger (you moved, it's your turn, and you hit the target you moved towards).

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    \$\begingroup\$ Whereas this is technically how it is written it seems counterintuitive that you get the extra momentum on anything other than the first attack. So it is well within a DMs purvue to limit it to that. I certainly would, but table mileage varies. \$\endgroup\$
    – Slagmoth
    Commented May 29, 2018 at 12:42
  • \$\begingroup\$ @Slagmoth that would make the feature (much) less valuable, though. \$\endgroup\$
    – Erik
    Commented May 29, 2018 at 12:52
  • \$\begingroup\$ Makes it a better narration though. "Your momentum carries you through and you land a telling blow with the extra force." as opposed to "Even though you are at a complete stop now your blows do extra damage presumably because you moved." I know, it is a game and players want all the toys without any limitations to any perceived fun. In my experience constraints breed creativity and better game play, but every table is different. Centaurs don't have any place as PCs in my world anyway so I suppose it is moot other than it is still DMs purvue on that interpretation. \$\endgroup\$
    – Slagmoth
    Commented May 29, 2018 at 13:03
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    \$\begingroup\$ @Slagmoth it's just as good narration as "Your first swing misses, but your second swing still hits with considerable force just before you come to a crashing halt." The table is in charge of the narration, not the rules. And things ending in squares don't suddenly stop moving; that also makes for weird narrative. \$\endgroup\$
    – Erik
    Commented May 29, 2018 at 14:05
  • \$\begingroup\$ This is very true. I just have a hard time with something designed to be mobile only being able to charge once in a combat. Mounted PCs can do it all the time (although not with the same advantages). If I ever allowed this I would likely just limit it to the first attack but grant advantage to it to balance it out. \$\endgroup\$
    – Slagmoth
    Commented May 29, 2018 at 14:10
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One attack only

At least, that is my interpretation. It says "a melee weapon attack", emphasis on 'a'. Plus it uses lowercase 'attack', as opposed to specifying the Attack (capital A) action, which is used elsewhere if an effect is meant to affect every attack within the Attack action (*citation needed).

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    \$\begingroup\$ It looks clear that this feature can only be used on a single attack. However, please explain your logic on how the second attack couldn't also be used rather than just the first (such as if it misses). Otherwise, the bold part of your answer is unsupported. \$\endgroup\$
    – Nick Brown
    Commented May 29, 2018 at 13:02
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    \$\begingroup\$ @Slagmoth and Nick Brown: Yep, you're right. I changed my answer. \$\endgroup\$
    – PJRZ
    Commented May 29, 2018 at 13:20
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Only the attack that is done right after moving.

The ability (emphasis mine):

If you move at least 20 feet straight toward a target and THEN hit it with a melee weapon attack on the same turn

Cambridge dictionary on "then":

  1. Then meaning ‘at that time’

  2. Then meaning ‘next’

  3. Then meaning ‘in addition’

So the natural wording of the ability means the attack must be done right after the movement. And as @PJRZ stated, "a" attack means a single one.

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