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The "Damage Rolls" section of the rules (PHB p. 196, also in the online Basic Rules) says this:

If a spell or other effect deals damage to more than one target at the same time, roll the damage once for all of them. For example, when a wizard casts fireball or a cleric casts flame strike, the spell’s damage is rolled once for all creatures caught in the blast.

The Magic Missile spell (PHB p. 257, also in the online Basic Rules) has this effect:

You create three glowing darts of magical force. Each dart hits a creature of your choice that you can see within range. A dart deals 1d4 + 1 force damage to its target. The darts all strike simultaneously, and you can direct them to hit one creature or several.

  1. If I target three different creatures with the darts, the spell says quite clearly says that the darts strike at the same time and the Damage Rolls rule says that in that case (as multiple targets are being dealt damage at the same time) I roll only once for all of them. So my reading of that is that I roll my four-sided die just once, add 1, and apply that much damage to each target. Is that correct? It seems the straightforward reading, but then the next scenarios make me unsure.
  2. If I target just one creature with all three darts, then it seems that the "more than one target" clause of the Damage Rolls would no longer apply. So, does that mean that I effectively roll 3d4+3 (rolling my four-sided die three separate times, one for each dart), since there's no longer anything saying to use the same roll for each dart?
  3. And how about if I target creature A with one dart, and creature B with two darts? Per the Damage Rolls section I should roll once for both of them, but that doesn't make any sense they should be taking different amounts of damage, right?

I'm sure I'm just reading things too literally, but it all seems rather contradictory to me, and now I'm unsure how many dice should be rolled for Magic Missile in any scenario. Is there further direction somewhere I'm missing? (I currently only have the PHB, the Starter Box, and the online Basic Rules, so maybe there's more guidance in the other books? I wouldn't think so, though.)

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Rules designer Jeremy Crawford addressed this question in a September 2016 tweet:

Magic missile. RAW: You roll 1 damage die (see "Damage Rolls," PH, 196). RAI: It doesn't matter; you choose.

Although Jeremy Crawford's tweets are no longer considered official rulings, the rules he refers to do answer the question. Per the "Damage Rolls" section (PHB, p. 196):

If a spell or other effect deals damage to more than one target at the same time, roll the damage once for all of them.

So, though the ruling in the tweet never really made it to the official Sage Advice Compendium, the "RAW" statement in the tweet accurately reflects the rules.

You are correct that you only need to roll once for all darts, regardless of the number of creatures hit, according to the Rules As Written. But tradition and fun (I like rolling dice!) can override this with little to no effect on the damage dealt, according to the Rules As Intended.

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    \$\begingroup\$ +1 for tradition and fun! Besides, damage is less swingy, closer to the average when you roll more dice. \$\endgroup\$
    – Meta4ic
    Nov 11 '17 at 3:00
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    \$\begingroup\$ The difference can become rather large if you have a feature that lets you add a bonus to one damage roll of a spell, such as Empowered Evocation for Evocation Wizards. \$\endgroup\$
    – CTWind
    Nov 11 '17 at 9:59
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    \$\begingroup\$ @CTWind How does Empowered Evocation work with Magic Missile?- It is consistent with this answer. If you rolled for each missile, you'd still add the int bonus to all missiles. \$\endgroup\$
    – daze413
    Nov 11 '17 at 10:47
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    \$\begingroup\$ Arcane Firearm (rpg.stackexchange.com/questions/177033/…) does that too, hilariously \$\endgroup\$
    – vehementi
    Jun 5 at 19:52
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Since each magic missile, or dart, is not an area of effect damage, I'd say each one does its own 1d4+1 damage. Thus, you roll for each dart, and the rule on page 196 wouldn't apply. The only way that rule would apply is if each dart hit multiple targets, but they do not.

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