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Jeremy Crawford previously noted that the Magic Missile spell causes a separate concentration roll by a spell caster for each hit. (Of note, this is different than Mike Mearls' answer which viewed a Magic Missile as one source of damage. As we understand it, Crawford's answer takes precedence.)

An Aboleth's charm notes: "Whenever the Charmed target takes damage, the target can repeat the saving throw."

Does this mean that a PC struck by Magic Missile would get to re-roll the savings throw for each hit by a missile?

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  • \$\begingroup\$ related sidenote: the Dominate spells are subject to the same effects ("Each time the target takes damage, it makes a new Wisdom saving throw against the spell. If the saving throw succeeds, the spell ends.") \$\endgroup\$ – PixelMaster May 14 '18 at 20:17
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Yes. The wording is very similar and while there is some room for interpretation (see this answer) this is the most straightforward reading.

Concentration:

Whenever you take damage while you are concentrating on a spell

Aboleth Enslave:

Whenever the Charmed target takes damage

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It depends on whether you think "Whenever one takes damage" means "Whenever one takes damage for each source of damage" or "Whenever one takes damage for each distinct time damage occurs".

There really hasn't been clear guidance given that I can find, and really this ends up coming down to the same question as "Would striking someone at 0 hit points with an entire Magic Missile spell automatically kill them?" and the analysis in my answer there. The only precedent we have is that Concentration checks specifically check for each source of damage (as "If you take damage from multiple sources" is explicitly called out in the Concentration rules), but other rules that look for damage (such as the one you ask about) don't make clear if they also trigger for each source as well (as a Magic Missile has three sources) or whether they just trigger for each time (as a Magic Missile's damage explicitly happens simultaneously).

It's really about whether you look on the concentration rule as being different from the "normal" case (since it calls out sources explicitly and other rules do not) or whether you consider it to be the normal case as how to handle damage triggers is spelled out more specifically there and it should be used as a precedent for places that it's not spelled out.

As with all the rules, reading and interpreting them is up to your DM. If you're the DM, just go with whichever interpretation you think is most correct or will lead to the most fun gameplay, and ensure your players know how your game will work. At the end of that day, while it might be nice if the rules answered clearly all our questions like this one, the rules are just guidelines for having fun with your group, and they're there to serve you and not the other way around.

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I believe it would be one check because the magic missiles would be three simultaneous damage but if multiple targets each would save.

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  • 1
    \$\begingroup\$ Welcome to RPG.SE! Take the tour if you haven't already, and check out the help center for more guidance. Can you support your claim by citing any evidence from the rules? \$\endgroup\$ – V2Blast May 22 at 3:45

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