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Fey Wanderers get an ability called Beguiling Twist which reads:

(...) whenever you or a creature you can see within 120 feet of you succeeds on a saving throw against being charmed or frightened, you can use your reaction to force a different creature you can see within 120 feet of you to make a Wisdom saving throw against your spell save DC. If the save fails, the target is charmed or frightened by you (your choice) for 1 minute. The target can repeat the saving throw at the end of each of its turns, ending the effect on itself on a successful save.

Let's say that someone used a fear effect in round 1 and the target succeeded on the save. The Fey Wanderer used Beguiling Twist against Enemy B and Enemy B failed the saving throw. In subsequent rounds, when Enemy B eventually succeeds on the saving throw they get at the end of their turns, could the Fey Wanderer trigger Beguiling Twist again granted that their reaction is available?

I see no reason why it shouldn't work this way, but I've never heard it talked about and I've seen some guides talk about Beguiling Twist as if it doesn't trigger itself.

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The text is ambiguous, up to the DM

Here the relevant text is the following :

whenever you or a creature you can see within 120 feet of you succeeds on a saving throw against being charmed or frightened

The core of the issue here is the word "being". A "saving throw against being charmed or frightened" can be read in a few different ways :

  • Saving throws that decide whether or not you become charmed or frightened
  • Saving throws that decide whether or not you stay charmed or frightened
  • Saving throws that decide whether or not you'll be charmed or frightened after its resolution (in other words, both of the above)

Depending on which reading you believe is the most correct one, this ability is drastically altered.

  • With the first reading, you can only trigger this effect when an effect would inflict charmed or frightened to a creature. As such, a creature recovering from one of those effects through a saving throw would not allow you to trigger the effect.
  • With the second reading, you can only trigger this effect when a creature that's already afflicted with charmed or frightened recovers from the condition through a saving throw. A creature succeeding a saving throw to prevent the affliction from happening in the first place would not allow you to trigger the effect.
  • With the third reading, you can trigger this effect any time a saving throw would either end the condition or prevent it altogether.

I could not find any proof as to whether either of those interpretation is more or less "correct" in English language, so if you're the DM you'll have to pick the one you believe makes the most sense, or is the most balanced for your campaign. If you're the player, I recommend asking your DM, at the very least to avoid a last-minute bad surprise.

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    \$\begingroup\$ The feature does say that a creature can "repeat the saving throw at the end of each of their turns". Notably: repeat. It's not a new saving throw to end the effect, it's the same one. \$\endgroup\$ Commented Apr 26 at 15:38
  • \$\begingroup\$ Although I personally would interpret "against being charmed" as your first case (i.e., only the initial, not to break), sadly (for me, good for you) the consensus seems pretty clear that it's your third one. For example, on Fey Ancestry, or other similar abilities, like Plasmoid natural resilience "advantage against being poisoned". \$\endgroup\$
    – justhalf
    Commented Apr 26 at 21:36
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    \$\begingroup\$ @JoakimM.H. But we could also read the snap-out-of-it text where "... ending the effect ... on a successful save" means what it says -- it's a saving throw to end the effect, and not a save to resist the effect. Then "repeat the save" is merely a plain English shortcut to say it's also Wisdom vs. DC. \$\endgroup\$ Commented Apr 26 at 22:53
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Yes

The effect of Beguiling Twist is a saving throw against being charmed (assuming the ranger chooses charming):

...to force a different creature you can see within 120 feet of you to make a Wisdom saving throw against your spell save DC. If the save fails, the target is charmed or frightened by you (your choice) for 1 minute. The target can repeat the saving throw at the end of each of its turns, ending the effect on itself on a successful save.

A creature succeeding on the intial savibg throw would definitely satisfy the condition for Beguiling Twist's reaction:

... whenever you or a creature you can see within 120 feet of you succeeds on a saving throw against being charmed or frightened ...

The contentious matter is whether only the intial saving throw counts as being "against being charmed" or the subsequent one as well.

We can compare this to the Halfing's Brave trait against the Adult Red Dragon's Frightful Prescence, which use the same wording:

Brave. You have advantage on saving throws against being frightened.

**Frightful Prescence. Each creature ... must succeed on a DC 19 Wisdom saving throw or become frightened for 1 minute. A creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success.

I have not heard of anyone ruling that Brave only grants advantage on the initial saving throw and not any others, as that would be very unintuitive. However, that would be the equivalent ruling required to say that Beguiling Twist cannot trigger on its own saving throws.

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