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If a mount and rider both fail their saving throw and are both restrained via the spell Web, or Entangle, does it take both creatures actions to try to escape, or only the mounts action?

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Technically, only the mount needs to escape from Web. Even more technically, both the mount and the rider need to escape from Entangle.

Firstly, the Restrained condition:

  • A restrained creature’s speed becomes 0, and it can’t benefit from any bonus to its speed.

  • Attack rolls against the creature have advantage, and the creature’s attack rolls have disadvantage.

  • The creature has disadvantage on Dexterity saving throws.

For our purposes, the bit that matters is that speed becomes 0. That's how spells like Web and Entangle keep you still. This means that if your mount breaks free, it can carry you out, since the only thing keeping you in is that your speed is 0. Next, we have Web:

Each creature that starts its turn in the webs or that enters them during its turn must make a Dexterity saving throw. On a failed save, the creature is restrained as long as it remains in the webs or until it breaks free. A creature restrained by the webs can use its action to make a Strength check against your spell save DC. If it succeeds, it is no longer restrained.

So if the mount breaks out, it can carry the rider out of the webs, whereupon the rider no longer "remains in the webs" and is therefore no longer restrained. Now for Entangle:

A creature in the area when you cast the spell must succeed on a Strength saving throw or be restrained by the entangling plants until the spell ends. A creature restrained by the plants can use its action to make a Strength check against your spell save DC. On a success, it frees itself.

So if your mount breaks free, it can carry you out, but you're still restrained until you make a Strength check. As always, it's up to individual DMs if they want to houserule this or play it as written.

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The entangle interpretation is not necessarily stupid. It could represent the rider being wrapped up in entangling vines which are still retraining them even though the mount has uprooted them by its movement. I would play it as written. – Dale M Jan 31 at 4:16
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@DaleM Good point, edited. I was in a bad mood when I wrote that. – Miniman Jan 31 at 4:23
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@DaleM -- I suspect that that'd be a case where the rider would be restrained to the mount -- sort of "along for the ride" if you will, no? – Shalvenay Jan 31 at 6:50
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@Shalvenay That's how it would work out - with a speed of 0 the rider would be unable to dismount or otherwise move from the mount's back. – Miniman Jan 31 at 7:01

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