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:
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:
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:
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.