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Quoting both of the spells, Sleep (PHB p.276) states:

(...) each creature affected by this spell falls unconscious until the spell ends, the sleeper takes damage, or someone uses an action to shake or slap the sleeper awake.

And Entangle (PHB p.238):

Grasping weeds and vines sprout from the ground in a 20-foot square starting from a point within range. For the duration, these plants turn the ground in the area into difficult terrain.

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

When the spell ends, the conjured plants wilt away.

So by the spell description, Entangle doesn't cause any damage to the affected creatures, which makes me think it wouldn't wake creatures affected by Sleep spell.

Moreover, unconscious creatures automatically fail their Strength Saving Throws (PHB 292), so they get automatically entangled as well.

Do these entangling vines affect the asleep creatures in any way so they wake up?

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2 Answers 2

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RAW, they will not awaken.

The sleep spell clearly lists the ways to awaken the sleeper. This is magical slumber, which can occur even in the pitch of mortal combat (in fact usually in the pitch of mortal combat). It is not ordinary sleep. Note that the action to awaken the sleeper is to take damage, or be shaken or slapped. The spell says nothing about loud noises, bright lights or other things that normally awaken sleepers.

The entangle spell has no language in it that describes a level of violence even so mild as a slap or shake. A DM is free to interpret this otherwise (that's their job), but there is no specific language in the rules to suggest that the entangle spell will awaken a magically slept person.

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    \$\begingroup\$ Web wouldn't awaken them, but the vines in entangle actually have to grasp them to restrain them, which to me is equivalent to a shake. Regardless, might want to edit the end of your answer, since I think you meant to re-type entangle there. \$\endgroup\$
    – Seth R. Feldman
    Commented Mar 17, 2018 at 15:41
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    \$\begingroup\$ Thanks for the catch, Seth. My answer is based on the functional similarity of entangle to web, and the fact that neither has specific wording that requires a violent interpretation. The action of the vines could be a violent, jerking grab, or simply a silky gliding of vines around limbs until they are restrained. With nothing to definitively choose the former interpretation, we are left with the language of the spell, which has no specifically violent wording. As your answer says, a DM can interpret differently. I just felt my approach required less DM injection into the situation. \$\endgroup\$
    – keithcurtis
    Commented Mar 17, 2018 at 15:56
  • \$\begingroup\$ A closer re-read of entangle does not even specifically say that target is grasped. Merely that being within the area can cause them to be restrained. There could easily be just a mass of vines that make it impossible to effectively move. \$\endgroup\$
    – keithcurtis
    Commented Mar 17, 2018 at 15:59
  • \$\begingroup\$ The vines are 'grasping' and that is why the area is difficult terrain - they pull at the creatures in the area. No, a grasp is not literally a shake - but it is also unrealistic to expect the sleep spell to specify every single word for a physical touch that is forceful but not strong enough to do damage. \$\endgroup\$
    – Kirt
    Commented Feb 27 at 15:47
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This is entirely a DM decision. They have to determine if the vines and weeds grasping the player count as a shake or slap, as the other conditions to interrupt the Sleep spell are not met. The entangle spell takes an action to cast, so it makes the requirement of taking an action. In my game, it would also wake them up, but probably AFTER they auto-failed the save. But this is a game-by-game, DM decision, and not one that can be answered RAW.

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