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My players were rewaded with two Awakened Trees and an Awakened Shrub for a quest. They are about to encounter a Medusa and I anticipate them sending in one if the awakened plants to scout out the area.

If the awakened plant encounters the medusa first, would it be vulnerable to her gaze attack and possibly turn to stone? The Awaken spell says the "gain senses similar to a human's", though they don't have eyes as far as I know.

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Awakened plants may or may not have eyes, but a medusa's Petrifying Gaze only requires that

a creature that can see the medusa's eyes starts its turn within 30 feet of the medusa

As you say, the Awaken spell grants its target

senses similar to a human's.

This would certainly suggest that it would be able to see. From the Monster Manual (page 8), we have this:

A monster with blindsight can perceive its surroundings without relying on sight, within a specific radius.

Creatures without eyes, such as grimlocks and gray oozes, typically have this special sense, as do creatures with echolocation or heightened senses, such as bats and true dragons.

If a monster is naturally blind, it has a parenthetical note to this effect, indicating that the radius of its blindsight defines the maximum range of its perception.

Most plant-based creatures (for example, blights, or everything in the Fungi section) follow this exact pattern, having blindsight X ft. (blind beyond this radius). The Awakened Tree and the Awakened Shrub have no blindsight, so either they are actually incapable of perceiving their surroundings at all, or they are simply using ordinary sight and are therefore valid targets for a medusa's Petrifying Gaze.

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Yes.

You have it right in your quote of, "gain senses similar to a human's" which would include the sense of taste, touch, smell, hearing, and sight. Typically if a creature does not have conventional sight, it will be noted in the description, such as with the grimlock.

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