In a medium mixing bowl, whisk together the instant vanilla pudding mix and milk until the mixture is smooth and begins to thicken. Let it sit for about 5 minutes to fully thicken.

Gently fold the Cool Whip into the pudding mixture until it is fully combined and fluffy.

Stir in the powdered sugar and vanilla extract until evenly mixed.

Layer half of the sliced fresh strawberries evenly across the bottom of the graham cracker crust.

Spoon half of the Cool Whip and pudding mixture over the strawberries, spreading it evenly.

Add the remaining strawberries as the next layer.

Spread the remaining Cool Whip mixture over the top layer of strawberries, smoothing it out to the edges.

Chill the pie in the refrigerator for at least 2 hours before serving to allow it to set properly.