Combine 1 cup strawberries and sugar in a blender; process until smooth. Thinly slice remaining 1 cup strawberries. Combine strawberry puree and sliced berries in a bowl.
Spoon about 1 tablespoon strawberry mixture into each of 4 stemmed glasses. Top each with 1/4 cup tapioca pudding and 1 1/2 tablespoons strawberry mixture. Repeat layers, ending with strawberry mixture.