Preheat oven to 350 degrees F (175 degrees C). Grease two 9-inch round cake pans with cooking spray.
Combine cake mix, water, eggs, and oil in a large bowl; beat with an electric mixer on low speed until moistened, about 30 seconds. Increase speed to medium and beat until smooth, about 2 minutes. Divide batter between prepared pans.
Bake in the preheated oven until a toothpick inserted into the center comes out clean, 24 to 29 minutes. Cool in the pans for 15 minutes. Invert onto a rack and cool completely, about 20 minutes.
Mix milk, chocolate pudding mix, and confectioners' sugar together in a bowl to make frosting; fold in whipped topping.
Spread half of the frosting over 1 cake. Spread 1/2 cup strawberry glaze over the frosting. Place the second cake on top; cover with remaining frosting. Spread remaining strawberry glaze on top. Arrange strawberries over glaze. Drizzle top and sides of cake with chocolate syrup. Chill cake until serving.
