Prep the Batter: In a large mixing bowl, combine the yellow cake mix, vanilla pudding, eggs, oil, and milk. Beat with an electric mixer for one minute, scrape down the sides of the bowl, and beat again for about two minutes until the batter is nice and smooth.
Bake: Pour the batter into a greased 9x13-inch baking dish. Bake at 350°F for 30-35 minutes, or until the cake is golden brown and a toothpick inserted into the center comes out clean.
Make the Pineapple Glaze: While your cake is baking, add the undrained crushed pineapple and granulated sugar to a medium saucepan. Bring the mixture just to a boil over medium-high heat, stirring constantly until the sugar is completely dissolved. Remove from heat.
Poke and Pour: As soon as the cake is done, remove it from the oven and immediately poke holes all over the top using a fork or the end of a wooden spoon. While the cake is still hot, carefully pour the hot pineapple mixture over the top, spreading it out evenly. Allow the cake to cool completely.
Whip the Frosting: In a large bowl, beat the softened butter and cream cheese together until smooth and creamy. Gradually add in the confectioner’s sugar, scraping down the sides as needed. Stir in the vanilla extract and fold in the chopped pecans (if using).
Frost and Serve: Drop dollops of the cream cheese frosting onto the completely cooled cake. Gently spread the frosting to cover the cake, being careful not to disturb the pineapple layer underneath. Sprinkle extra chopped pecans on top for garnish before serving.