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Preheat the oven to 350 degrees. Spray a 13- by 9-inch baking pan with cooking spray and set aside.
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Combine the cake mix, pudding, eggs, milk, and oil in a large mixing bowl. Beat with an electric mixer until smooth, scraping the sides and bottom of the bowl as necessary.
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Pour into the prepared pan, smooth the top, and bake 32 to 42 minutes, until a toothpick inserted into the center of the cake comes out clean.
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While the cake is in the oven, combine the pineapple WITH JUICES and sugar in a small saucepan set over medium heat. Bring to a boil, stirring often. Boil for 3 minutes, still stirring.
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Set aside while the cake finishes baking.
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Set the baked cake on a wire rack to cool for 5 minutes. Use a long-tined fork to poke holes all over the cake, going about 3/4 of the way down into the cake. (If you don’t have a long-tined fork you can use a toothpick and swirl it around to make the holes a little bigger.)
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Pour the pineapple over the top of the still-hot cake and use a rubber spatula to spread it around evenly (do this gently).
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Cool completely before making the frosting.