Prepare the cake according to the package instructions in a greased 9x13-inch baking pan.
While the cake is baking, combine the crushed pineapple and sugar in a saucepan over medium heat until sugar dissolves.
When the cake is done, allow it to cool for 10 minutes. Poke holes in the top with a fork.
Pour the warm pineapple mixture over the cake, ensuring it seeps into the holes.
Let the cake cool completely. Meanwhile, prepare the cream cheese frosting by beating the cream cheese and butter together until smooth, then gradually add the powdered sugar and milk until creamy.
Once the cake is cool, frost it with the cream cheese mixture and top with chopped pecans if desired.
Chill the cake in the refrigerator for at least 2 hours before serving for the best flavor.
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Notes
Store leftovers in the refrigerator for up to a week.