Prepare at 13 x 9 x 2 inch baking dish with baking spray.
Prepare the cake mix as directed on the box.
Pour into the prepared baking dish and bake for approximately 32 minutes, or until a toothpick inserted comes out clean.
Meanwhile, pour the pineapple along with its juice into a saucepan along with the 1 cup of sugar. Bring this mixture to a boil over medium heat while stirring constantly. Remove from heat and allow it to slightly cool.
When the cake is done, remove it from the oven and pierce holes into the cake using the prongs of a fork. Pour the pineapple mixture over the hot cake and set it aside.
Prepare the instant pudding according to the package directions. Spread the pudding over the cake/pineapple and refrigerate until it is thoroughly chilled.
Whip the heavy whipping cream with the 1/2 cup sugar until it is stiff. Cover the top of the cake with the whipped cream.