Preheat oven to 350°F. Spray a 9x13-inch baking dish with nonstick cooking spray.
In a mixing bowl (or the bowl of a stand mixer) add in 15.25 ounce box yellow cake mix, 1 teaspoon ground cinnamon, 1 cup mashed ripe banana, 8 ounce can crushed pineapple, undrained, 3 large eggs, 1/4 cup vegetable oil and ¼ cup milk. Mix until combined.
Pour batter into prepared baking dish and bake on the middle oven rack for about 28–32 minutes or until set. NOTE: Oven times can vary so go by doneness, not just by time. An inserted toothpick should come out clean when ready.
Poke holes all over warm cake using a wooden spoon handle. If you don’t have a wooden spoon, use something of a similar size, you want holes large enough for the pudding to go into.
Let cake cool while you prepare the filling.
In a bowl, add 14 ounce can sweetened condensed milk, 3.4 ounce box INSTANT vanilla pudding and ½ cup milk. Mix together with an electric hand mixer until thickened.
Pour sweetened condensed milk mixture evenly over the cake (aim for the holes as much as possible.)
In a separate bowl, beat 8 ounce block cream cheese, softened to room temperature, ½ cup powdered sugar and 1 teaspoon vanilla extract with an electric hand mixer until smooth.
Gently stir in 1 ½ cups whipped topping (Cool Whip).
Spread frosting over cooled cake. Evenly sprinkle the top with 1 cup chopped pecans.
Then slice and enjoy! Note: I think this cake is best after it has chilled (covered) in the refrigerator for at least a few hours.
Notes
Please refer to my FAQ’s (Frequently Asked Questions) and ingredient list above for other substitutions or for the answers to the most common questions.
This makes between 12-15 servings depending on how you cut the cake.