My parents came to visit me in Omaha this weekend and I wanted to make something super special for their visit and for my dad’s birthday. My dad’s favorite cake is my Aunt Sue’s Classic Pineapple Upside-Down Cake (slightly borrowed from a Duncan Hines recipe). It is so easy to make, the hardest part is not eating all the sugar coated pineapple slices before the cake is finished.

My original plan was to make this cake a little boozy, but with little hands helping me in the kitchen I thought the PG version would be just as amazing. Never fear, I wrote down the booze substitutions for your drinking enjoyment. So go ahead and have a slice or two of this delicious, caramelized, pineapple cake.


1 pkg Duncan Hines® Moist Deluxe® Pineapple Supreme Cake Mix

3 eggs

2  20 oz cans pineapple rings

1 1/3 cups pineapple juice (from the 2  20 oz cans)*

1/3 cup vegetable oil

1 stick butter

2-3 tbsps rum (optional)

1 cup packed brown sugar

Maraschino cherries

*For the boozy version use 1 cup pineapple juice and 1/3 cup spiced rum


1) Preheat the oven to 350 degrees

2) In a medium bowl mix together the Duncan Hines® cake mix, eggs, pineapple juice and vegetable oil until smooth then set aside.

3) Melt butter in a a small bowl. (This is where you would add the 2-3 tbsp rum if you wanted to spice it up). Pour melted butter into 13 x 9 glass pan, completely covering the bottom. Sprinkle brown sugar over the buttered area.

4) Place pineapple slices on the butter-brown sugar mixture and place a single maraschino cherry inside each pineapple ring. Do this until the entire bottom is covered with pineapples and cherries.

5) Pour cake batter into the prepared dish, spreading evenly over the pineapple rings. Bake for 40-45 minutes or until the cake is a golden brown and not jiggly in the center. Let cool completely (20-30 minutes)

This might be the trickiest part so be extra careful so you don’t drop the cake. Though I wouldn’t judge if you ate it off the floor. 

6) Run a knife between the cake and the baking dish to make sure they won’t stick. Place cookie sheet face down on top of cool cake, hold the glass dish with your fingers and the cookie sheet with your thumb. When you feel secure flip the sheet and cake towards you and upside-down giving it a slight shake. The cake should easily fall out, revealing the perfectly caramelized pineapple.

Cut off a slice and share with your loved ones.