Cinnamon Pecan Pineapple Upside-Down Cake
This retro-inspired classic features a simple vanilla cake topped with caramelized brown sugar, cinnamon, pineapples, maraschino cherries, and pecans.
Servings 10 servings
Ingredients
TOPPING INGREDIENTS
- 4 tbsp unsalted butter
- 1/2 tsp vanilla extract
- 1/2 cup dark brown sugar, firmly packed
- 1 tsp ground cinnamon
- 1 20-oz can of pineapple rings, with juice reserved
- 12-16 maraschino cherries, drained (or more to taste)
- handful of pecan halves (or more to taste)
CAKE INGREDIENTS
- 4 tbsp unsalted butter, at room temperature
- 1/2 cup light brown sugar, firmly packed
- 1/4 cup granulated sugar
- 1 egg, at room temperature
- 1 tsp vanilla extract
- 2 tbsp reserved pineapple juice from the 20-oz can
- 1 1/2 cups all-purpose flour
- 1 3/4 tsp baking powder
- 3/4 tsp salt
- 1/2 cup milk, at room temperature
Instructions
PREP INSTRUCTIONS
- Preheat your oven to 350F.
- Open the can of pineapple rings and remove 2 tbsp of the pineapple juice. Set aside the reserved juice, and you can discard the rest.
- Melt 4 tbsp of butter, then stir in 1/2 tsp vanilla extract. Set aside.
- Stir together the dark brown sugar and 1 tsp ground cinnamon until combined.
- Have a cake plate or cake stand ready for later.
TOPPING INSTRUCTIONS
- Pour the melted butter directly into a 9" round baking pan. DO NOT SPRAY OR LINE THE BOTTOM OF THE PAN.
- Sprinkle the cinnamon sugar mixture all over the melted butter.
- Arrange the pineapple rings in a single layer over the sugar and butter. You can squish the rings together to fit more in the pan; just be sure the rings don't overlap.
- Arrange the maraschino cherries inside and around the rings, then add the pecans around the cherries and pineapple. Again, everything must be in a single layer. Then, set cake pan aside.
BAKING INSTRUCTIONS
- Use a hand-mixer to cream together the 4 tbsp softened butter, granulated sugar, and light brown sugar in a large bowl until light and fluffy.
- Beat in the egg, the 1 tsp vanilla extract, and the reserved pineapple juice until combined.
- In a separate medium bowl, whisk together the flour, baking powder, and salt.
- Alternate adding the dry ingredients and the milk into the butter mixture, beating on low between each addition until ingredients are just combined.
- Carefully pour the cake batter over the arranged pineapple, cherries, and nuts in the cake pan. Smooth batter to the edges of the pan to ensure an even cake layer.
- Bake the Cinnamon Pineapple Upside-Down Cake at 350F for about 40 minutes, or until a toothpick inserted into the middle of the cake comes out clean.
- Remove Cinnamon Pineapple-Upside Down Cake from the oven and let cool in pan on a wire track for ONLY 5 MINUTES.
- Run a knife around the edges of the pan to loosen the sides of the cake.
- Using oven mitts, cover the cake with the bottom of your cake plate/stand. Securely hold the cake plate against the baking pan, then quickly but carefully flip the cake over so that the pineapple "bottom" is now the topping of the cake. Carefully lift the cake pan up and away from the cake. Let Cinnamon Pineapple Upside-Down Cake cool completely before serving.