Pineapple Upside Down Cake

5 from 1 vote

Pineapple Upside Down Cake

Pineapple Upside Down Cake is bursting with fresh flavor! A caramelized layer of pineapple sits on top of a tender, moist vanilla cake. The surprise crumb layer on the bottom adds the perfect hint of crunch! Add fresh whipped cream and cherries for a polished finish.

Prep Time25

Cook Time48

Total Time1 13

Course: Dessert

Cuisine: Dessert

Servings: slices

Author: Stephanie Simmons

Ingredients

Crumb Layer

1/4 cup salted butter, melted 56 grams
1/2 cup + 1 tbsp all-purpose flour 73 grams
1/4 cup light brown sugar, packed 58 grams
2 tsp raw turbinado sugar optional, but gives a nice little crunch!
pinch of salt
pinch of cinnamon

Pineapple Layer

4 tbsp salted butter + additional for greasing pan 56 grams + additional
1 large ripe pineapple See notes below for canned alternative
1/2 cup light brown sugar, packed 110 grams
1 jar maraschino cherries

Cake

1/2 cup salted butter, softened at room temperature 113 grams
1 cup + 2 tbsp granulated sugar 240 grams
2 large eggs, at room temperature
1 tsp vanilla extract
1/2 cup full fat sour cream, at room temperature 120 grams
1 and 1/2 cups + 2 tbsp all-purpose flour, spooned & leveled 211 grams
1 and 1/2 tsp baking powder
1/4 tsp salt
1/2 tsp cinnamon
1/4 cup milk, at room temperature I used 2%, 60 mL

Whipped Cream

2 tbsp powdered sugar
1 and 1/2 tsp vanilla extract
1/2 cup heavy cream

Instructions

Prep: Preheat oven to 350℉. Butter a 9-inch cake pan WELL, then give it a little spray with nonstick spray too. Slice your whole pineapple into rings, then quarter the rings. Or, use canned rings and quarter those.
Make the Crumb Topping: In a small bowl, melt the butter. Stir in remaining crumb ingredients until a crumbly mixture forms. Set aside.
1/4 cup salted butter, melted, 1/2 cup + 1 tbsp all-purpose flour, 1/4 cup light brown sugar, packed, 2 tsp raw turbinado sugar, pinch of salt, pinch of cinnamon
Make the Pineapple Layer: Add the butter to the pan and pop it in the warm oven to melt it (this only takes 1-2 minutes). Once the butter is melted, sprinkle the brown sugar evenly over the top, then layer on the pineapple pieces and fill in any gaps with maraschino cherries.
1 large ripe pineapple, 4 tbsp salted butter + additional for greasing pan, 1/2 cup light brown sugar, packed
Make the Cake Batter: Cream softened butter in a large mixing bowl for 30 seconds. Add the sugar and mix on high for one minute, until creamed together. Mix in the eggs on medium-high speed for 45 seconds or so, beating until well combined and the batter is smooth. Mix in the sour cream and vanilla until just combined & smooth.
Mix in the dry ingredients on low speed. When a few streaks of flour remain, pour in the milk and finish mixing on low speed.
1/2 cup salted butter, softened at room temperature , 1 cup + 2 tbsp granulated sugar, 2 large eggs, at room temperature , 1 tsp vanilla extract , 1/2 cup full fat sour cream, at room temperature , 1 and 1/2 cups + 2 tbsp all-purpose flour, spooned & leveled, 1 and 1/2 tsp baking powder, 1/4 tsp salt, 1/4 cup milk, at room temperature
Bake: Pour batter over the pineapple, spreading it evenly. Sprinkle the crumb mixture evenly over the batter.
Bake for 45-52 minutes. When done, a toothpick inserted into the center of the cake will come out with moist crumbs, but not wet batter. Let the cake cool in the pan for 10 minutes, then run a knife around the edge to loosen and then invert the cake onto your serving plate.
If the cake seems to be sticking, gently but firmly tap on the bottom of the cake pan with the butt of a butter knife while the cake pan is flipped upside down on the cooling rack. If any pieces of fruit got stuck in the pan, just place them back in their spot on the cake.
Let cake cool as much as you like before cutting and serving. You can speed this up by moving it, uncovered, to the fridge for about 20 minutes.
Whipped Cream: Make the whipped cream according to my easy homemade whipped cream recipe! Make this just before serving the cake.
Serve & Store: Serve with whipped cream and cherries on top! Store leftovers in the fridge for 2-3 days.

Notes

Pineapple: Use one can of pineapple rings, drained, instead of a whole, fresh pineapple if you can't find a ripe one. A ripe pineapple will be more yellow than green on the outside, and if you smell the bottom of it, it should smell like ripe pineapple. (I call this, sniffing the pineapple's butt, HAH.)

Nutrition