Old-Fashioned Pineapple Upside Down Cake

A slice of pineapple upside down cake with a bite on a fork to show texture.

5 from 1 vote

Old-Fashioned Pineapple Upside Down Cake

This old-fashioned pineapple upside-down cake is made completely from scratch with buttery brown sugar topping, juicy pineapple rings, and tender vanilla cake. A classic vintage dessert that is simple, reliable, and perfect for Sunday dinners, holidays, or anytime you want a nostalgic homemade treat.

Prep Time15

Cook Time40

Cooling Time20

Total Time1 15

Course: Dessert

Cuisine: American

Keyword: from-scratch pineapple upside down cake, Old-Fashioned Pineapple Upside-Down Cake, pineapple upside down cake recipe

Servings: servings

Calories: 383kcal

Author: Melissa Norris

Cost: Varies

Equipment

Mixing Bowls
mixer
cake pan 9" round or 8" square

Ingredients

Topping

1/4 cup unsalted butter melted
1/2 cup brown sugar packed
8 slices pineapple fresh or canned
20 whole cherries Luxardo or maraschino
1/4 teaspoon cinnamon
1/4 teaspoon ginger ground

Cake

1/2 cup cake flour
1 teaspoon baking powder
3/4 cup sugar
1/2 teaspoon salt I love Redmond Real Salt. Use code “Pioneering” for 15% off.
1/2 cup butter room-temperature
2 large eggs
2 teaspoons vanilla I love this homemade vanilla extract recipe.
1/2 cup milk
1/4 cup pineapple juice If using canned pineapple, reserve the liquid.

Instructions

Preheat the oven to 350°F. Bake in a 9" x 2" round cake pan or an 8" square cake pan.
Mix the melted butter, brown sugar, cinnamon and ginger together in a small bowl. Put the topping mixture into the bottom of the cake pan.
Blot the pineapple slices to remove excess liquid then layer on top of the liquid mixture, place a cherry in the center of each pineapple ring. Place the pan in the refrigerator to allow the topping to solidify a bit while you prepare the cake batter.
Cream the butter on high, about 1 minute. Add the eggs, vanilla and milk and beat until combined. Add the dry cake mix to the wet ingredients and mix on low. While it is mixing slowly add the pineapple juice.
Continue beating until all of the ingredients are just combined. Don't over mix because that will result in a tougher cake. The batter will be on the thicker side.
Take the topping out of the fridge and spread the cake batter over top evenly.
Bake for 40-50 minutes. To prevent the top from over browning before the cake is fully baked, tent the top with foil. To test for doneness, insert a toothpick in the center of the cake. If it comes out clean, the cake is done.
When done, remove from the oven and place on a wire rack. Allow to cool for 20 minutes. After the cooling time (it'll still be warm), invert the cake onto a platter or cake stand. Allow the juices from the topping to run over the sides.
Allow the cake to cool at room temperature before slicing and serving. You can slice and serve while it's warm but the slices will be messy.

Notes

Recipe Tips:

Blotting the pineapple prevents excess liquid from thinning the topping.
Do not overmix the batter or the cake will be dense instead of tender.
Invert the cake while warm so the topping releases cleanly.
Use a rimmed platter to catch the caramelized juices.

Storage Instructions:

Cover and store leftovers in the refrigerator for up to 3 days. For longer storage, slice the cake and freeze for up to 3 months. Do not freeze the cake whole, as the topping does not thaw evenly. Thaw slices at room temperature before serving.

Nutrition