Go Back
+ servings
easy pineapple upside down cake

Easy Pineapple Upside Down Cake

A moist Easy Pineapple Upside Down Cake with caramelized pineapple rings and cherries, perfect for a tropical dessert. Simple to make and irresistibly delicious!
Print Pin
Course: Dessert
Cuisine: American
Prep Time: 20 minutes
Cook Time: 39 minutes
Servings: 20
Author: Jessica Harmon

Ingredients

  • 3 eggs room temperature (tip: place in a bowl of warm water for 5 minutes if in a rush)
  • 1 small jar of maraschino cherries about 12
  • 2 cans of pineapple rings in juice reserve the juice for the batter – 20 oz cans used, with a few rings leftover
  • cup 250g light brown sugar, packed
  • 6 tablespoons 84g melted butter (we used unsalted)
  • ½ cup 108g vegetable oil (canola preferred)
  • 1 box 15.25 oz yellow cake mix, sifted (we used Duncan Hines Perfectly Moist)
  • 1 small box 3.4 oz instant vanilla pudding mix (no need to prepare it)
  • ½ cup 60g all-purpose flour
  • ½ cup 100g light brown sugar
  • 1 cup 242g sour cream
  • 1 cup 240g pineapple juice (from the canned pineapple rings)
  • teaspoons 10g vanilla extract

For the Brown Sugar Glaze and Topping

  • cups 250g light brown sugar, packed
  • 6 tablespoons 84g melted butter (unsalted recommended)
  • 12 pineapple rings or as many as needed to cover the cake
  • 12 maraschino cherries

Instructions

  • Begin by generously greasing a 9x13 sheet cake pan with vegetable shortening and lightly flouring it. Preheat your oven to 350°F.
  • Melt the butter (we used a microwave) and pour it into the greased pan. Evenly sprinkle the 1¼ cups of packed light brown sugar over the melted butter.
  • From your cans of pineapple rings, set aside one cup of juice for the batter. Arrange the pineapple rings on top of the brown sugar layer in the pan. Feel free to slice additional rings and use them to fill any gaps between the whole rings.
  • Next, remove the maraschino cherries from their jar and place one in the center of each pineapple ring for a pop of color and sweetness.

For the Cake Batter

  • In a mixing bowl, sift the cake mix to remove any lumps. Add the instant vanilla pudding mix, sour cream, brown sugar, flour, eggs, pineapple juice, vegetable oil, and vanilla extract.
  • Mix all the ingredients on medium speed for about a minute. Make sure to scrape down the sides of the bowl to fully incorporate everything, then mix for an additional minute to achieve a smooth, lump-free batter.
  • Carefully pour the batter over the brown sugar, pineapple rings, and cherries in the pan, making sure everything is evenly covered.
  • Place the pan in the preheated oven and bake for 40-45 minutes. You'll know the cake is done when it springs back when lightly touched, and a toothpick inserted into the center comes out clean or with a few crumbs attached. If your cake seems to brown too quickly, you can cover it loosely with foil during the last few minutes of baking.
  • Once the cake is finished, allow it to cool in the pan for about 10 minutes. If the cake has a dome in the center, gently press it down with a clean towel or carefully trim it with a serrated knife for an even surface.
  • For the flip, place your cake platter on top of the sheet pan and, using dish towels or oven mitts to protect your hands, flip the cake upside down onto the platter. Let the cake pan sit upside down for a couple of minutes, allowing the brown sugar glaze to fully coat the cake.
  • Serve warm for the best texture and flavor. If you're not serving immediately, refrigerate the cake and take it out a few hours before serving to let it return to room temperature. The cake tastes best at room temperature or slightly warm, as cold temperatures can affect the texture due to the butter in the recipe.