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A slice of homemade Pineapple Upside Down Cake Recipe with a caramelized pineapple ring and cherry on top, served on a white plate with extra maraschino cherries on the side.

Pineapple Upside Down Cake Recipe

A classic, crowd-pleasing dessert perfected over decades—this Pineapple Upside Down Cake Recipe features caramelized pineapple rings, a rich brown sugar glaze, and an incredibly moist vanilla cake that tastes even better the next day.
5 from 1 vote
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Course: Dessert
Cuisine: American
Keyword: Dole old fashioned pineapple upside down cake, Old fashioned pineapple upside down cake, Pineapple Upside Down Cake Recipe, Pineapple upside down cake with box mix, pineapple upside-down cake recipe best ever, Upside down pineapple
Prep Time: 20 minutes
Cook Time: 45 minutes
Cooling Time: 5 minutes
Total Time: 1 hour 10 minutes
Servings: 8
Calories: 320kcal
Cost: $11

Equipment

  • 9-inch cast iron skillet (Or 9-inch round cake pan)
  • Mixing bowl (Large size)
  • Electric mixer (Handheld or stand mixer)
  • Measuring cups & spoons (For accurate measurements)
  • Can opener (For opening canned pineapple)

Ingredients

Topping

  • 1 can Pineapple slices - Drain and pat dry
  • ⅓ cup Light brown sugar - Packed
  • ¼ cup Unsalted butter - Melted in skillet
  • 8 Maraschino cherries - One for each pineapple ring

Cake

  • 1 ½ cups All-purpose flour - Spoon & level for accuracy
  • ¾ cup Granulated sugar
  • 2 Large eggs - Room temperature
  • ½ cup Whole milk - Or substitute (see swaps)
  • ⅓ cup Vegetable oil - Or melted butter
  • 1 teaspoon Pure vanilla extract
  • 2 teaspoon Baking powder
  • ¼ teaspoon Salt
  • 2 tablespoon Pineapple juice - Optional, from canned pineapple

Instructions

  • Preheat oven to 350°F. Drain the pineapple slices and pat them dry with paper towels.
  • Melt butter in a skillet, sprinkle brown sugar evenly, and arrange pineapple and cherries on top.
    Freshly baked pineapple upside-down cake in a cast iron skillet with caramelized topping, pineapple rings, and cherries, on a marble countertop.
  • In one bowl, mix dry ingredients. In another, beat eggs and sugar, then add milk, oil, and vanilla.
    Thick, creamy pineapple upside-down cake batter in a mixing bowl with a wooden spoon, surrounded by baking ingredients on a sunlit counter.
  • Gently fold dry ingredients into the wet mixture. Do not overmix.
  • Pour the batter over the fruit topping and bake for 40–45 minutes until fully cooked.
  • Let the cake cool for 5 minutes. Run a knife around the edge, flip onto a plate, and lift the skillet.

Notes

Nutrition information is automatically calculated and should be considered an approximation. Actual values may vary based on specific ingredients used and portion sizes
 

Nutrition

Serving: 110g | Calories: 320kcal | Carbohydrates: 45g | Protein: 3g | Fat: 14g | Saturated Fat: 6g | Polyunsaturated Fat: 2g | Monounsaturated Fat: 5g | Cholesterol: 55mg | Sodium: 180mg | Potassium: 150mg | Fiber: 1g | Sugar: 28g | Vitamin A: 350IU | Vitamin C: 4mg | Calcium: 60mg | Iron: 1.3mg