Pineapple Rum Upside-Down Cake

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A timeless American classic gets a boozy Caribbean makeover! This Pineapple Rum Upside-Down Cake features golden pineapple slices caramelized in brown sugar, nestled atop a fluffy, buttery vanilla-rum cake. A splash of dark rum gives it depth and warmth, while maraschino cherries and a glossy finish make it celebration-ready.

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Yields12 Servings
Prep Time25 minsCook Time45 minsTotal Time1 hr 10 mins
10–12 servings (9-inch round cake)
Topping
 ¼ cup unsalted butter, melted
 ½ cup light brown sugar, packed
 9 pineapple rings (canned or fresh)
 Maraschino cherries (optional, for center of rings)
Cake Batter
 1 ½ cups all-purpose flour
 1 ½ tsp baking powder
 ¼ tsp salt
 ½ cup unsalted butter, softened
 ¾ cup granulated sugar
 2 large eggs
 ¼ cup dark rum (or substitute with pineapple juice for non-alcoholic version)
 ¼ cup pineapple juice (from the can or fresh)
 1 tsp vanilla extract
 ½ cup sour cream (adds tenderness)
Prepare the Topping
1
  1. Preheat your oven to 350°F (175°C).

  2. Pour melted butter into a greased 9-inch round cake pan.

  3. Sprinkle brown sugar evenly over the butter.

  4. Arrange pineapple rings on top of the sugar, gently pressing them in.

  5. Place a cherry in the center of each ring (optional but classic).

Make the Cake Batter
2
  1. In a medium bowl, whisk together flour, baking powder, and salt.

  2. In a large bowl, cream butter and sugar together until pale and fluffy (2–3 minutes).

  3. Beat in eggs, one at a time, followed by vanilla, rum, and pineapple juice.

  4. Mix in sour cream until just combined.

  5. Gradually add the dry ingredients, mixing until just smooth. Do not overmix.

Assemble and Bake
3
  1. Carefully spoon the batter over the pineapple topping in the cake pan.

  2. Smooth the top gently with a spatula.

  3. Bake for 40–45 minutes, or until a toothpick inserted in the center comes out clean and the top is golden.

  4. Let cool in the pan for 10–15 minutes only (too long and it may stick!).

Invert and Serve
4
  1. Run a knife around the edges to loosen the cake.

  2. Invert onto a serving plate in one swift motion.

  3. Let it cool fully before slicing.

Serving Ideas
5
  • Serve with a dollop of whipped cream or vanilla ice cream.

  • Drizzle with extra dark rum for a grown-up flair.

Tips & Variations
6
  • Use fresh pineapple slices for a less-sweet version with extra tang.

  • For more rum flavor, brush the warm cake with a rum syrup (equal parts rum and sugar heated until dissolved).

  • Want a richer cake? Replace 2 tablespoons of pineapple juice with more rum.

Ingredients

10–12 servings (9-inch round cake)
Topping
 ¼ cup unsalted butter, melted
 ½ cup light brown sugar, packed
 9 pineapple rings (canned or fresh)
 Maraschino cherries (optional, for center of rings)
Cake Batter
 1 ½ cups all-purpose flour
 1 ½ tsp baking powder
 ¼ tsp salt
 ½ cup unsalted butter, softened
 ¾ cup granulated sugar
 2 large eggs
 ¼ cup dark rum (or substitute with pineapple juice for non-alcoholic version)
 ¼ cup pineapple juice (from the can or fresh)
 1 tsp vanilla extract
 ½ cup sour cream (adds tenderness)

Directions

Prepare the Topping
1
  1. Preheat your oven to 350°F (175°C).

  2. Pour melted butter into a greased 9-inch round cake pan.

  3. Sprinkle brown sugar evenly over the butter.

  4. Arrange pineapple rings on top of the sugar, gently pressing them in.

  5. Place a cherry in the center of each ring (optional but classic).

Make the Cake Batter
2
  1. In a medium bowl, whisk together flour, baking powder, and salt.

  2. In a large bowl, cream butter and sugar together until pale and fluffy (2–3 minutes).

  3. Beat in eggs, one at a time, followed by vanilla, rum, and pineapple juice.

  4. Mix in sour cream until just combined.

  5. Gradually add the dry ingredients, mixing until just smooth. Do not overmix.

Assemble and Bake
3
  1. Carefully spoon the batter over the pineapple topping in the cake pan.

  2. Smooth the top gently with a spatula.

  3. Bake for 40–45 minutes, or until a toothpick inserted in the center comes out clean and the top is golden.

  4. Let cool in the pan for 10–15 minutes only (too long and it may stick!).

Invert and Serve
4
  1. Run a knife around the edges to loosen the cake.

  2. Invert onto a serving plate in one swift motion.

  3. Let it cool fully before slicing.

Serving Ideas
5
  • Serve with a dollop of whipped cream or vanilla ice cream.

  • Drizzle with extra dark rum for a grown-up flair.

Tips & Variations
6
  • Use fresh pineapple slices for a less-sweet version with extra tang.

  • For more rum flavor, brush the warm cake with a rum syrup (equal parts rum and sugar heated until dissolved).

  • Want a richer cake? Replace 2 tablespoons of pineapple juice with more rum.

Notes

Pineapple Rum Upside-Down Cake
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