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–+ servings
Pineapple Cup Cakes from Virginia Reese
These Pineapple Cup Cakes reflect the mid-century American love for fruit-filled desserts that balanced sweetness with brightness. Pineapple, once considered a special-occasion ingredient, was often used in cakes meant for church socials, potlucks, and celebrations. The recipe combines a tender scratch-made cupcake with a cooked pineapple filling that’s spooned into the center, then topped with a classic butter-based frosting. What makes these cupcakes special is the extra step of coring and filling each one, turning a simple cake into something elegant and memorable. The result is a soft, lightly sweet cake with a sunny pineapple center that feels both nostalgic and festive.
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Prep Time 40 minutes
Cook Time 15 minutes
Total Time 55 minutes
Course Dessert
Cuisine American
Servings 32
Calories 285 kcal

Ingredients
  

Cupcakes

  • 2 cups cake flour (sifted )
  • 1 ⅓ cups granulated sugar
  • ½ cup shortening (Crisco)
  • 1 tsp salt
  • 3 tsp baking powder
  • 2 eggs (unbeaten)
  • ⅔ cup milk (plus ⅓ cup added later)
  • 1 tsp vanilla extract

Pineapple Filling

  • 1 can crushed pineapple (small can, with juice)
  • 1 cup granulated sugar
  • 1 tbsp all-purpose flour
  • 1 cup boiling water

Frosting

  • ¼ lb butter (or margarine)
  • 1 lb powdered sugar
  • Lemon juice (or crea, as needed to thin)
  • 1 tsp vanilla extract
  • food coloring (optional)

Instructions
 

Step 1: Mix Dry Ingredients

  • Add cake flour, sugar, shortening, and salt to a large mixing bowl.
  • Blend until combined.

Step 2: Add Baking Powder and Eggs

  • Stir in baking powder.
  • Add eggs and mix at medium speed for 2 minutes.

Step 3: Add Milk and Vanilla

  • Add ⅓ cup milk and vanilla.
  • Mix again for 2 minutes until smooth.

Step 4: Prepare for Baking

  • Line muffin tins with paper liners.
  • Fill each cup slightly less than half full with batter.

Step 5: Bake

  • Bake at 350°F (moderate oven) for 10–15 minutes, until done.
  • Cool completely.

Step 6: Make Pineapple Filling

  • Mix pineapple, sugar, and flour in a saucepan.
  • Add boiling water and cook until thickened.
  • Let cool.

Step 7: Fill Cupcakes

  • Cut a small circle from the center of each cupcake.
  • Fill the hole with pineapple filling.
  • Replace the cut top.

Step 8: Make Frosting

  • Cream butter in a mixer.
  • Add powdered sugar gradually.
  • Thin with lemon juice or cream to spreading consistency.
  • Mix in vanilla and color if desired.

Step 9: Frost Cupcakes

  • Spread frosting over filled cupcakes.
  • Set until frosting firms slightly.

Tips

  • Use butter instead of shortening for richer flavor.
  • Add a pinch of cinnamon to the filling for warmth.
  • Top with toasted coconut for texture.
  • Use cream cheese frosting for a tangy twist.
  • Make mini cupcakes for party trays.
  • Chill before serving for cleaner slices.
  • Add lemon zest to frosting for brightness.
  • Pipe frosting for a bakery-style finish.

Nutrition

Calories: 285kcalCarbohydrates: 45gProtein: 3gFat: 11gSaturated Fat: 5gPolyunsaturated Fat: 2gMonounsaturated Fat: 3gTrans Fat: 0.2gCholesterol: 28mgSodium: 210mgPotassium: 95mgFiber: 1gSugar: 34gVitamin A: 320IUVitamin C: 6mgCalcium: 55mgIron: 1.1mg
Keyword comfort food, filled cupcakes, homemade frosting, pineapple dessert, potluck favorite, retro recipes, vintage baking
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