Pineapple Upside Down Cupcakes

These pineapple upside down cupcakes offer all the nostalgic flavor of the classic cake in a fun, individual-sized treat. Each cupcake features a buttery brown-sugar pineapple topping with a bright cherry center, baked over a tender pineapple cake. They’re perfect for parties, potlucks, or any time you want a dessert that’s simple to serve yet looks beautifully impressive. Moist, fruity, and delightfully sticky, these cupcakes bring a pop of sunshine to any occasion.

Ingredients

• 1/2 cup sweet cream butter, melted
• 1 1/2 cups light brown sugar
• 24 maraschino cherries
• 1 (20-ounce) can crushed pineapple
• 1 (18.25-ounce) package pineapple cake mix
• 3 large eggs
• 1 1/2 cups pineapple juice
• 1/2 cup canola oil
• 1 tablespoon powdered sugar, for garnish

Directions

1. Position oven rack in the center and preheat oven to 350°F. Spray muffin cups with nonstick baking spray.
2. Add 1 teaspoon melted butter to each muffin cup, then top with 1 tablespoon brown sugar.
3. Place one maraschino cherry in the center of each cup.
4. Add a heaping tablespoon of crushed pineapple and press it gently into the sugar-cherry layer.
5. In a mixing bowl, combine cake mix, eggs, pineapple juice, and oil; mix on low 30 seconds, then on medium for 2 minutes.
6. Fill each muffin well just below the top with batter.
7. Bake 20 minutes, or until a toothpick inserted into the center comes out clean.
8. Cool 5 minutes, then flip cupcakes onto a cooling rack so the cherry topping faces up.
9. Dust lightly with powdered sugar if desired.

Prep Time: 15 minutes | Cooking Time: 20 minutes | Total Time: 35 minutes
Kcal: 230 kcal (per serving) | Servings: 24

Tips

• Drain crushed pineapple well to avoid excess moisture in the topping.
• For cleaner release, run a knife around each cupcake before flipping.

FAQ

Can I make these ahead?
Yes—store covered at room temperature for 1 day or refrigerate up to 3 days.

Can I substitute a yellow cake mix?
You can, but add 1/2 cup pineapple tidbits or extra juice for stronger flavor.

Why did my topping stick?
They may need a longer cooling time, or the pan may need a bit more baking spray.

Can these be frozen?
Yes—freeze individually and thaw at room temperature before serving.