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Pineapple Upside-Down Cupcakes

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Jessica Walker
Updated Feb 27, 2026
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Everyone loves cupcakes, and no one can resist pineapple upside-down cake. We've found a way to bring these favorites together in Pineapple Upside-Down Cupcakes. By using a Betty Crocker™ Super Moist™ Yellow Cake Mix, you get a head start on creating incredibly delicious and homemade cupcakes without the fuss. Each bite delivers a delightful combination of sweet fruit and tender cake, making it a memorable treat for kids and adults alike. Say goodbye to slicing and serving—these individual desserts are as convenient as they are delicious.

Recipe Ingredients

Get ready to bake some sunshine! These Pineapple Upside-Down Cupcakes are a delightful twist on a classic. Let's dive into the delicious ingredient details.

Butter: This golden goodness is essential for richness and flavor. In the topping, it combines with brown sugar to create that irresistible caramel-like glaze.

Brown Sugar: The secret to that iconic sticky-sweet, caramelized topping!

Maraschino Cherries: These vibrant red gems add a pop of color and a sweet, slightly almond-like flavor to each cupcake.

Canned Pineapple Slices: Pineapple brings a bright, tangy, and sweet tropical flavor. The reserved juice is crucial for moistening the cake mix and infusing it with even more pineapple goodness.

Yellow Cake Mix: Your convenient shortcut to a perfectly tender and fluffy cupcake base.

Vegetable Oil: A key fat source in the cake batter, vegetable oil contributes to a very moist and tender crumb. Unlike butter, oil remains liquid at room temperature, which often results in a cake that stays softer and moister for longer.

Eggs: Eggs are multi-talented! They provide structure to the cupcakes, helping them rise and hold their shape. They also add richness, moisture, and act as an emulsifier, binding all the ingredients together for a smooth, cohesive batter.

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How to Make Pineapple Upside-Down Cupcakes

Here's how to make these delightful Pineapple Upside-Down Cupcakes in just four simple steps. See the full recipe below for all the details.

1. Prepare Your Muffin Tins and Topping

Use nonstick regular-sized muffin cup (2 3/4-inches wide x 1 1/4-inches deep). This helps the cupcakes bake evenly and release easily. When assembling the topping in the muffin cups, place the cherry halves before the pineapple slices. This specific order ensures a beautiful, picture-perfect presentation when you flip the cupcakes.

2. Mix the Cake Batter 

In a large bowl, beat the yellow cake mix, reserved pineapple juice, vegetable oil, and eggs with an electric mixer for 2 minutes until well combined.

3. Fill and Bake 

An ice cream scoop is a fantastic tool for portioning the cake batter into muffin cups for a uniform in size and a consistent bake.

4. Cool and Serve

Let the cupcakes cool in the pan for 5 minutes. Remove and cool for an additional 20 minutes before serving warm.

How to Store Pineapple Upside-Down Cupcakes

To keep your delicious Pineapple Upside-Down Cupcakes fresh, simply store them loosely covered at room temperature. They will stay fresh for up to 3 days.

Pineapple Upside-Down Cupcakes

  • Prep Time 30 min
  • Total 1 hr 20 min
  • Servings 24
  • Ingredients 8
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Ingredients

  • 1/4 cup butter
  • 3/4 cup packed brown sugar
  • 12 maraschino cherries without stems, cut in half
  • 3 cans (8 oz) pineapple slices in juice, drained, juice reserved
  • 1 box Betty Crocker™ Super Moist™ Yellow Cake Mix
  • 1 cup reserved pineapple juice
  • 1/3 cup vegetable oil
  • 3 large eggs

Instructions

  • Step 
    1
    Heat oven to 350°F. Spray 24 nonstick regular-size muffin cups (2 3/4x1 1/4-inch) with cooking spray.
  • Step 
    2

    In a 1-quart sauce pan, melt butter. Stir in brown sugar. Place about 1 1/4 teaspoons brown sugar mixture in each muffin cup and spread evenly in bottom. Place a cherry half cut side up in the center of each cup. Cut each pineapple slice into 4 pieces. Place 2 pieces of pineapple around the cherry in the center and press lightly into the mixture.

  • Step 
    3

    In a large bowl, beat cake mix, reserved 1 cup pineapple juice, oil, and eggs with an electric mixer on medium speed for 2 minutes, scraping the bowl occasionally. Divide batter evenly among muffin cups.

  • Step 
    4

    Bake 19 to 23 minutes or until a toothpick inserted in the center comes out clean. Cool 5 minutes. Run a knife around the edges of the cupcakes to loosen and turn upside-down onto cookie sheet or tray. Cool about 20 minutes. Serve warm. Store loosely covered at room temperature.

Nutrition

160 Calories
6g Total Fat
1g Protein
26g Total Carbohydrate
18g Sugars

Nutrition Facts

Serving Size: 1 Cupcake
Calories
160
Calories from Fat
50
Total Fat
6g
9%
Saturated Fat
2g
10%
Trans Fat
0g
Cholesterol
30mg
9%
Sodium
130mg
5%
Potassium
55mg
2%
Total Carbohydrate
26g
9%
Dietary Fiber
0g
0%
Sugars
18g
Protein
1g
% Daily Value*:
Vitamin A
2%
2%
Vitamin C
2%
2%
Calcium
6%
6%
Iron
4%
4%
Exchanges:
1/2 Starch; 0 Fruit; 1 Other Carbohydrate; 0 Skim Milk; 0 Low-Fat Milk; 0 Milk; 0 Vegetable; 0 Very Lean Meat; 0 Lean Meat; 0 High-Fat Meat; 1 Fat;
Carbohydrate Choice
2
*Percent Daily Values are based on a 2,000 calorie diet.

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