Pineapple Upside Down Cupcakes

Name: Pineapple Upside Down Cupcakes Recipe
Prep time: 10 min
Cook time: 20 min
Total time: 30 min
Ingredients: 1 (20-ounce) can pineapple rings (drained and juice reserved); 1 (15.25-ounce) box yellow cake mix; ½ cup vegetable oil; 3 eggs; ⅓ cup butter (melted); ⅔ cup brown sugar (packed); 12 maraschino cherries (cut in half)

Pineapple Upside Down Cupcakes are the cutest little twist on the classic cake, and they are always a hit! Each one has that buttery brown sugar topping, sweet pineapple, and a bright cherry right in the center, all baked into perfectly portioned cupcakes.

What makes these so great is how easy they are, thanks to a cake mix shortcut, but they still look like you spent a lot of time in the kitchen. They are perfect for parties, potlucks, holidays, or anytime you want a fun dessert that serves itself.

If you love easy, nostalgic desserts like this, you should also try Easy Pineapple Upside Down Cake, Strawberry Shortcake Bars, and Lemon Bars.

Why we think you’ll love it:

Shortcut friendly. Starts with a cake mix, so you can make a homemade style dessert with very little prep time.
Perfect for gatherings. Individual cupcakes are easy to serve at parties, potlucks, or family dinners.
Reliable results. This tested recipe turns out soft, moist cupcakes that look impressive but are simple to make.

Pineapple Upside Down Cupcake Ingredients

Pineapple rings (1 twenty ounce can, drained and juice reserved): Adds juicy sweetness and that signature tropical flavor. The reserved juice is used in the batter for extra moisture and flavor.
Yellow cake mix (1 fifteen point twenty five ounce box): Creates a soft, fluffy cupcake base with consistent results. We like classic brands like Betty Crocker or Duncan Hines. Pineapple cake mix can also be used.
Vegetable oil (½ cup): Keeps the cupcakes moist and tender even after they cool. You can substitute canola oil if needed.
Eggs (3): Provides structure and richness, helping the cupcakes rise properly and hold their shape.
Butter melted (⅓ cup): Combines with brown sugar to form the caramelized topping that gives these cupcakes their classic upside down flavor.
Brown sugar packed (⅔ cup): Adds deep sweetness and creates that gooey, buttery glaze as the cupcakes bake. Light or dark brown sugar both work.
Maraschino cherries (12, cut in half): Brings bright color and a sweet pop of flavor that makes each cupcake feel festive and fun.

How to Make Pineapple Upside Down Cupcakes

Putting pineapple and cherries in the bottom of a cupcake tin.

PREP. Preheat the oven to 350°F. Prepare 24 wells of a muffin tin by spraying with cooking spray.

CAKE. In a large bowl, mix the pineapple juice, yellow cake mix, oil, and eggs until well blended.

FRUIT. Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.

BAKE. Pour the cake batter into the cupcake tin, filling to about ¼ inch from the top. Bake 20-25 minutes, or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.

Serve warm with freshly Whipped Cream, if desired.

Top view of pineapple upside down cupcakes topped with pineapple and a cherry.

Kristyn’s Recipe Tips

Spray the muffin tin very well to help the caramel topping release cleanly after baking.
Cut the rings into smaller sections, or buy a 20-ounce can of pineapple chunks, or even use crushed pineapple or pineapple tidbits.
The amount of pineapple juice should be equal to 1 cup. If you are shy, add water to the juice to get 1 cup.
Use a sharp paring knife or a small rubber spatula and slide it around each cake, releasing the sides from the pan. Flip the cupcake pan onto wax paper. Allow the cupcakes to sit for another few minutes with the pan still covering them. The cakes should begin to plop down on their own. Carefully remove the pan.
Do not overfill the wells since the cupcakes will rise and could spill over.
Let cupcakes cool slightly before inverting so the topping sets but is still warm enough to release.

5 from 52 votes

Pineapple Upside Down Cupcakes Recipe

By: Kristyn Merkley

Pineapple Upside Down Cupcakes are easy cake mix cupcakes with buttery brown sugar topping, pineapple, and cherries, perfect for parties and potlucks.

Servings: 24

Prep: 10

Cook: 20

Total: 30

Video

Ingredients

▢ 1 (20-ounce) can pineapple rings drained and juice reserved
▢ 1 (15.25-ounce) box yellow cake mix
▢ ½ cup vegetable oil
▢ 3 eggs
▢ ⅓ cup butter melted
▢ ⅔ cup brown sugar packed
▢ 12 maraschino cherries cut in half

Instructions

Preheat the oven to 350°F. Prepare 24 wells of a muffin tin by spraying with cooking spray.
In a large bowl, mix together the pineapple juice, yellow cake mix, oil, and eggs until well blended.
Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.
Pour the cake batter into the muffin tins, filling to about ¼ inch from the top. Bake 20-25 minutes or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.
Serve warm with freshly whipped cream, if desired.

Notes

Recipe Tips.

Do not overfill the wells since the cupcakes will rise and could spill over.
Let cupcakes cool slightly before inverting so the topping sets but is still warm enough to release.
Use kitchen shears to quickly cut pineapple rings into even pieces for easier assembly.
Cut the rings into smaller sections, or buy a 20-ounce can of pineapple chunks, or even use crushed pineapple or pineapple tidbits.
The amount of pineapple juice should be equal to 1 cup. If you are shy, add water to the juice to get 1 cup.

Store. Store the pineapple upside down cake cupcakes in the fridge, in an airtight container, for about 3 days.

Freeze. Allow the cupcakes to cool and flash freeze by placing them in the freezer for about an hour. Take the cupcakes out, wrap them with plastic wrap, then again with foil.

Or place the wrapped cupcakes in a freezer-safe container. Label and freeze for 2-3 months.

Nutrition

Calories: 192kcal, Carbohydrates: 28g, Protein: 1g, Fat: 8g, Saturated Fat: 2g, Cholesterol: 27mg, Sodium: 189mg, Potassium: 55mg, Sugar: 19g, Vitamin A: 120IU, Vitamin C: 2.2mg, Calcium: 59mg, Iron: 0.7mg

Nutrition information is automatically calculated, so should only be used as an approximation.

Recipe FAQ

How to store?

Store the pineapple upside down cake cupcakes in the fridge, in an airtight container, for about 3 days.

How to freeze?

Allow the cupcakes to cool and flash freeze by placing them in the freezer for about an hour. Take the cupcakes out, wrap them with plastic wrap, then again with foil.
Or place the wrapped cupcakes in a freezer-safe container. Label and freeze for 2-3 months.