Pineapple Upside Down Cupcakes Recipe

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

5 from 52 votes

Pineapple Upside Down Cupcakes Recipe

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

Prep Time10

Cook Time20

Total Time30

Course: Dessert

Cuisine: American

Servings:

Author: Kristyn Merkley

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.

Video

Notes

Recipe Tips.

Spray the muffin tin very well to help the caramel topping release cleanly after baking.
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.
If you wish, you can cut small rounds out of parchment paper to add to the bottom of each cupcake well.
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.
These cupcakes can be made a day ahead and stored covered at room temperature or reheated slightly before serving.
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.
I don't recommend lining the muffin cups with paper cupcake liners; however, you can use reusable silicone liners.
The yellow cake mix can be substituted with a pineapple cake mix.

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.

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