Pineapple Upside Cupcakes

Serves: 30 | Prep Time: 120 min | Cook Time: 10-20 min

Ingredients

Topping/Upside Down Ingredients

• 1-2 (15 oz) cans pineapple, sliced and drained
• 2/3 c brown sugar
• 1/3 c unsalted butter, melted
• 1 jar whole maraschino cherries, stems removed
• Cooking spray

 

Cake Ingredients

• 1 package Better Batter Gluten Free Yellow Cake Mix
• Pineapple juice from 1-2 cans (15oz) of pineapple, plus enough water to make 3/4 c total
• 3 eggs
• 1/2 c oil

 

Instructions

Preheat and prepare. Preheat the oven to 350 degrees. Spray a standard 12-well muffin pan or a 6-well jumbo muffin pan with cooking spray. Set aside.

 

Make the topping. Whisk together the brown sugar and melted butter. Divide the mixture evenly between the muffin tins. On top of the brown sugar mixture add a pineapple slice. To make it fit, cut out a wedge to make the ring smaller. For the jumbo cupcakes in this photo, I cut about 1/8 of the ring, but for smaller, standard muffin cups you may need to cut about 1/4 of the pineapple ring off. Make sure the pineapple sits flat in the bottom of the muffin pan wells. Add a maraschino cherry to the center of the pineapple. Set aside to prepare the cake mixture.

 

Prepare the cake mix. Using a large mixing bowl and a handheld mixer, combine the dry cake mix, eggs, oil, and 3/4 c pineapple juice. (If you do not have enough pineapple juice from the can, top off juice with water until you reach 3/4 cup.) Beat on low 30 seconds before increasing the speed to medium high and mixing until well incorporated, about 2 minutes. Be sure to scrape down the sides of the bowl with a spatula. Fill the wells of the prepared pan 3/4 full.

 

Bake. Bake the standard sized muffin pan for 18-22 minutes or a jumbo muffin pan 25-28 minutes or until a toothpick inserted in the center comes out clean. Remove from the oven and let cool 5 minutes in the pan. Carefully run a sharp knife around the edges to loosen the cake before inverting onto a plate or rack. Makes 8-14 cupcakes depending on which size you make.

 

This recipe was originally adapted from a Dole Recipe by Jennifer Lathom in June 2017. Updated 2025.  Original photo of food by Jennifer Lathom.