Ingredients
Method
- Prepare Your Muffin Tin: First, preheat your oven to 350°F (175°C). Do not use paper liners. Grease a 12-cup muffin tin thoroughly with non-stick spray or butter, ensuring every crevice is coated.
- Create the Caramel Topping: Next, melt 1/2 cup of unsalted butter. Pour about a tablespoon of melted butter into the bottom of each greased muffin cup. Sprinkle about a tablespoon of packed light brown sugar evenly over the butter in each cup.
- Arrange Pineapple and Cherries: Take your well-drained pineapple rings, pat them dry. Cut some rings in half or quarters if needed to fit neatly into the bottom of each muffin cup. Place one piece of pineapple on top of the brown sugar in each cup. Center a drained, pat-dried maraschino cherry in the middle of each pineapple piece.
- Whisk Dry Ingredients: In a medium bowl, whisk together the 1 1/2 cups all-purpose flour (sifted for a lighter cake), 1 1/2 teaspoons baking powder, and 1/4 teaspoon salt. Set this aside.
- Cream Wet Ingredients: In a large mixing bowl, using an electric mixer, cream together 1/2 cup softened unsalted butter and 1/2 cup granulated sugar until light and fluffy, about 2-3 minutes. Beat in the large egg (room temperature) until well combined, then stir in 1 teaspoon vanilla extract.
- Combine Wet and Dry: Gradually add the dry ingredients to the wet ingredients, alternating with 1/2 cup milk (room temperature). Begin and end with the dry ingredients. Mix on low speed until just combined; do not overmix. A few small lumps are perfectly fine.
- Fill Muffin Cups: Carefully spoon the cupcake batter over the pineapple and cherry in each prepared muffin cup, filling each cup about two-thirds full. Be gentle to avoid disturbing the fruit and sugar layer underneath.
- Bake: Bake for 18-22 minutes, or until a wooden skewer inserted into the center of a cupcake comes out clean. The tops should be golden brown.
- Cool and Flip: Immediately after removing from the oven, let the Pineapple Upside Down Cupcakes cool in the muffin tin for only 5 minutes. This brief cooling period helps the caramel set slightly but prevents it from hardening too much and sticking.
- Invert: Place a wire cooling rack over the muffin tin. With oven mitts, carefully but quickly invert the entire muffin tin onto the cooling rack. The cupcakes should release easily. If any topping sticks, gently scrape it out and place it back on the cupcake. Let them cool completely on the rack, pineapple side up. Enjoy!
Notes
Pro Tips for Success:
Grease Generously: Ensure the muffin tin is exceptionally well-greased with non-stick spray or butter to prevent sticking, as caramel can be very sticky.
Pat Pineapple Dry: Thoroughly drain and pat dry canned pineapple rings to prevent excess moisture from making the caramel too runny.
Room Temperature Ingredients: Use room temperature egg and milk for better emulsification and a more tender, consistent cake texture.
Do Not Overmix: Mix the batter only until ingredients are just combined to avoid developing gluten, which can lead to tough cupcakes.
Act Quickly on Inversion: Invert cupcakes onto a cooling rack after only 5 minutes of cooling in the tin. Waiting too long can cause the caramel to harden and stick.
Even Batter Distribution: Use an ice cream scoop or measuring cup to ensure consistent baking and uniform cupcake sizes.
Use Quality Vanilla: Opt for pure vanilla extract or vanilla bean paste for a richer, more complex flavor.
Check Doneness: Test with a wooden skewer; if it comes out clean, the cupcakes are ready. Avoid overbaking to prevent dryness.
Storage & Reheating Tips:
Room Temperature: Store in an airtight container for 1-2 days. The high sugar content helps preserve them.
Refrigeration: For up to 3-4 days, store in an airtight container in the refrigerator to maintain freshness.
Freezing: Once completely cooled, wrap individually in plastic wrap and freeze in a freezer-safe bag for 2-3 months. Thaw overnight in the refrigerator or a few hours at room temperature.
Reheating: Gently reheat in the microwave for 10-20 seconds or in a preheated oven (300°F/150°C) for 5-7 minutes to re-melt the caramel and refresh flavors.
What to Serve With This Recipe:
Vanilla Ice Cream: A classic pairing that offers a cool, creamy contrast.
Whipped Cream: A light, airy dollop adds elegance.
Coconut Cream: A dairy-free, tropical alternative to whipped cream.
Fresh Berries: Raspberries, blueberries, or sliced strawberries add freshness and a slight tartness.
Mint Sprig: A garnish for color and aromatic freshness.
A Cup of Coffee or Tea: A comforting accompaniment for an adult indulgence.
Tropical Smoothie: Creates a complete tropical-themed treat experience.
Simple Glaze: A powdered sugar glaze with pineapple juice or milk adds extra sweetness and shine.