These gluten-free pineapple upside down cupcakes, made with Namaste Gluten-Free Flour, are moist, fluffy and topped with a buttery brown sugar syrup. The recipe makes a perfect dozen so you can enjoy them a few bites at a time.
Just like a pineapple upside down cake these cupcakes start with a melted butter and brown sugar mixture at the bottom of the pan. This yummy buttery syrup is absorbed into the outside of the cake and gives it the most wonderful buttery flavor.
Traditionally pineapple upside down cakes also use a maraschino cherry in the center of each pineapple ring. I’m not a fan of maraschino cherries or the artificial colors in them. So I bake them without the cherry and top with fresh berries once cooled. See more topping options below.
Arrange pieces of pineapple rings on the brown sugar syrup to create a beautiful glistening topping on these cupcakes. Pineapple rings are too large to fit in a standard sized cupcake pan, so I cut them in quarters and use two per cupcake.
Canned pineapple rings are really the best way to go. Use pineapple rings packed in pineapple juice, not heavy syrup. You could cut up your own pineapple but the canned rings make it super easy and fast. The whole rings don’t fit in a standard muffin tin so you’ll cut them into pieces to make them fit.
Pineapple juice – a little bit of the juice from the canned pineapples will go into the cake batter to add natural sweetness.
Oil is my preferred way to add moisture to gluten-free cakes, cupcakes and muffins. It holds up better over a day or two – better than butter. Butter has more water content which tends to evaporate. So even though I enjoy the flavor of butter more, I stick with oil to keep these cupcakes moist and fluffy. And the butter brown sugar syrup will seep in to the cupcakes and give them a buttery flavor
The rest of the ingredients in these cupcakes are just the basics – eggs, milk (dairy free okay), baking powder, salt & vanilla to bring it all together.
- After the cupcakes are cooled, top them with a fresh raspberry or any other fresh berry you’ve got in the fridge.
- Add more tropical flavor to these cupcakes with a sprinkling of shredded coconut.
- Add more caramel flavor with a delicious apple caramel sauce drizzle.
Gluten-Free Namaste Flour Pineapple Upside Down Cupcakes
- #30 (2.3 Tbsps) scoop optional
- 6 pineapple rings, packed in pineapple juice reserve 1 Tbsp juice
- ⅓ c packed, light brown sugar
- 4 Tbsp unsalted butter, cut into 4 pieces
- ¼ tsp vanilla extract, powder or bean paste
- ¼ tsp salt
- 6 maraschino cherries cut in half (optional)
- ¾ c + 1 Tbsp Namaste Gluten-Free Flour
- 2 tsp baking powder
- ¼ tsp salt
- ⅓ c sugar
- 2 large eggs
- ⅓ c milk or dairy-free milk sub
- ¼ c oil – avocado, sunflower, canola or other neutral flavored vegetable oil
- 1 Tbsp pineapple juice from the canned pineapple
- ½ tsp vanilla extract, powder or bean paste
- Preheat the over to 350°F. The butter/brown sugar syrup may seep out during baking, so place a sheet pan or foil on a lower rack or the bottom of the oven. Generously grease a cupcake pan with oil spray or butter.
- This recipe can easily be mixed up with a wire whisk. No electric mixer is necessary.
- Remove 6 pineapple slices from the can and lay on an absorbent towel. Cut each ring into 4 pieces.
- Place the brown sugar and water in a small skillet over low heat. Stir until the brown sugar is melted – at least 1½ minutes.
- Add the butter, vanilla and salt and turn up the heat to low-medium. Stir constantly for another 2-3 minutes or until the butter combines with the sugar syrup. The butter will remain on the top for a while, but will eventually incorporate.
- Immediately add 2 tsps of the syrup to the pan, for each cupcake. If using, place a half maraschino cherry in the center, cut side facing up.
- Place 2 pieces of pineapple on top of the syrup and cherry
- Combine the flour, baking powder and salt in a medium sized mixing bowl.
- In a small mixing bowl, beat the sugar, eggs, milk, oil, pineapple juice, and vanilla until creamy.
- Pour the liquid into the flour mixture and stir with a wire whisk just until smooth.
- Distribute the batter evenly in the cupcake pan. It is a little more than 2 Tbsp per cupcake. The scoop linked above works well.
- Bake for 20-23 minutes or until the top is set and it bounces back from a very gentle tap.
- Cool the cupcakes in the pan for 10 minutes. Then run a knife gently around the outside edge of each cupcake to loosen.
- Place a cooling rack, upside down on top of the cupcake pan.
- Place an inverted sheet pan on top of the cooling rack. This will catch any syrup that may spill out when you flip the cupcakes out.
- Flip all of it over and let sit for another 3-4 minutes.
- Tap a couple of times on the inverted pan, a few times on each cupcake. Use one hand on each side of the pan, lift it up just a half inch and hold for a few seconds. The cupcakes should drop out of the pan and onto the cooling rack. If any remain, gently twist the cupcake to loosen and remove from the pan.
- Let cool at least another 10 minutes, if serving warm, or until at room temperature.
- These cupcakes are best if used within one day. Refrigerate after 24 hours.