Level: Easy
Yield: 18 doughnuts
Nutritional Info Per Serving
Serving Size: 1 of 18 servings
Calories: 253 | Total Fat: 11 g | Saturated Fat: 5 g | Carbohydrates: 37 g | Dietary Fiber: 1 g | Sugar: 27 g | Protein: 2 g | Cholesterol: 31 mg | Sodium: 152 mg
Total Time: 1 hr 25 min
Active Time: 40 min

Ingredients

One 20-ounce can pineapple slices, reserving 1 teaspoon juice, drain the rest
1 1/2 sticks (12 tablespoons) unsalted butter
1 cup dark brown sugar
1 3/4 cups all-purpose flour (see Cook's Note)
1 cup granulated sugar
1 teaspoon baking powder
3/4 teaspoon kosher salt
1/2 teaspoon baking soda
1/2 cup buttermilk
1/4 cup vegetable oil
1/2 teaspoon vanilla extract
1 large egg
18 maraschino cherries, stems removed

Special Equipment

A nonstick metal doughnut pan and a large piping bag

Instructions

Preheat your oven to 375 degrees F. Get ready to create tropical paradise in every bite!
Carefully cut the pineapple rings in half horizontally to create thinner rings. Set asidethese will be your stunning topping.
In a small saucepan, melt the butter, then remove from heat and whisk in the brown sugar until fully combined. Spoon about a tablespoon of this luscious sugar mixture into each section of the doughnut pan, then press a pineapple slice firmly on top of each portion. Watch the magic begin!
In a medium bowl, whisk together the flour, granulated sugar, baking powder, salt, and baking soda. In another medium bowl, whisk the buttermilk, oil, vanilla, egg, reserved pineapple juice, and 1/4 cup water. Gently mix the wet ingredients into the dry until fully incorporatedsmooth and irresistible batter awaits.
Transfer the batter into a large piping bag or a gallon-size resealable plastic bag. Cut off a 3/4-inch corner and pipe the batter into the doughnut pan cavities, filling each nearly to the top. You're almost there!
Place the doughnut pan on a rimmed baking sheet and bake for about 10 minutes or until a toothpick inserted comes out clean. The aroma will have you drooling.
Allow the doughnuts to cool in the pan for 5 minutes, then loosen them with an offset spatula and invert onto a cooling rack. Golden perfection!
Garnish each doughnut with a maraschino cherry. Repeat the process with the remaining batter in two more batches. Share these pineapple upside-down delights and watch everyone rave!

Cook's Note

To measure flour correctly, spoon it into a dry measuring cup and level off the excess. Avoid scooping directly from the bag, as this compacts the flour and can lead to dry baked goods.