Pineapple Upside Down Cake

Ingredients

• 4 tbsp unsalted butter – for topping
• 0.75 cup light brown sugar
• 20 ounces canned pineapple rings – drained
• 12 pieces maraschino cherries – drained and patted dry
• 1.5 cups all-purpose flour
• 1.5 tsp baking powder
• 0.5 tsp kosher salt
• 0.5 cup unsalted butter – room temperature
• 1 cup granulated sugar
• 2 pieces large eggs
• 1 tsp vanilla extract
• 0.5 cup whole milk – room temperature
• 0.25 cup pineapple juice (reserved from can)

Instructions

1. Preheat the oven to 350°F. Place a 9-inch round cake pan (at least 2 inches deep) on a sheet pan for easy handling.
2. Add 4 tbsp unsalted butter (for topping) to the cake pan and place in the oven just until melted, 3–5 minutes. Remove, swirl to coat the bottom, and sprinkle the light brown sugar evenly over the melted butter.
3. Drain the canned pineapple rings, measuring and reserving 0.25 cup of the juice for the batter. Arrange the pineapple rings over the brown sugar in a single layer, cutting and fitting pieces as needed to cover the surface. Nestle the maraschino cherries in the centers of the rings and any gaps.
4. In a medium bowl, whisk together the all-purpose flour, baking powder, and kosher salt.
5. In a large bowl, beat 0.5 cup room-temperature unsalted butter with the granulated sugar using a hand mixer or stand mixer on medium speed until light and fluffy, 2–3 minutes.
6. Beat in the large eggs one at a time, then mix in the vanilla extract until smooth.
7. Stir together the whole milk and the reserved pineapple juice. Add the dry ingredients to the butter mixture in two additions, alternating with the milk-juice mixture, beginning and ending with the dry. Mix on low just until combined; do not overmix.
8. Dollop the batter over the fruit and gently spread to the edges, taking care not to disturb the arrangement.
9. Bake until the top is golden brown, the edges are bubbling, and a toothpick inserted in the center comes out with a few moist crumbs, 40–45 minutes.
10. Cool in the pan on a rack for 15 minutes. Run a thin knife around the edge, invert a serving plate over the pan, and flip to release the cake. Carefully lift off the pan.
11. Let cool at least 30 minutes more before slicing. Serve warm or at room temperature.