Food & Cooking Recipes Dessert & Treats Recipes Cake Recipes Pineapple Upside-Down Cake 3.8 (23) 1 Review By Martha Stewart Test Kitchen Martha Stewart Test Kitchen The recipes developed by our test kitchen team have undergone a rigorous process of development and testing, ensuring that every element is optimal, from ingredient amounts to method and cooking time. This process includes triple-testing recipes to ensure they meet our high standards. The many stellar cooks and food editors who have been part of our team include Sarah Carey, Lucinda Scala Quinn, Jennifer Aaronson, Shira Bocar, Anna Kovel, Greg Lofts, Riley Wofford, Lauren Tyrell, and Lindsay Leopold. Editorial Guidelines Updated on March 10, 2021 Print Rate It Share Share Tweet Pin Email Yield: Makes one 10 1/2-inch cake Martha's version of a classic pineapple upside-down cake uses dried tart cherries for maraschinos, and features a layer of thinly sliced fresh pineapple. Serve the cake in generous slices, with a dollop of rum-spiked whipped cream. Ingredients ½ cup dried tart cherries 1 pineapple, (about 3 ½ pounds), outer skin removed and uncored 1 cup cake flour 1 ½ teaspoons baking powder 1 ¼ cups granulated sugar 12 tablespoons (1 ½ sticks) unsalted butter, at room temperature ½ cup packed dark-brown sugar 1 vanilla bean, split lengthwise, seeds scraped 2 large eggs 6 tablespoons whole milk ½ teaspoon pure almond extract 1 cup heavy cream, well-chilled 2 tablespoons dark rum Directions Heat oven to 350 degrees. Line a baking sheet with parchment. Place cherries in a small heat-proof bowl. Bring 1 cup water to a boil in a small saucepan. Pour over dried cherries, and soak for 10 minutes. Drain well, and coarsely chop. Using a wide Japanese mandoline, slice whole pineapple as thinly as possible. Set aside. Sift together flour and baking powder. Set aside. Heat 1/2 cup of granulated sugar in a 10 1/2-inch cast-iron skillet. Cook until deep amber, about 5 minutes. Remove the pan from the heat. Add 4 tablespoons (1/2 stick) butter, stirring vigorously with a wooden spoon. Spread caramel evenly to coat the bottom of the skillet, and sprinkle with dark-brown sugar. Center one piece of pineapple in the skillet. Place pineapple slices in a tightly overlapping circle. Make a second ring, completely covering the bottom and continuing at least halfway up the sides. Place one remaining slice in the center of the skillet on top of the circles. (Be certain that there are no gaps as the bottom will be the top upon inversion). In a heavy-duty mixer fitted with the paddle attachment, cream remaining butter, remaining 3/4 cup of granulated sugar, and vanilla-bean scrapings. Add eggs one at a time, mixing well after each addition. Pour in milk and almond extract. Slowly add sifted flour, scraping sides as needed. Using a rubber spatula, fold in chopped cherries. Pour batter into pineapple-lined skillet. Spread batter evenly with an offset spatula. Place skillet on a prepared baking sheet, and transfer baking sheet to oven. Bake until golden brown and cake tester comes out clean, about 45 minutes. Meanwhile, pour cream into the bowl of a heavy-duty mixer. Add rum. Whip on high speed until stiff peaks form, 45 to 60 seconds. Remove cake from oven, and pour excess liquid from skillet into a measuring cup. Carefully invert onto large cake plate, and pour reserved liquid over cake. Serve with rum-spiked whipped cream. Rate it Print