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Classic Pineapple Upside Down Cake

1 can (20 Oz Can) Pineapple Rings With Syrup (you'll Be Using About 6-7 Rings)
4 Tablespoons Unsalted Butter
23 cups Packed Brown Sugar
7 whole Maraschino Cherries, Drained Of Their Syrup
1- 1/2 cup All-purpose Flour
3/4 cups Vanilla Sugar
1- 1/2 teaspoon Baking Powder
1/2 teaspoons Sea Salt
3/4 cups Room Temperature Whole Milk
2 Tablespoons Reserved Pineapple Syrup
1 teaspoon Vanilla Extract
4 Tablespoons Unsalted Butter, Room Temperature
1 whole Egg, Room Temperature


Makes one 9 round cake. 1. Preheat the oven to 350 degrees F and get out your 9 cake pan. Using the butter wrapper (or some butter or non-stick spray), lightly grease the bottom and sides of your pan. Set aside. Also, drain the pineapple rings well and reserve 2 tablespoons of the syrup for your cake batter. Set aside. 2. In a small sauce pot add your first 4 tablespoons of butter. Melt over medium-low heat until just melted. I opted to go a little further and browned it slightlyit was delicious! Pour melted butter into the bottom of your lightly greased cake pan. Next, sprinkle your brown sugar over the butter. Finally, place the pineapple rings onto the brown sugar/buttered bottom and arrange so that it is one nice even layer of pineapple rings. Add one maraschino cherry into the middle of each ring and set pan aside. 3. Into the bowl of your stand mixer, add your flour, vanilla sugar, baking powder and salt. With a paddle attachment, mix on low to combine. 4. In another bowl or large measuring cup, mix together your milk, reserved pineapple syrup, and vanilla extract. Add the milk mixture and your butter into the flour mixture and beat on medium-low speed until combined. Stop and scrape down sides and bottom of bowl and beat another 1-2 minutes on medium (or until smooth). 5. Finally, add your egg and beat for another 1-2 minutes, making sure to stop and scrape sides and bottom of bowl once more. 6. Carefully pour cake batter into your prepared cake pan, making sure to spread evenly over the pineapple and cherries (but not disrupting them too much). Pat the pan on the counter a few times to settle the batter even further. 7. Bake at 350 degrees F for 35-40 minutes or until the cake is golden brown along the sides, the middle springs back when gently pressed and a toothpick inserted into the middle (but not through to the very bottom) comes out clean. Remove pan from oven and set it on a rack. Cool the cake for 5 minutes in the pan and then carefully (with oven mitts) turn it out onto a cake platter or plate. I did this by flipping my cake stand upside down, placing it over the top of the cake pan and then carefully pressing the two together, flipping the bottom of the cake pan over, so its now the new top. Then, gently remove the cake pan. Your pineapples and cherries should be beautifully displayed on the top of your cake, with syrup dripping down. Yum! Serve warm with vanilla ice cream or whipped cream or cool to room temperature! Adapted from Nancie McDermotts Southern Cakes.

Source: tastykitchen.com