Preheat the oven to 350 degrees F (175 degrees C). Grease a 9-inch diameter, 2 1/2-inch tall round cake pan.
Stir brown sugar and melted butter together in a bowl. Spread evenly over the bottom of the prepared cake pan. Place pieces of pineapple on top of brown sugar mixture and around the outer edge of the pan, all facing the same way. Place 2 pieces in the center. Place a cranberry between each pineapple piece.
Beat white sugar and softened butter together using an electric mixer in a bowl until light and fluffy. Add eggs, one at a time, beating well and scraping the sides of the bowl after each addition. Pour in baking powder, vanilla extract, almond extract, cinnamon, and salt. Mix well.
Add 1/2 cup flour and 1/4 cup milk to batter at a time, mixing well after each batch until thoroughly blended.
Pour batter over pineapple slices, making sure batter gets between them. Spread and smooth batter using an offset spatula.
Bake in the preheated oven until a toothpick inserted into the center comes out clean, 40 to 45 minutes.
Remove cake from the oven and let cool on a wire rack for 15 to 20 minutes. Run a knife around the edges of the cake to loosen. Place a plate over the cake pan and quickly invert, waiting a few seconds for it to fall if it doesn’t immediately separate from the pan.
This is a very easy cake to make. A young person could make it with some parental guidance with the pineapple cutting and handling of the hot pan.
This cake is not as sickeningly sweet as some pineapple upside-down cakes and not as greasy because less butter and brown sugar are used to prepare the pan.
I use frozen cranberries or frozen pitted cherries instead of maraschino cherries, because I don’t like the taste or artificial coloring of the maraschino cherries. But something red on the cake makes this one still look traditional.
You can use canned sliced pineapple instead of fresh, and vanilla bean paste instead of vanilla extract.
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