Preheat oven to 350°F (175°C). Grease a 9x13-inch baking pan.
Melt ¼ cup butter and pour it evenly into your baking dish. Sprinkle the brown sugar over the melted butter, spreading to cover the bottom.
Arrange the pineapple slices on top of the brown sugar, then place cherries in the centers of the pineapple rings and around them.
In a large mixing bowl, combine the cake mix, eggs, oil, and pineapple juice (or water). Mix on low speed until smooth. Gently pour the batter over the arranged pineapple and cherries.
Bake the cake for 40–45 minutes, or until a cake tester inserted into the center comes out clean.
Carefully run a knife around the edges of the pan to prevent sticking. Let the cake cool for about five minutes.
Place a large plate or cookie sheet over the pan, then carefully invert the cake (use oven mitts, it will be hot!). Let the pan rest on top for a few minutes so the brown sugar glaze can drip down.
Remove the pan, and your classic pineapple upside down cake is ready to serve!
Keyword pineapple upside down cake
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