Preheat oven to 350 degrees and melt butter in two separate dishes.
Mix together 2 tablespoons melted butter with 1/4 cup of brown sugar. Divide equally amongst 4 large ramekins. Add a pineapple ring to each ramekin, and place a cherry in the center of each pineapple. Set aside.
2 tablespoons unsalted butter, 1/4 cup brown sugar, 4 pineapple rings, 4 maraschino cherries
In a box, whisk together the buttermilk and egg, adding the brown sugar and whisking again. Add vanilla and butter and whisk to incorporate. Add baking soda and salt, mixing until combined. Add flour and stir gently until just incorporated.
1/4 cup buttermilk, 1 egg, 1/3 cup brown sugar, 1/4 teaspoon vanilla, 3 tablespoons unsalted butter, 1/8 teaspoon baking soda, pinch salt, 2/3 cup flour
Pour batter evenly amongst each of the four ramekins. Place ramekins on a baking sheet and place entire baking sheet in the oven at 350 degrees for 25-27 minutes, until a cake tester comes out with just a few crumbs.
Let cool 10 minutes, then run a knife around the edge of each ramekin and turn the mini pineapple upside down cakes out onto plates for serving.
If you do not have a 1/8 teaspoon measure, use your 1/4 teaspoon and ensure you only fill it halfway.
These cakes also freeze nicely for an on-call dessert later. Once fully cooled, wrap tightly in tin foil and freeze up to a month. When ready to enjoy, reheat in a 170 degree oven, still wrapped, for 10-12 minutes and serve immediately.
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