1. Preheat oven to 400 degrees F
2. Grease mini doughnut pan. In a small bowl, mix well-drained pineapple with brown sugar. Pour 1/8 teaspoon melted butter into each section of the mini doughnut pan. Place 3 pieces of cherries into each doughnut well. Add about 1/2 teaspoon of brown sugar coated pineapple to each doughnut section (avoid adding the sugary juice that might form in the bowl with the pineapple).
3. In a large bowl, beat the butter with the sugar with a mixer. Beat in the egg and vanilla extract. By hand, stir in the baking powder, cinnamon, and salt. Stir each of the following into the butter/sugar mixture in the bowl, being sure to incorporate each addition before adding the next: 1/3 of the flour, then add half of the milk, following by another 1/3 of the flour, the remainder of the milk, and then the remainder of the flour.
4. Place batter in a zipper-style plastic bag, seal, and snip off a small bit of one corner (or place in a pastry bag), and squeeze the batter on top of the fruit in the pan. You’ll want to cover all the fruit with batter, but avoid covering all the way to the edge of each well.
5. Bake for 5-7 minutes or until a toothpick inserted in a doughnut comes out clean. Remove doughnuts from oven and allow to cool in pan for about 5 minutes. Turn them out onto a cooling rack to continue cooling.

Pineapple Syrup: While donuts are baking, heat and stir together 1/2 cup of reserved pineapple + 1 cup sugar in a saucepan over medium heat. Heat until sugar is dissolved and syrup is thickened, remove from heat and allow to cool slightly.

1. When doughnuts are able to be handled, dip the tops (fruit side) of the doughnuts into the syrup and place back onto cooling rack to continue cooling and to allow any excess to drip off.