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1
For the cupcakes: Preheat the oven to 350 degrees F. Line one 12-cup standard muffin tin with cupcake liners.
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2
Whisk together the flour, granulated sugar, baking powder, milk, butter, vanilla, salt and egg in a medium bowl just until combined.
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3
Be careful not to over mix.
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4
Pour into the liners.
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5
Bake until a toothpick inserted in the center of the cakes comes out clean, about 18 minutes.
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6
Cool on a rack 10 minutes, and then remove the cupcakes and cool on the rack completely.
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7
For the filling: Melt the butter in a 10-inch nonstick skillet over medium heat.
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8
Add the pineapple, sugar and salt and cook, stirring frequently, until caramelized and the liquid is mostly evaporated, 18 to 20 minutes.
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9
(You will be able to run your spoon through the filling and leave a streak behind that holds 1 to 2 seconds before filling back in.
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10
The consistency of the filling should be like caramel sauce.)
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11
Set aside to cool.
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12
For the icing: Melt the butter in small saucepan over medium-low heat.
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13
Bring to a simmer and continue cooking until dark golden and toasty smelling, about 4 minutes.
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14
Once you see the milk solids turning a medium brown color, turn off the heat.
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15
Cool to room temperature.
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16
Whisk in the confectioners' sugar and pineapple juice to make it smooth but not too spreadable.
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17
To assemble: Using a melon baller, scoop out a hole in each cupcake large enough for 1 tablespoon of pineapple filling.
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18
Fill and press gently with the back of the spoon to level the filling.
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19
Spoon a teaspoon of icing over the hole to cover.
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20
Garnish the cupcakes as desired with cherries and pineapple.
