Hundred Dollar Cupcakes with Caramel Icing

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Cupcakes:

2 cups cake flour, sifted before measuring

1 1/2 teaspoons baking powder 

3/4 teaspoon salt 

1/2 teaspoon baking soda 

4 ounces unsweetened chocolate, chopped 

1 cup granulated sugar 

1 cup light brown sugar 

1 stick (8 tablespoons) unsalted butter, softened 

2 large eggs, at room temperature 

2 teaspoons vanilla extract 

1 1/2 cups whole milk, at room temperature 

Icing:

2 cups granulated sugar

3/4 cup buttermilk 

1 stick (8 tablespoons) unsalted butter 

1 teaspoon baking soda 

1 teaspoon vanilla extract 

Splash of heavy cream, if needed

Edible silver dragees, for decorating