Preheat the oven to 350ºF. Place cupcake holders on a medium-sized cookie sheet; set aside.
Melt chocolate in a small bowl placed over a small saucepan of simmering water. Let cool 5 minutes. In a small bowl, combine wine and milk; set aside.
In the bowl of an electric mixer fitted with the paddle attachment, beat the butter and the granulated sugar on medium speed until light and fluffy. Add eggs; beat for 2 minutes. Add the cooled chocolate mixture and beat until incorporated, scraping down the sides of the bowl as necessary.
In a large bowl, whisk flour, gelatin, cocoa powder, baking powder, baking soda, and salt to combine. Add to mixer bowl, along with the wine mixture, and beat on low speed until combined, about 1 minute. Increase the speed to medium and beat for 2 minutes more, scraping down the sides of the bowl as necessary. Spoon batter into prepared cups.
Bake for 20-25 minutes, or until a toothpick inserted into the center of the cake comes out clean. Cool completely before decorating.
To make the glaze:
Combine the butter, wine, and confectioners' sugar in a medium saucepan. Bring to a boil, stirring occasionally, over medium-high heat. Remove from heat; stir in vanilla. Use a fork to make holes in the cupcakes and using a small spoon, sprinkle a small amount of glaze onto each.
To make the frosting:
Ensure the cream is properly chilled - chilling the mixer bowl also helps. Pour the cream into the bowl of an electric mixer and sprinkle in the crushed vanilla beans. Whip the cream on high setting, adding the icing sugar until firm peaks are achieved. Use a piping bag and a
#885 tip to pipe swirls onto the cupcakes.
Notes
cake and glaze recipes adapted from Martha Stewart