Step 1

Preheat the oven to 350°F (175°C). Line two 12-cup muffin tins with cupcake liners.

Step 2

In a medium bowl, whisk together the flour, baking powder, salt and baking soda.

Step 3

Put the chocolate in a microwave-safe bowl and microwave on high in 30-second intervals, stirring after each, until melted, about 1 1/2 minutes total (or melt it in a double boiler).

Step 4

In the bowl of a stand mixer fitted with the paddle attachment, beat the granulated sugar, brown sugar and butter until light and fluffy, about 3 minutes. Add the melted chocolate and beat to combine. Add the eggs one at a time, beating well after each addition. Beat in the vanilla. Add the flour mixture in three batches, alternating with the milk, beginning and ending with the flour, and beat on low until just combined.

Step 5

Divide the batter evenly among the prepared muffin tins, filling each cupcake liner with about 1/4 cup of the batter. Bake until the cupcakes are domed slightly and a toothpick inserted into the center comes out clean, about 18 minutes. Let cool completely on a wire rack.

Step 6

Make the icing right before you are ready to make the cupcakes. In a medium to large heavy- bottomed saucepan, combine the granulated sugar, buttermilk, butter, baking soda and vanilla (the liquid will double in volume, so be sure your pan is large enough). Clip a candy thermometer to the side of the pan and bring the mixture to a boil over medium-high heat. Boil until the mixture reaches soft-ball stage (235°F/112°C), 10 to 15 minutes. Remove from the heat as it hits the soft-ball stage to avoid overcaramelizing.

Step 7

Working very quickly, but carefully, pour the caramel into the bowl of a stand mixer fitted with the paddle attachment and beat on medium-high speed until cooled to warm, about 5 minutes. Working quickly, spoon about a tablespoon of the caramel icing onto each cupcake. (Caramel hardens a little as it cools. Whip in a splash of cream to loosen it up if needed.) Let stand until set, about 5 minutes, before serving.

Step 8

Makes 24 cupcakes.

Step 9

Adapted from Trisha's Kitchen: Easy Comfort Food for Friends and Family, by Trisha Yearwood with Beth Yearwood Bernard (Mariner Books 2021)