Preheat oven to 350 degrees F. Line a muffin pan with paper liners.
In a small saucepan, combine the milk, shredded coconut and coconut milk powder. Bring just to a simmer over medium low heat. Remove from the heat and set aside to infuse for at least 30 minutes.
1 1/2 cup milk, 1/2 cup coconut, 2 tbsp coconut milk powder
In a medium bowl, whisk together the flour and cocoa powder, set aside.
2 cup cake flour, 3/4 cup cocoa powder
In a large mixing bowl, cream together the butter, sugar, salt, baking soda, vanilla, and coconut extract until fluffy and light.
Add the eggs to the butter mixture one at a time, beating well after each addition.
4 eggs
Slowly blend one third of the flour mixture into the creamed mixture, then half the milk and coconut mixture, another third of the flour, the remaining milk and coconut, and, finally, the remaining flour. Be sure to scrape the sides and bottom of the bowl occasionally throughout this process.
Increase the mixer speed to medium high for about 1 minute, this will help develop the structure. Scoop the batter into each liner, filling about 1/2 full (do not overfill the liners or the batter will spill out over the top of the cups).
Bake for 20-22 minutes, or until a toothpick comes out with a few moist crumbs. Remove from the oven. Tilt each cupcake in the muffin pan so it sits at an angle. Cool like that for 10 minutes, then remove them to a cooling rack to finish cooling.
For the filling:
Heat the dulce de leche in the microwave in 20-30 second intervals, mixing after each interval, until it is smooth and slightly thinned.
2 cups dulce de leche
Combine the toasted coconut with the dulce de leche.
1 1/2 cups unsweetened coconut
Fill a piping bag fitted with a wide tip with the caramel and coconut mixture.
Press the tip of the piping bag into the center of each cupcake and pipe about 1 1/2 to 2 tbsp of the mixture into the cake. Be careful not to overfill the cake as it will crack and break.
For the Frosting:
Melt the butter in a heavy 2-quart saucepan.
1 cup unsalted butter
Stir in the salt and brown sugar and heat the mixture to boiling, stirring constantly.
1/2 teaspoon salt, 2 cup brown sugar
Cook over low heat for 2 minutes, until the sugar is totally dissolved. Stir in the milk and return to a boil, stirring constantly.
1/2 cup milk
Remove the pan from the heat and cool to lukewarm (30-40 minutes) stirring occasionally.
Stir in the vanilla, then gradually beat in the powdered sugar using an electric mixer. Adjust consistency with a little more milk or sugar, if necessary. The frosting should be smooth, creamy and thick enough to hold its shape when piped.
2 teaspoon vanilla extract, 5 cup powdered sugar
Pipe the frosting onto the cooled cupcakes.
For the topping:
Put the toasted coconut into a wide, shallow dish. Invert each cupcake, press the top lightly into the toasted coconut - the frosting should flatten slightly and an even layer of coconut will adhere to the top. Place the cupcakes upright on the cooling rack again. (you will have leftover toasted coconut, the 1 cup is to ensure enough depth to dip all of the cupcakes)
1 cup toasted coconut
Place the chocolate in a heat proof bowl.
4 ounce dark chocolate
Bring the cream to a simmer, pour over the chocolate and let stand for about a minute. Whisk until smooth.
3 tablespoon heavy cream
Immediately whisk in the butter, just until incorporated.
1 tablespoon unsalted butter
Allow mixture to cool slightly, then drizzle or pipe stripes over the top of the cupcakes. Store the cupcakes in an airtight container at room temperature.
Notes
Cupcake liners: Use standard paper cupcake liners for this recipe. Decorative liners made from thicker, stiffer paper don’t make full contact with the pan, which prevents the batter from baking evenly.
Coconut texture varies by brand: Different brands — and different shred sizes within the same brand — will produce different textures when mixed with the caramel. If your filling becomes too stiff, add heavy cream 1 tablespoon at a time until it reaches a soft, creamy consistency.
Sweetened vs. unsweetened coconut: Sweetened shredded coconut behaves very differently from unsweetened. It doesn’t absorb liquid and can actually loosen mixtures. If you only have sweetened coconut, you can still make the filling, but either reduce the dulce de leche to 10 oz or increase the coconut to 1 1/2 cup to keep the texture balanced.