For the cupcakes:
About 21 (1.75-inch) round shortbread cookies*
6 tbsp. Dutch-process cocoa powder
6 tbsp. hot water
1½ cups all-purpose flour
½ tsp. baking soda
½ tsp. baking powder
½ tsp. salt
12 tbsp. (6 oz.) unsalted butter, at room temperature
1 cup plus 2 tbsp. sugar
2 large eggs, at room temperature
2 tsp. vanilla extract
½ cup sour cream
For the topping:
8 oz. bittersweet chocolate, finely chopped
½ cup caramel sauce**
½ cup heavy cream
1 tsp. coconut extract, divided
15 oz. soft caramels (store bought or homemade)
3 tbsp. milk
Pinch of coarse salt
3 cups sweetened shredded coconut, lightly toasted
Preheat the oven to 350˚ F. Line cupcake pans with paper liners. Place a shortbread cookie in the bottom of each liner. To make the cake, in a small bowl, combine the cocoa powder and hot water and whisk until smooth. In another medium bowl combine the flour, baking soda, baking powder, and salt, and whisk to blend.
Combine the butter and sugar in a medium saucepan set over medium heat. Cook, stirring occasionally, until the mixture is smooth and the butter is completely melted. Transfer the mixture to the bowl of an electric mixer and beat on medium-low speed until the mixture is cool, about 4-5 minutes. Add the eggs one at a time, mixing well after each addition and scraping down the sides of the bowl as needed. Blend in the vanilla and then the cocoa mixture until smooth. With the mixer on low speed, add the flour mixture in three additions alternating with the sour cream, beginning and ending with the dry ingredients and mixing each addition just until incorporated.
Divide the batter evenly between the prepared liners. Bake until a toothpick inserted in the center comes out clean, about 18 minutes, rotating the pans halfway through baking. Let cool in the pan about 5-10 minutes, then transfer to a wire rack to cool completely. When the cupcakes have cooled, level slightly if necessary (if large domes have formed.)
To make the ganache, place the chopped chocolate in a medium heatproof bowl. Combine the caramel and cream in a liquid measuring cup. Microwave in 30 second intervals and bring to a brisk simmer. (This can also be done in a saucepan.) Pour the warm liquid over the chocolate in the bowl and let stand 1-2 minutes. Whisk together until the chocolate is fully melted and a smooth ganache has formed. Stir in ½ teaspoon of the coconut extract. Spread a layer of the ganache on top of each cupcake.
To make the topping, place the caramels and milk in a large heatproof bowl. Microwave in 30 second intervals, stirring in between, until the mixture is melted and smooth. Stir in the salt and the remaining ½ teaspoon of coconut extract. Fold in the toasted coconut. Scoop a small mound of the coconut-caramel mixture (about 1½ tablespoons each) and place on top of each cupcake. If desired, indent the center of each mound to mimic the hole in a samoa cookie. When all the cupcakes have been topped, drizzle with any additional ganache. Let the ganache set before serving.
*I used the shortbread cookie dough from Kelly’s homemade samoa cookie recipe. You only need a half batch of dough for enough cookies for this recipe. If you use store bought cookies, you should be able to cut them to size with a small round cookie or biscuit cutter.
**Homemade caramel sauce is well worth your time. If you do use store bought, make sure it is of good quality and not overly sweet.