Preheat your oven to 350°F (175°C) and line your cupcake pan with paper liners.
In a medium saucepan over medium heat, combine 1 cup of sweetened shredded coconut, 1 cup of packed dark brown sugar, and 1 cup of whipping cream. Stir until the mixture is thick and bubbly, about 5-7 minutes. Remove from heat and stir in 7 tablespoons of unsalted butter, 1 teaspoon of vanilla extract, and a pinch of salt. Set aside to cool.
In a large mixing bowl, whisk together 1 cup of coconut flour, 1 teaspoon of baking soda, and 1 teaspoon of salt. In another bowl, combine 1 cup of melted unsalted butter and 1 cup + 2 tablespoons of packed dark brown sugar, mixing until smooth. Add in 8 large eggs, 1 cup of whole milk, and 4 teaspoons of vanilla extract, whisking until fully incorporated.
Gradually add the dry ingredients to the wet mixture, stirring until just combined. Be careful not to overmix; a few lumps are okay!
Scoop the batter into the prepared cupcake liners, filling them about 2/3 of the way full. Bake in the preheated oven for 18-20 minutes or until a toothpick inserted into the center comes out clean. Allow them to cool in the pan for 5 minutes, then transfer to a wire rack to cool completely.
Once the cupcakes are completely cool, spoon the coconut topping generously over each cupcake.
In a double boiler or microwave-safe bowl, combine 1 cup of semi-sweet chopped chocolate with 6 tablespoons of whipping cream. Stir until the chocolate is melted and the mixture is smooth.
Using a spoon, drizzle the chocolate ganache over the frosted cupcakes, allowing it to cascade down the sides for a beautiful look.
