Instructions

• Preheat oven to 350°F. Line a 12-cup muffin tin with cupcake liners and lightly spray the liners with non-stick spray (optional).
• Place 3 tablespoons coconut or canola oil, 1 stick unsalted butter (melted and slightly cooled), and 1/2 cup semi-sweet chocolate chips in a microwave-safe bowl. Microwave in 30-second increments, stirring between each, until the chocolate is fully melted and the mixture is smooth. (Or melt together over very low heat on the stovetop.) Set aside to cool slightly.
• In a medium bowl whisk together 3/4 cup plus 2 tablespoons all-purpose flour (not packed), 1/2 teaspoon baking soda, 1 teaspoon baking powder, 1/2 cup unsweetened cocoa powder, and 1/2 teaspoon salt. Set aside.
• In a large bowl whisk 2 large eggs plus 1 large egg yolk, 1 cup granulated sugar, and 1 teaspoon vanilla until smooth. Whisk in the cooled chocolate mixture until combined.
• Add half of the dry flour mixture to the wet mixture and stir just until incorporated. Add half of the 1/2 cup full-fat sour cream and stir to combine. Repeat with the remaining flour mixture and remaining sour cream, stirring until just combined. Do not overmix.
• Quickly stir in 1/2 cup hot coffee or hot water until evenly combined. Scrape batter into the prepared liners, dividing evenly among the 12 cups.
• Bake for 16–18 minutes, or until a toothpick inserted into the center comes out clean. Remove from oven and cool completely in the pan on a wire rack before filling and frosting.
• While cupcakes cool, make the coconut filling: in a small, heavy-bottomed saucepan combine 1 cup heavy whipping cream, 3/4 cup plus 2 tablespoons granulated sugar, and 1 stick butter (at room temperature). Heat over medium-high, whisking, until the sugar has dissolved and the butter has melted.
• Whisk 1 1/2 tablespoons cornstarch and 1 teaspoon vanilla extract into the hot cream mixture. Bring to a boil, whisking constantly, and continue cooking about 1 minute or until the mixture thickens. Remove from heat and stir in 4 ounces sweetened shredded coconut. Let the filling cool completely before using.
• Make the buttercream: beat 6 ounces unsalted butter (very soft) with 1 teaspoon vanilla extract until smooth. Gradually add 3 cups sifted confectioners' sugar, beating until well combined. Add 2 tablespoons coconut milk and beat until smooth.
• Divide the 7-ounce package sweetened flaked coconut in half. Fold one half of the flaked coconut into the buttercream; reserve the other half for topping.
• To assemble: when cupcakes are completely cool, cut a small hole or core out of the center of each cupcake. Spoon about 1 tablespoon of the cooled coconut filling into each hole.
• Top each filled cupcake with the coconut buttercream (pipe or spread). Sprinkle the remaining flaked coconut over the frosted cupcakes (use toasted or untoasted coconut if desired). Serve.