Preheat your oven to 350°F and line a baking sheet with parchment paper. On the sheet, combine the raw pecans, 2 tablespoons bourbon, 1 teaspoon vanilla extract, 2 tablespoons packed brown sugar, and 1/2 teaspoon ground cinnamon. Toss well and bake for 8-10 minutes until the pecans are toasted and aromatic. Once done, sprinkle with sea salt if you wish. Roughly chop the pecans, saving 22 whole pecans for garnishing later.

In a large pot off the heat, whisk together the egg yolks, cornstarch, and 1 tablespoon water until smooth. Then whisk in 1/2 cup packed brown sugar, the maple syrup, and a pinch of kosher salt. Place the pot over medium-high heat and bring to a gentle boil, stirring constantly. Continue stirring for 5-8 minutes until the mixture thickens noticeably. Remove from heat, strain through a fine mesh sieve into a heatproof bowl, and stir in about 1 cup of the chopped toasted pecans (from Step 1) and 2 teaspoons vanilla extract. Cover and chill in the refrigerator until set, about 1 hour. I recommend tasting the filling at this point and adjusting the salt if needed – a tiny pinch brings out the nutty flavor beautifully.

Preheat the oven to 350°F again if needed and line 20-22 cupcake molds with paper liners. In the bowl of a stand mixer (or using a hand-held mixer), beat together the melted coconut oil (cooled slightly), 1/2 cup bourbon, strong black coffee, 2 large eggs, Greek yogurt, and granulated sugar until smooth. Add in the flour, cocoa powder, baking soda, and 3/4 teaspoon kosher salt. Mix until you have a smooth batter with no lumps. Divide the batter evenly among the prepared cupcake liners, filling each about two-thirds full. Bake for 18-22 minutes until the tops are just set and no longer wiggly in the center. Remove from the oven and allow the cupcakes to cool before filling.

In a medium saucepan over medium heat, melt together 4 tablespoons salted butter, the heavy cream, and 1 cup packed brown sugar. Stir until the butter is melted and the sugar has dissolved. Bring to a boil and cook for about 1 minute. Pour the hot mixture into the bowl of a stand mixer (or a large mixing bowl) and refrigerate (or freeze for 15-20 minutes) until cool to the touch. I like using high-quality butter for extra creamy frosting.

Retrieve the cooled butter mixture from the fridge or freezer. Add the remaining 12 tablespoons salted butter, 1 tablespoon vanilla extract, and sifted powdered sugar. Beat together with an electric mixer until smooth and fluffy. Gently fold in 1/2 to 1 cup of the finely chopped toasted pecans (from Step 1) to give it texture and flavor.

Once the cupcakes and filling are cooled, use a paring knife to cut a cone-shaped piece out of the center of each cupcake. Spoon the chilled pecan pie filling (from Step 2) into each hole. Frost the tops of the cupcakes generously with the prepared pecan frosting (from Step 5). Sprinkle the remaining chopped pecans (from Step 1) on top and finish each cupcake by placing a whole reserved pecan in the center. For an extra touch, I sometimes drizzle with a little maple syrup or a pinch of flaky salt.