Step 1: Preheat your oven to 350°F (175°C). Grease and flour two 8-inch round cake pans, or line them with parchment paper.
Step 2: In a large bowl, whisk together the all-purpose flour, cocoa powder, baking soda, baking powder, salt, and granulated sugar. Set aside.
Step 3: In a separate medium bowl, whisk together the vegetable oil, eggs, milk, and 2 teaspoons vanilla extract.
Step 4: Pour the wet ingredients into the dry ingredients and mix on low speed (or by hand) until just combined. Gradually add the boiling water, mixing until the batter is smooth. Be careful not to overmix.
Step 5: Divide the batter evenly between the two prepared cake pans. Bake for 30-35 minutes, or until a wooden skewer inserted into the center comes out clean. Let the cakes cool in the pans for 10 minutes, then invert onto a wire rack to cool completely.
Step 6: While the cakes cool, prepare the Coconut-Almond Filling. In a medium bowl, combine the 14 oz can of sweetened shredded coconut, sweetened condensed milk, and ½ teaspoon almond extract. Stir until thoroughly combined. Gently fold in the ¾ cup toasted, chopped almonds. Cover and chill in the refrigerator to firm up slightly.
Step 7: Once the cakes are completely cool, use the handle of a wooden spoon or a skewer to poke holes evenly across the top of each cake layer, about 1 inch apart. Warm the 13.5 oz can of full-fat coconut milk until just steaming (do not boil). Slowly pour the warm coconut milk over both cake layers, ensuring it soaks into the holes. Let the cakes rest for at least 20 minutes to absorb the liquid.
Step 8: Prepare the Coconut Frosting. Chill a large mixing bowl and beaters in the freezer for 10-15 minutes. Pour the 1¾ cups heavy whipping cream and 1 teaspoon vanilla extract into the cold bowl. Beat on medium-high speed until soft peaks form. Gradually add the powdered sugar and continue beating until stiff peaks form. Gently fold in the ½ cup sweetened shredded coconut.
Step 9: Prepare the Chocolate Ganache Drip. In a heatproof bowl, combine the chopped semisweet/bittersweet chocolate, 1 cup heavy cream, and cubed unsalted butter. Heat the cream until it simmers, then pour it over the chocolate mixture. Let stand for 2 minutes, then stir gently from the center outwards until smooth and glossy. Let the ganache cool to a pourable consistency (about body temperature).
Step 10: To assemble, place one soaked cake layer on your serving plate or cake stand. Spread half of the chilled coconut-almond filling evenly over the top. Place the second cake layer on top and spread the remaining half of the coconut-almond filling.
Step 11: Frost the top and sides of the entire cake with the coconut frosting, creating a smooth layer. Use a spoon or a squeeze bottle to carefully apply the cooled ganache around the edge of the cake, allowing it to drip naturally down the sides. Pour any remaining ganache over the top of the cake and spread evenly.
Step 12: Garnish the cake with additional toasted almond slices, flaked coconut, and chocolate shavings, if desired. Chill the cake for at least 1 hour before slicing and serving to allow the frosting and ganache to set.