Start by making the Coconut Caramel Sauce. Whisk together the coconut milk, vanilla, and salt in a small bowl. Set aside. Combine the brown sugar and water in a small saucepan over medium-high heat. Bring the mixture to a boil. Once it begins to boil watch closely and whisk until the mixture starts to smell like caramel and turn a golden color, and then to a light brown. This will take about 5-6 minutes. When you see that it has started to turn brown, slowly pour in the coconut milk mixture, whisking constantly and quickly. The sugar will harden around the whisk, don’t worry, it will melt. Just keep whisking! Continue to heat over medium-high until mixture has thickened and is a light caramel color, about 5 minutes more (dont let it get too thick, it will thicken as it sits). Remove from the heat and set aside.
Preheat oven to 350 degrees.
In the bowl of a stand mixer or large mixing bowl combine the flour, cocoa powder, baking soda, salt and suger. Whisk to combine. In a small bowl add the coconut milk, egg, canola oil and vanilla extract. Stir lightly and then add to the flour mixture. Beat until the ingredients are well combined and then add the warm coffee. Beat well, until the mixture is very smooth. Fold in chocolate chips. Line a muffin tin with liners and using a 1/4 cup measure, add batter to each cup. Bake for 15-18 minutes. Let cool completely before filling and frosting.
While the cupcakes bake make the frosting. Cream the butter in the bowl of an electric mixture until completely smooth and creamy. With the mixer on low speed, add in powdered sugar slowly. Gradually increase mixer speed and add vanilla. Then beat for 2-3 minutes, scraping down sides and bottom of the bowl. Beat in the coconut milk. Continue to whip for another 4-5 minutes, continuously scrapping. If frosting is too thick, add coconut milk 1 teaspoon at a time until desired consistency is reached. If it’s too thin, add powdered sugar gradually until it thickens (I like to keep mine very thin and less sugary). Fold in shredded coconut and toasted coconut and mix until just combined.
To assemble the cupcakes: Use a small paring knife to cut a cone-shaped piece from the center of each cupcake. Fill the hole with coconut caramel sauce, then replace the top portion of the cone (you'll need to slice off the tip). Transfer the Vanilla Coconut Frosting to a pastry bag fitted with a tip. Pipe frosting into a swirl on each cupcake (you can also just spread the frosting on with a knife). Sprinkle with toasted coconut and drizzle with additional coconut caramel sauce over the top, if desired.