Preheat the oven to 350 degrees Fahrenheit. Line a cupcake pan with 12 parchment baking cups. Adjust the oven rack to the middle position.
Pulse the raw cashews in a food processor or high-speed blender, a few seconds at a time, until they resemble a coarse flour. You don’t want any visible chunks of cashews. This should take about 1 minute. Be sure not to turn the cashew flour into cashew butter. Watch the texture closely.
Add the rest of the dry ingredients into the processor and pulse until well combined. In a medium bowl, mix all of the wet ingredients together. Add the dry ingredients into the wet. Stir just until combined and be careful not to over-mix (I just used a fork and spent a few minutes carefully mixing until no streaks remained.)
Divide the batter evenly among the 12 parchment-lined cups. This should leave you with each about 3/4 full. Bake for 16-20 minutes, until a toothpick inserted in the middle of a cupcake comes out clean. Set aside and transfer to a wire rack to cool off & begin preparing the chocolate buttercream.
Gently heat up the chocolate: in a microwave on medium power (about 60-120 seconds, stopping and stirring every 30 seconds) or on the stove top using a double boiler method on medium-low until melted. Set aside to slightly cool.
Scoop the coconut cream out of the can(s) of coconut milk into a medium mixing bowl. If you are using heavy cream, place it directly into the mixing bowl. Beat with an electric mixer on high speed until stiff peaks form (usually 2-3 minutes.) Cover and refrigerate the cream.
In the bowl of a stand mixer, beat the softened butter on medium speed for 1 minute.
Add in the coconut sugar and continue beating until light and fluffy, about 3-5 minutes. Be sure to scrape down the sides every minute or so. Pour in the cooled chocolate to the mixture and beat until well incorporated.
Add 2 out of 3 of the eggs and beat on medium speed for about 3 minutes. Add in the last egg and beat for another 3 minutes until the mixture is smooth.
Fold the chilled coconut/heavy cream into the chocolate filling until no there are no visible white streaks left, and stir in the vanilla extract. Pipe cupcakes with buttercream or spread on top using an offset spatula.