Step 1: Prepare the Cupcakes - Preheat your oven to 350°F (175°C). Line a muffin tin with cupcake liners.
Step 2: Melt the Chocolate - In a double boiler or microwave, melt 1/2 cup of the chopped semi-sweet chocolate with 1 tablespoon of canola oil until smooth. Stir occasionally to avoid burning. Set aside to cool slightly.
Step 3: Mix the Batter - In a large mixing bowl, whisk together the cooled chocolate mixture, remaining oil, and 4 tablespoons of melted butter until well combined. Add in the brown sugar, salt, and vanilla, mixing until smooth. Gradually add in the dry ingredients (flour, baking powder, and baking soda) until just combined.
Step 4: Bake the Cupcakes - Scoop the batter into the prepared cupcake liners, filling each about 2/3 full. Bake for 18-20 minutes, or until a toothpick inserted in the center comes out clean. Allow the cupcakes to cool completely in the pan before transferring them to a wire rack.
Step 5: Make the Frosting - In a medium saucepan, combine the remaining chopped chocolate, heavy cream, and brown sugar. Heat over medium heat, stirring until the chocolate is melted and the mixture is smooth. Remove from heat and stir in the salt and vanilla. Let it cool slightly.
Step 6: Toast the Coconut - While the frosting is cooling, spread the shredded coconut on a baking sheet and toast in the oven for about 5-7 minutes, stirring occasionally, until golden brown. Keep a close eye on it as it can burn quickly!
Step 7: Assemble the Cupcakes - Once the cupcakes are completely cooled, use a spatula or piping bag to frost each cupcake generously with the chocolate frosting. Top with a sprinkle of toasted coconut, and drizzle with melted chocolate for that signature Samoa look.
Step 8: Enjoy! - Allow the drizzled chocolate to set for a few minutes, then serve and enjoy your delicious Samoa Cupcakes!