Preheat oven to 350°F. Line cupcake tins with paper liners.
In a large bowl, sift together the flour, sugar, baking soda and cocoa powder.
In a separate bowl, whisk together the butter, oil, buttermilk, eggs, extract and cherry juice until well combined.
Add the wet ingredients to the dry ingredients and whisk until it has all been incorporated. Slowly add in the boiling water, whisking well until the batter is shiny and smooth. Fold in the chopped cherries and chocolate chunks.
Fill the cupcake tins 2/3 full with the batter. Bake for 22-25 minutes, until a toothpick inserted comes out clean. Remove from oven and allow to cool slightly before removing from the pan and placing on a cooling rack.
While your cupcakes are cooling, beat the butter in the bowl of an electric mixer fitted with the paddle attachment until it is light and fluffy. Slowly add the powdered sugar about 1 cup at a time, scraping the sides down in between additions. When all of the sugar has been incorporated and the frosting is light and fluffy, add in the cherry juice and mix until combined.
Top cooled cupcakes with frosting, garnish with cherry and serve.