Preheat oven to 350°F (177°C). Line a standard muffin tin with paper liners.
In a large bowl, whisk together the flour, cocoa powder, baking powder, baking soda, and salt until well combined and no lumps remain.
In the bowl of a stand mixer fitted with the paddle attachment, beat the Redpath® Dark Brown Sugar, canola oil, and sour cream on medium speed until well mixed; 3 minutes. Add the eggs one at a time, beating well after each addition. Mix in the vanilla extract.
Add the dry ingredients to the bowl. Mix on low speed until just combined. Slowly add the hot coffee into the batter with the mixer on low to medium-low speed. Mix until batter is smooth and coffee is completely incorporated; 1 minute.
With a trigger-style ice cream scoop or a ladle, fill the prepared muffin tin wells ⅔- to ¾-full.
Place tin into the preheated oven and bake for 15 to 20 minutes or until a skewer inserted into the centre comes out clean.
Let cupcakes cool in the tin for about 5 minutes before removing and cooling completely on a wire cooling rack.
Using a paring knife, cut a cone-shaped piece (1 inch deep and ¾ inch wide) out of the centre top of each completely cooled cupcake (see Chef’s Tips). With a spoon, fill the cavity with the cooled cherry filling; ensure there is at least one cherry in the cavity.