Preheat oven to 350°F. Line two 12-count cupcake pans with 16 cupcake liners and set aside.

In a large mixing bowl, sift together the flour, cocoa powder, baking powder, baking soda, and salt. Whisk in the granulated sugar and brown sugar until well combined. Add in the oil, egg, vanilla extract, and buttermilk and mix until just combined.

Add the instant espresso powder into the boiling water and mix until dissolved, then add to the mixing bowl. Mix with the rest of the ingredients until well combined, making sure not to over mix the batter. The batter will be thin, this is okay.

Evenly distribute the batter between all 16 cupcakes liners, making sure to only fill them a little over half way full. Bake at 350°F for 18-20 minutes or until a wooden toothpick inserted into the cupcakes comes out clean. Remove from the oven and carefully remove the cupcakes from the pan. Transfer the cupcakes to a wire rack to cool.

Add the cherries, granulated sugar, lemon juice, water, and corn starch to a saucepan and mix until well combined. Heat over medium heat, stirring often, until the mixture has thickened. Remove from the heat and stir in the vanilla extract, then set aside to cool.

Pour the water in a small bowl and sprinkle the unflavored gelatin on top. Allow to sit for a few minutes. Transfer to the microwave and microwave for a few seconds until the gelatin has dissolved. Stir well and set aside to cool for a few minutes.

In the bowl of a stand mixer fitted with the whisk attachment, or in a large mixing bowl using a hand-held mixer, add the heavy whipped cream, powdered sugar, and vanilla and mix on medium speed until it starts to thicken. Turn the mixer to low, slowly pour in the gelatin, then continue mixing at medium-high speed until stiff peaks form.

Once the cupcakes and cherry filling have cooled, use a knife to cut out a hole in the center of each cupcake. Scoop about 1-1.5 tablespoons of the cherry filling into each cupcake. Then pipe the whipped cream on top. Garnish with chocolate shavings and a cherry on top!