Preheat the oven to 350 degrees F and line 12 muffin cups in paper liners. 

In a large bowl, whisk together the milk, vegetable oil, eggs, and vanilla.

Next, add the sugar and whisk to combine. 

Add the flour, cocoa, and baking powder. Whisk just until no large lumps remain– you don’t want to overmix! 

Divide the batter between the cupcake tins, filling each one ¾ of the way full. 

Bake for 16-18 minutes or until a toothpick inserted into the center comes out clean. Remove the cupcakes to a wire rack and cool completely before icing. 

Add the cherries and sugar to a small saucepan set over medium heat. Bring the cherry mixture to a bubble (not a rapid boil) and cook for 5-7 minutes or until the cherries have released their juices. 

In a small bowl, stir together the cornstarch and lemon juice. Add the slurry to the cherry mixture and cook it for an additional 2-3 minutes, or until the jam has thickened enough to coat the back of a spoon. 

Remove the jam from the heat and cool completely before using. 

Add the softened butter and melted chocolate to the bowl of a stand mixer fitted with the paddle attachment. Beat on medium speed until well combined– about 1 minute. 

With the mixer on low speed, slowly add the powdered sugar. Once all of the powdered sugar has been incorporated, add the vanilla extract. 

Scrape down the sides of the bowl and then turn the mixer to medium-high speed and beat until the buttercream becomes light and fluffy– about 1 minute. 

Transfer to a piping bag fitted with your choice of tip. 

To assemble, scoop a small hole (about 1 inch) out of the center of each cupcake and fill it with 1-2 teaspoons of cherry jam. Place the removed portion of the cupcake back on top of the jam and pipe the frosting on top. 

Garnish with fresh cherry, if desired. 

Store any leftover cupcakes in an airtight container in the fridge for up to two days.