Preheat an oven to 350f (180c) and prep a cupcake pan with liners.
Into a large mixing bowl, add the oil, sugar, eggs, vanilla extract, salt, and espresso powder, and mix with a whisk until well combined.
Sift the cocoa powder and mix until well combined.
Add the flour, baking powder, and baking soda and mix until almost combined.
Add the hot coffee and mix until the mixture is smooth and homogeneous.
Use an ice cream scoop to fill out the cupcake ⅔ full (do not overfill) and bake the cupcakes in a 180c (350f) preheated oven for about 20 minutes or until a toothpick comes out clean.
Cool the cupcakes for 10 minutes and transfer them to a cooling rack to cool completely.
Make the cherry filling
In a medium saucepan, combine the pitted cherries, lemon juice, and sugar. Heat over medium heat, stirring occasionally, until the cherries release their juices and the mixture starts to simmer.
In a small bowl, mix the cornstarch with water until smooth. This creates a slurry that will help thicken the cherry topping. Slowly pour the cornstarch mixture into the simmering cherries, stirring constantly.
Continue cooking for about 2-3 minutes, or until the mixture thickens to your desired consistency. Remove from the heat and add the Kirsch. Remember that it will thicken further as it cools.
Make a small hole in the middle of each cupcake. You can use a piping tip, a butter knife, or a cupcake corer. Fill each cupcake with the cooled cherry filling.
Transfer the whipped cream to a piping bag with a star tip and pipe the cupcakes with the cream.
For decoration, drizzle extra cherry filling juice on top of the whipped cream, and top it with a cherry.
Notes
Don’t skip the coffee in the chocolate cupcake, you can’t taste the coffee, it simply enhances the chocolate flavor.
Use room temperature ingredients. It is important that you use room-temperature ingredients like eggs. This step ensures that your mixture mixes into a homogenous mixture and bakes perfectly.
For the cherry filling, opt for fresh or frozen cherries over canned for a more authentic flavor.
Core the cooled cupcakes carefully, leaving a border around the edges to prevent filling leakage.
Don’t overmix the batter, you don’t want to develop the gluten in the flour. This step ensures you have moist cupcakes and not dense and dry cupcakes.
Measure your flour correctly! When measuring your flour, avoid scooping it with a measuring cup. Instead, stir the flour with a spoon to create as many air pockets as possible, and spoon it into your measuring cup. Finally, level it with a back of a knife.
Be patient! I know it's extremely tempting to eat and frost these cupcakes as soon as they come out of the oven, but let them cool for at least 30 minutes. This will make them firmer and prevent them from crumbling.
I suggest letting these cupcakes cool for 5 minutes before transferring them to a wire rack to cool for at least 20 more minutes. This step ensures that the frosting won't melt off the cupcakes.