Preheat the oven to 350 degrees F (175 degrees C). Line a 12-cup muffin tin with paper liners.
Sift flour, cocoa powder, and baking powder together in a bowl. Whisk sugar, milk, oil, eggs, and vanilla extract together in another bowl. Gradually add flour mixture to sugar mixture, whisking until combined. Spoon batter into the prepared muffin cups, filling each 2/3 full.
Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, 12 to 15 minutes. Allow to cool in the tin for 5 to 10 minutes. Transfer to a cooling rack to cool completely.
Place raspberry preserves into a pastry bag fitted with a round tip. Insert the tip into each cupcake and squeeze about 1 tablespoon of filling into the center of each.
Beat powdered sugar and butter for frosting together using a hand-held electric mixer until creamy and smooth. Beat in vanilla extract. If frosting seems too dry, add milk to reach desired consistency. Frost cooled, filled cupcakes.
This batter will be very runny, but they turn out just fine! Don’t be scared if the batter is a little soupy!
You can also fill the cupcakes by removing a small area from the center of the cupcake, filling with raspberry preserves, and placing the cap back in the center when done.
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