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Preheat the oven to 350 degrees F. Line 2 regular 12-cup cupcake tins with paper liners.
In a large bowl, combine the flour, cocoa powder, sugar, baking soda, baking powder, and salt. Whisk until well blended.
In a medium bowl, whisk together the milk, malted milk powder, and espresso powder. Add the canola oil and eggs; whisk to blend. Add the milk mixture to the flour mixture and beat until smooth. Add the sour cream and vanilla and beat until well combined. Stir in the miniature chocolate chips.
Divide the batter among the prepared cupcake tins, filling only halfway full. Bake the cupcakes for 15 to 17 minutes, until they spring back when touched and a toothpick inserted into the center emerges clean.
While the cupcakes bake, prepare the buttercream. In the bowl of an electric mixer fitted with the paddle attachment, mix together the sugar and the butter on medium-low speed until well blended. Add the vanilla and whipping cream and beat on medium speed for 2 minutes, until light, spreadable and fluffy. Beat in the cherry preserves until well incorporated.
When the cupcakes have finished baking, let sit in the pans for 2 minutes and then transfer the cupcakes to wire racks to cool for 10 minutes more.
While the cupcakes cool, transfer the buttercream to a pastry bag fitted with a large star tip. Alternatively, you can frost the cupcakes with a knife or offset spatula. When the cupcakes have cooled, pipe the buttercream in decorative swirls on top of the cupcake (or swirl with a spatula). Garnish the top of each cupcake with a malted milk ball or cherry and serve.
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