Preheat oven to 350°F. Line two baking sheets with parchment paper, set aside.
In a medium bowl, whisk together the flour, cocoa, salt and baking powder. Set aside.
In the bowl of a stand mixer, fitted with the paddle attachment, mix the butter and sugar until light and fluffy, about 2 minutes. Add the egg yolks and vanilla and mix until combined. Gradually add the flour mixture to the butter mixture, beating until combined.
Shape the dough into 1-inch balls and coat in the granulated sugar. Place onto the prepared baking sheets, about 2 inches apart. Use a ¼ teaspoon measuring spoon to gently make an indentation in the center of each ball. Bake until the cookies feel set, about 9 to 11 minutes.
Remove pans from the oven, and press down centers again. Allow to cool on the pans for 10 minutes before transferring to a wire rack to cool completely.
To make the topping, beat the heavy cream with the sugar and vanilla until soft peaks form. Transfer to a piping bag, fitted with a small star tip.
Fill the center of each cooled cookie with a cherry and some of the syrup. Pipe a ring of whipped cream around each cherry and top with chocolate sprinkles. Serve immediately or store in the fridge in an airtight container until ready to eat.