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For these sweet, rich cookies, you'll use your thumb to create a well in the fresh chocolatey dough before baking, then fill each well with a duo of sour cherry spread and cream cheese frosting.
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Place an oven rack in the center of the oven; preheat to 350°F. Melt the butter in a large bowl in the microwave (or melt in a small pot on the stove, then transfer to a large bowl). Add the brown sugar, granulated sugar, and egg; whisk to thoroughly combine. In a separate bowl, whisk together the flour, cocoa powder, vanilla powder, 1/2 teaspoon of the baking powder (you will have extra), and a pinch of salt. Transfer the dry ingredients to the bowl of wet ingredients. Using a spatula, gently mix just until no streaks remain (be careful not to overmix).
Line a sheet pan with parchment paper. Scoop about 2 tablespoons of the dough into your hands; roll into a ball (if the dough is too sticky, wet your hands with water to prevent it from sticking), then place on the sheet pan. Repeat with the remaining dough to ensure the cookies are the same size, evenly spacing them out on the sheet pan. Using your thumb, press into the center of each ball to create a deep well. Bake 10 to 12 minutes, or until the dough is set and cooked through. Transfer to a cooling rack; let stand at least 10 minutes. (If the wells have risen too much during baking, using the bottom rounded side of a spoon, press into the center of the cookie to form a deep well.)
When cool enough to handle, evenly divide the sour cherry spread, followed by the cream cheese frosting, among the wells of the baked cookies. Enjoy!
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