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Fudge Filled Chocolate Crinkle Cookies

Chocolate crinkle cookies with a smooth fudge filling that stays soft at room temperature
Course Dessert
Servings 15 cookies

Ingredients
  

Fudge Filling

  • ¾ cup (4 1/2 ounces) semisweet chocolate chips
  • ½ cup (6 ounces) sweetened condensed milk

Chocolate Crinkle Cookies

  • 1 ⅓ cups (6 ounces) all purpose flour, sifted
  • 2 tablespoons unsweetened cocoa powder, preferably Dutch process
  • 1 ½ teaspoons baking powder
  • ½ teaspoon fine sea salt
  • cup (2 5/8 ounces) unsalted butter, softened
  • 2 ½ cups (9 5/8 ounces) powdered sugar, sifted and divided
  • 2 large eggs
  • 1 teaspoon pure vanilla extract
  • 2 ounces unsweetened chocolate, melted and cooled to room temperature

Instructions
 

Fudge Filling

  • In a double boiler or in the microwave*, melt chocolate chips and sweetened condensed milk together until smooth. Set aside to cool while preparing cookie dough.
  • Cover and refrigerate for two hours. Roll filling into 1-inch balls.

Chocolate Crinkle Cookies

  • In a medium bowl, whisk together flour, cocoa powder, baking powder and salt.
  • In a large bowl, beat butter with an electric mixer until light and fluffy.
  • Gradually beat in 2 cups (7 3/4 ounces) of powdered sugar until well combined. Set aside remaining 1/2 cup powdered sugar in a shallow dish.
  • Beat in eggs and vanilla in three separate additions, until smooth. Stop to scrape bowl as needed.
  • Beat in melted chocolate until combined. Beat in flour mixture just until combined.
  • Cover and refrigerate dough for 2 hours. Don't skip this step.
  • Preheat oven to 350ºF. Line two large baking sheets with parchment paper.
  • Roll dough into 15 2-inch balls, 1 1/4 ounce each. Flatten each ball into a 3-inch disk. Place a fudge ball in the center of each disk and wrap dough around it, pinching edges together to seal. Roll dough balls generously in remaining powdered sugar.
  • Place dough balls three inches apart on prepared baking sheets. Bake until cookies puff up and tops are set, about 11-13 minutes. Transfer cookies to a cooling rack.

Notes

*To melt fudge filling in microwave, heat for 30 seconds. Stir, then microwave for 10 second intervals, stirring until melted.
MAKE AHEAD INSTRUCTIONS: To make cookie dough one day ahead, prepare cookie dough. Cover the surface with plastic wrap and refrigerate in a covered container up to 24 hours. To make fudge filling one day ahead, prepare filling and chill for 1 1/2 to 2 hours. Roll filling into 1-inch balls and place on a parchment lined tray. Cover tightly with plastic wrap and refrigerate up to 24 hours. 
Keyword chocolate, cookies