Deep Chocolate Chippy Tiramisu Sandwich Cookies
Prep time: 
Cook time: 
Total time: 
Yield: About 20 sandwich cookies
 
Cookie part adapted from Epicurious
ingredients:
Cookies
  • 1 cup all purpose flour
  • 3 tablespoons unsweetened cocoa powder
  • 1 teaspoon baking soda
  • ½ teaspoon salt
  • ½ cup (1 stick) unsalted butter, room temperature
  • ⅔ cup (packed) golden brown sugar
  • ¼ cup sugar
  • 1 large egg
  • 2 teaspoons water
  • 1 teaspoon vanilla extract
  • 1 to 2 teaspoon(s) instant coffee or espresso powder *
  • 1 cup mini semisweet chocolate chips
Topping
  • ⅓ cup powdered sugar
  • 1 teaspoon unsweetened cocoa powder
Mascarpone Filling
  • 4 oz. mascarpone cheese, at room temperature
  • 3 oz. cream cheese, at room temperature
  • ⅓ cup sugar
  • 2 teaspoons instant coffee or espresso powder *
  • 2 teaspoons coffee liqueur (you can use 1 tablespoon strong coffee or espresso if you don't want to use liqueur)
Chocolate Filling
  • ⅓ cup confectioners (powdered) sugar (plus more to thicken as needed)
  • 1 tablespoon unsweetened cocoa powder
  • 2 teaspoons instant coffee or espresso powder *
  • 1 to 2 tablespoons cool coffee or espresso (or just enough to wet the filling so it's spreadable)
  • 1 tablespoon coffee liqueur (optional) **
directions:
Make the Cookies
  1. Combine the sugar and cocoa topping in a small bowl. Set aside.
  2. Preheat oven to 325°F. Line 2 baking sheets with parchment paper. Sift flour, cocoa, baking soda, and salt into bowl. Using electric mixer, beat butter and both sugars in bowl until well blended. Add egg, 2 teaspoons water, vanilla, and instant coffee; blend well. Beat in flour mixture. Stir in mini chocolate chips. Drop dough by tablespoonfuls onto prepared sheets, spacing 2 inches apart. Sprinkle each dough ball with a bit of the sugar-cocoa topping. Bake until tops are just firm to touch and no longer shiny, about 13 minutes. Cool cookies on sheets 10 minutes. Transfer to racks and cool.
Make the Mascarpone Filling
  1. In a stand mixer bowl or a bowl using electric beaters, beat together the mascarpone cheese and cream cheese, about 3 minutes. Add sugar and coffee liqueur, and beat for an additional 2 to 3 minutes.
Make the Chocolate Filling
  1. Mix all the ingredients together in a small bowl, adding powdered sugar, if needed, to get it to a consistency where it will spread, but it's not too stiff.
Assemble the cookies
  1. Place all of the cookie flat side up on work surface. Spread half the cookies with 1 tablespoon of the mascarpone filling and the the other half of the cookies with about 1 teaspoon chocolate filling. Sandwich the chocolate spread cookies with the mascarpone spread cookies. Arrange on platter; cover and chill at least 2 hours. (Can be made 2 days ahead. Keep chilled).
  2. Store covered in the fridge IF there's any left!
notes:
* If you prefer a stronger coffee flavor, add more. Less, add less. Taste both fillings and adjust the coffee flavor and/or liqueur, to your liking.
** If you want more liqueur in the chocolate filling, by all means add it. Just compensate with more powdered sugar and/or cocoa so it remains thick and spreadable; not soupy.
Recipe by parsley sage sweet at https://www.parsleysagesweet.com/2009/12/23/one-no-two-macarons-december-cookie-baking-and-my-fear-of-the-tripod/