Chocolate Peppermint Thumbprints

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Chocolate Peppermint Thumbprints

This festive take on a classic thumbprint cookie features a buttery red and white marbled shortbread, dark chocolate filling with a hint of peppermint, and crunchy candy cane bits sprinkled on top.

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Ingredients

For Cookies:

  • ½ ½ cup (1 stick) unsalted butter at room temperature
  • ⅓ cup granulated sugar
  • ½ ½ teaspoon vanilla extract
  • ¼ ¼ teaspoon almond extract
  • 1 ⅛ 1 ⅛ cup all-purpose flour that's a generously measured cup or 1 cup + 2 tablespoons
  • 1½ tablespoons cornstarch
  • ¼ ¼ teaspoon kosher salt
  • Red food coloring

For Chocolate Filling:

  • 3½ ounces dark or semisweet chocolate finely chopped
  • ½ ½ tablespoon butter
  • ½ ½ tablespoon corn syrup
  • ½ ½ teaspoon oil-based peppermint extract more or less to taste
  • candy cane crunch or crushed candy canes for topping
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Instructions

  1. Preheat oven to 375 degrees F. Line a light-colored aluminum cookie sheet with parchment paper. If using non-stick cookie sheets with a coating or darker finish, I recommend stacking two cookie sheets on top of one another to provide some extra insulation against browning.
  2. In a large mixing bowl or the bowl of a stand mixer, beat butter and sugar together until fluffy, 1 to 2 minutes. Mix in extracts.
  3. Add dry ingredients and mix on low speed until incorporated. The dough may appear crumbly at first, keep mixing or give it a knead to bring it together into a soft dough.
  4. Remove approximately half the dough from the bowl. To remaining dough, add red food coloring and mix until color is evenly distributed.
  5. Use a small cookie scoop to divide both colors of dough into 1-inch balls. Split balls in half, combining half a red ball with half a white one to create a swirled effect. Roll into a smooth ball and arrange on prepared baking sheet, leaving 2 inches of space between balls.
  6. Gently flatten the dough balls slightly with the ball of your hand. Make an indentation into each cookie using your thumb or the back of a rounded 1/2 teaspoon (something like a melon baller, or even a marble would also work well). Don’t press down far enough for the dough to crack; you just need an indentation about half the depth of the cookie to start with. Place entire baking sheet in freezer for 10 minutes.
  7. Bake for 10 to 12 minutes or until cookies are puffed and bottoms are just barely starting to brown. Remove from oven, and while the cookies are still warm, use the same measuring spoon to re-form the thumbprint. Let cool for 10 minutes before transferring to a wire rack to cool completely.
  8. To make filling, gently melt chocolate together with butter and corn syrup in a double boiler, a saucepan over the lowest heat setting possible, or in the microwave on 50% power in 30 second intervals. Stir in peppermint extract.
  9. Spoon or pipe filling into the thumbprints, then sprinkle with crushed candy canes. Let sit at cool room temperature or refrigerate briefly until chocolate is set.
  10. Cookies will keep in an airtight container for up to 5 days.
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