- Preheat oven to 350°F and line two baking sheets with parchment paper. Whisk together flour, cocoa, and salt in a medium bowl.
- Beat butter and sugars in a large mixer bowl at medium speed until creamy; beat in vanilla. Reduce speed to low and gradually add flour mixture; beat just until incorporated. Slowly drizzle in heavy cream and mix on low until completely incorporated and dough comes together in large pieces.
- Roll dough into 1-inch balls and place two inches apart on prepared baking sheets. Use the back of a teaspoon to press down in the center of each ball to form a thumbprint. Gently press any large cracks back together, and chill thumbprints for 30 minutes in the refrigerator.
- Bake, rotating pans halfway through, for 12 to 13 minutes, until tops and edges are set. Let cookies cool for 10 minutes on baking sheets, then transfer to a wire rack to cool completely (if desired, use a round cookie cutter to round the cookies into perfect shape while they cool.
- Line two baking sheets with parchment paper. Combine Ghirardelli Milk Chocolate Thumbprint Drops and 60% bittersweet chocolate chips in a glass bowl. Microwave in 10-second bursts, stirring until melted and smooth. Stir in peppermint extract.
- Dip half of each cookie in melted chocolate, tapping gently to remove excess chocolate. Place dipped cookies on prepared baking sheets and chill in the refrigerator for 20 minutes to set chocolate.
- For the filling, beat butter, salt, vanilla, and peppermint extract in a mixer bowl until combined. Reduce speed to low and beat in powdered sugar until incorporated. Add heavy cream and mix on low speed until combined, then beat on medium speed for 1 minute, until light and airy.
- To assemble the cookies, transfer the filling to a piping bag fitted with a round tip. Pipe peppermint creme filling in the center of each thumbprint, and top with a Ghirardelli Milk Chocolate Thumbprint Drop.
Note - Freeze cookies: Once assembled, freeze cookies flat on a baking sheet for 1 hour. Once frozen, transfer to an airtight container or freezer bag and freeze up to 1 month. Thaw the cookies still covered (to avoid condensation from forming).
Recipe and Photo Credit: @tutti_dolci