Makes about 4 dozen cookies.
For filling
8 ounces cream cheese, at room temperature
1 cup powdered sugar
¼ cup flour
1½ teaspoons vanilla extract
1 cup chopped walnuts, optional
½ cup coconut
For cookies
2 ¼ cups flour
¼ teaspoon salt
1 cup (2 sticks) unsalted butter, at room temperature
1 cup powdered sugar
2 teaspoons vanilla extract
For frosting
1 cup milk chocolate or semisweet chocolate chips
4 tablespoons (½ stick) unsalted butter
2 tablespoons water
1 tablespoon white corn syrup
1½ cups powdered sugar
Directions
To prepare filling: In a bowl of an electric mixer on medium-high speed, beat cream cheese until creamy, about 1 minute. Gradually add powdered sugar and beat until light and fluffy, about 2 minutes. Add vanilla extract and beat until well-combined. Reduce speed to low, add flour and mix until just incorporated. Stir in nuts, if using, and coconut, and reserve.
To prepare cookies: Preheat oven to 350 degrees and line baking sheets with parchment paper.
In a medium bowl, whisk together flour and salt, and reserve.
In a bowl of an electric mixer on medium-high speed, beat butter until creamy, about 1 minute. Gradually add powdered sugar and beat until light and fluffy, about 2 minutes. Add vanilla extract and beat until well-combined. Reduce speed to low, add flour mixture and mix until just incorporated.
Shape teaspoonfuls of dough into balls, place 2 inches apart on prepared baking sheets and make an indentation in center of each cookie with your thumb. Bake until very lightly browned, 12 to 15 minutes. Remove from oven and cool 2 minutes before transferring cookies to a wire rack.
While cookies are still warm, fill indentations with cream cheese mixture. Cool cookies completely.
To prepare frosting: In a double boiler over gently simmering water (or in a microwave oven), melt chocolate chips and butter. Stir in water and corn syrup. Add powdered sugar and whisk until smooth. Frost each cookie.
2004 Finalist: Dianne Kemp of Chanhassen, Minnesota