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Preheat oven to 350°F. Line baking sheets with parchment paper; set aside. In a large bowl, combine flour and sugar. Using a pastry blender, cut in butter and vanilla until mixture resembles fine crumbs and starts to cling. Form the mixture into a ball, kneading until smooth.
Shape dough into 1-inch balls. Place the balls 2 inches apart on the prepared pans. Using your thumb, make an indentation in each dough ball. Bake for 12 to 14 minutes or until edges are light brown. If cookie centers puff during baking, re-press centers with the rounded side of a measuring teaspoon. Cool on pans for 5 minutes. Transfer to a wire rack; cool completely.
In a small heavy saucepan, combine caramels and whipping cream. Cook and stir over very low heat until caramels melt and the mixture is smooth. Spoon a scant teaspoon into each thumbprint indentation.
If desired, before sprinkling on salt, top caramel with chocolate drizzle: In a small saucepan, heat and stir bittersweet chocolate and shortening until chocolate melts and is smooth. Spoon over cooled cookies.
Sprinkle each cookie with several grains of salt.