1. Preheat oven to 350. Line cookie sheets with parchment paper; set aside. In large bowl combine flour and sugar. Using pastry blender, cut in butter and vanilla until mixture resembles fine crumbs and starts to cling. Form mixture into a ball, kneading until smooth.
2. Shape dough into 1-inch balls. Place balls 2 inches apart on prepared cookie sheets. Using your thumb, make indentation in each dough ball. Bake for 12 to 14 minutes or until edges are lightly browned. If cookie centers puff during baking, re-press centers with the rounded side of a measuring teaspoon. Cool on cookie sheets for 5 minutes. Transfer to a wire rack; cool completely.
3. In a small heavy saucepan combine caramels and whipping cream. Cook and stir over very low heat until caramels are melted and smooth. In a separate small sauce pan, heat and stir chocolate pieces and 1/2 teaspoon of shortening or butter until chocolate is melted and smooth.
4. Spoon a scant teaspoon caramel mixture into each thumbprint. Drizzle chocolate over caramel mixture . Sprinkle cookie with several grains of salt.
Makes 32 cookies
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