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In a large mixing bowl cream butter and sugar.
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Separate egg, reserve white for later use add yolk to creamed mixture.
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Add milk and vanilla to creamed mixture, mixing well after each addition.
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In a separate bowl combine dry ingredients and whisk to combine.
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Combine creamed and dry mixtures with electric mixer; beat until well combined.
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Wrap dough in plastic wrap and chill for 2 hours or until dough is easy to work with.
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Preheat oven to 350°F.
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In a small sauce pan melt caramels into whipping cream over low heat.
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Stir until mixture is smooth; set aside.
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Slightly beat reserved egg white.
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Shape dough into 1-inch balls.
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Roll balls in egg white then in pecans.
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Place balls one inch apart on cookie sheet sprayed with vegetable oil spray.
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Using your thumb, make an indentation in each cookie.
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Bake for 10 minutes or until edges of cookies are firm.
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Spoon caramel into indentation.
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Move cookies to wire racks to cool.
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Melt chocolate chips and shortening; cool mixture slightly then place in a zip top bag.
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When all cookies have been filled, clip tiny corner off of bag and drizzle chocolate over cookies.
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Let cookies stand until chocolate and caramel are set.
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Prep time does not include chilling time.