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In a large bowl, cream butter and confectioners' sugar until light and fluffy, 3-4 minutes. Beat in milk and vanilla. Combine flour and salt; gradually add to creamed mixture. Cover and refrigerate for 1 hour or until easy to handle.
On a lightly floured surface, roll out the dough to ¼-in. thickness. Cut into 2x1-in. strips. Place 1 in. apart on greased baking sheets.
Bake at 325° for 12-14 minutes or until lightly browned. Remove to wire racks to cool completely.
For filling, combine the caramels and milk in a large saucepan. Cook and stir over medium-low heat until caramels are melted and smooth. Remove from the heat; stir in the butter, sugar and pecans. Cool for 5 minutes. Spread 1 teaspoon over each cookie.
For icing, in a microwave-safe bowl, melt chips and milk; stir until smooth. Stir in the butter, confectioners' sugar and vanilla until smooth. Cool for 5 minutes.
Spread 1 teaspoon icing on each cookie; top each with a pecan half. Let stand until set. Store in an airtight container.