Let cookie dough stand at room temperature 10 minutes to soften. Heat oven to 350°F.
In large bowl, mix cocoa, whipping cream and 1/2 teaspoon salt with wooden spoon until well blended. Crumble cookie dough into cocoa mixture; add chocolate chips, and stir until well blended. Place dough in freezer 15 minutes for easier handling.
Using measuring tablespoon or small ice cream scoop, shape dough into 30 balls. Freeze 15 minutes. Place 1 caramel inside each dough ball, covering completely and reshaping ball around caramel. Dough will be sticky; wet hands slightly if helpful. Place balls 2 inches apart on ungreased cookie sheets.
Bake 9 to 13 minutes or until edges of cookies are set. Cool on cookie sheets 2 minutes; remove to cooling racks. Cool completely, about 20 minutes.
Meanwhile, in small microwave bowl, microwave 20 caramels and 2 tablespoons whipping cream uncovered on High 45 seconds to 1 minute 15 seconds, stirring every 15 seconds or until caramel is melted and mixture is smooth.
Spoon or drizzle caramel over cookies. Just before serving, sprinkle with salt.