Line an 8-inch square pan with aluminum foil, with some extra for lifting out of the pan, and set aside.
In a microwave-safe bowl, combine the caramels, milk chocolate chips, and heavy cream. Microwave, uncovered, on high for 60 seconds, then stir. Microwave 60 seconds longer, stirring every 15 - 20 seconds, until the caramels and chocolate chips are melted and the mixture is smooth.
26 caramels, unwrapped, 1 cup milk chocolate chips, ¼ cup heavy whipping cream
Evenly spread the mixture into the foil-lined pan. Refrigerate until firm, at least 1 hour.
Using the foil, lift the candy out of the pan. Using a sharp knife, cut into 2" squares. Roll each square into a ball. Refrigerate until ready to dip.
In a microwave-safe bowl, melt the semi-sweet chocolate chips and vegetable shortening, stirring until smooth. Dip each caramel ball into the chocolate, allowing the excess to drip off. Place on a wax paper-lined baking sheet. Sprinkle with a pinch of flaked sea salt. Refrigerate until firm. Store in the refrigerator, but allow to sit at room temperature for about 15 minutes before serving. The coating will soften when it warms up.
1⅓ cups semi-sweet chocolate chips, 1 tablespoon vegetable shortening