In a large bowl using an electric hand mixer or a stand mixer fitted with a paddle attachment, beat the softened butter and powdered sugar on medium speed until light and fluffy, about 2-3 minutes.

Beat in the vanilla extract. In a separate medium bowl, whisk together the all-purpose flour and salt. With the mixer on low speed, gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.

Cover the dough and chill in the refrigerator for at least 30 minutes. This will make it easier to handle and prevent the cookies from spreading too much.

Preheat your oven to 350°F (175°C). Line two large baking sheets with parchment paper.

Scoop the chilled dough and roll it into 1-inch balls (about 1 tablespoon each). Place the balls about 2 inches apart on the prepared baking sheets.

Using your thumb or the back of a 1/2 teaspoon measuring spoon, gently press an indentation into the center of each dough ball.

Bake for 12-14 minutes, or until the edges are lightly golden. The centers will still be pale.

Remove the cookies from the oven. If the indentations have puffed up, gently re-press them with the back of the measuring spoon while they are still warm. Let the cookies cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.

While the cookies cool, prepare the caramel filling. In a small, heavy-bottomed saucepan, combine the unwrapped caramels and heavy cream. Heat over low heat, stirring constantly, until the caramels are completely melted and the mixture is smooth.

Carefully spoon the warm caramel into the indentation of each cooled cookie. Let the cookies sit for about 15-20 minutes, or until the caramel is set.

Once the caramel is set, melt the chocolate. Place the milk chocolate chips and optional coconut oil in a microwave-safe bowl. Microwave in 20-second intervals, stirring in between, until completely melted and smooth.

Using a spoon or a piping bag, drizzle the melted chocolate over the cookies. Allow the chocolate to set completely at room temperature (about 1 hour) or in the refrigerator (about 15 minutes) before serving.