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

In a large bowl, beat the softened butter and powdered sugar together until light and fluffy. Add the vanilla extract and mix until incorporated.

Gradually add the flour and salt, mixing until a dough forms.

Roll the dough into 1-inch balls and place them on the prepared baking sheets, spacing them about 2 inches apart.

Press each cookie dough ball down slightly with the back of a spoon or your fingers to form a flat disk.

Bake for 12-15 minutes, or until the edges of the cookies are lightly golden. Remove from the oven and let them cool on the baking sheets for a few minutes before transferring to wire racks to cool completely.

While the cookies cool, melt the caramels and evaporated milk (or cream) in a saucepan over low heat, stirring occasionally until smooth.

Once the cookies are completely cooled, spoon a small amount of caramel onto each cookie and spread it evenly.

In a microwave-safe bowl, melt the milk chocolate chips and shortening in 30-second intervals, stirring between each, until smooth.

Drizzle the melted chocolate over the caramel-covered cookies or dip the cookies into the chocolate for a more decadent finish.

Allow the chocolate to set before serving or storing.