Beat the softened butter and powdered sugar until creamy, about 2 minutes.
Mix in the vanilla extract.
Add the flour and salt, mixing on low speed until a soft dough forms.
Shape the dough into a disc, wrap, and refrigerate for 30 minutes.
Preheat the oven to 350°F (175°C) and line baking sheets with parchment paper.
Scoop the dough into 1-tablespoon portions, roll into balls, and flatten slightly.
Place the cookies about 2 inches apart and bake for 10–12 minutes, until the edges are set and the bottoms are lightly golden.
Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
Melt the caramel candies with 2 tablespoons of heavy cream over low heat, stirring until smooth. Add more cream if needed.
Spread a small amount of caramel over each cooled cookie and chill for 10–15 minutes.
Melt the chocolate chips in short microwave intervals, stirring until smooth. Add the optional oil if needed.
Spread or drizzle chocolate over the caramel layer.
Add Christmas sprinkles while the chocolate is still soft.
Refrigerate for 15–20 minutes, until the chocolate sets.