Preheat the oven to 350°F and line a baking sheet with parchment paper. Set aside.
In a stand mixer fitted with a paddle attachment, cream together the butter and sugar until light and fluffy.
½ cup salted butter, ½ cup powdered sugar
Add the vanilla, baking powder, and flour and mix until well combined.
1 teaspoon vanilla extract, ½ teaspoon baking powder, 1 cup all-purpose flour
Shape the cookie dough into a large disc and wrap it with plastic wrap and refrigerate for 1 hour.
Sprinkle some flour on a clean counter and a rolling pin. Roll the dough out to ¼-inch thick. Use a 2½-inch round cookie cutter (flour this as well to keep it from sticking) and cut out the cookies.
Bake the cookies on the prepared baking sheet for 7 to 10 minutes. You want them to be set (no longer glossy), but not turning brown.
Transfer the cookies to a wire rack and let them cool completely.
Add the caramel bits and milk to a medium-sized, microwave-safe bowl and microwave for 1 minute. Stir well, then heat at 20-second intervals just until smooth. Stir in the salt.
11 ounces Kraft caramel bits, 1 tablespoon whole milk, ¼ teaspoon salt
Place 1 teaspoon of the caramel mixture onto each cookie. Use the spoon to swirl this in a circle on the top, leaving an empty border around the edge of the cookie. You want this to firm up before adding the chocolate. It will take up to ½ hour at room temperature, or you may place them in the fridge to speed it up.
Stir together the chocolate chips and the vegetable oil in a microwave-safe bowl and microwave at 30 seconds intervals, stirring between each one until smooth.
1½ cups milk chocolate chips, 1 teaspoon vegetable oil
Place one teaspoon of melted chocolate on top of the set caramel. Again, swirl it into a circle on top, mostly covering the caramel, leaving a border around the edge of the cookie. Feel free to top with flaky salt, if desired!
Once the chocolate is set (again, you can speed this up by refrigerating them), you may finally enjoy eating them!