Combine Butter and Sugar in a large bowl. Beat until fluffy. Add vanilla, baking powder, and flour until just combined.

Wrap dough and chill for at least an hour (preferably overnight).

Preheat the oven to 350° Fahrenheit.

Roll out cookie dough to ¼ inch thickness. Cut out 2 ½ inch circles. Combine dough scraps and repeat this process until the dough has been depleted.

Bake for 7 to 10 minutes. Let cool on baking tray for 2-3 minutes before transferring to a cooling rack.

In a saucepot, combine light-corn syrup and granulated sugar. Place over a low heat to allow the sugar to dissolve.

In a small, microwave-safe bowl, combine heavy whipping cream and unsalted butter. In 30-second burst, melt the butter into the cream.

Boil the sugar until it reaches 245° Fahrenheit. Then add in the heavy whipping cream mixture while the heavy whipping cream is still hot.

Let cool to 100° Fahrenheit. Add a tablespoon of caramel to the top of each cookie. Let cool completely.

In a microwave-safe bowl, combine milk chocolate and vegetable oil. In 15-second burst, melt the chocolate until smooth.

Place one tablespoon of chocolate on each cookie. Spread if needed. Let set by cooling completely.