In a large bowl, add the softened butter, powdered sugar, and vanilla. Start off by mixing everything with an electric hand mixer on low speed, then pick it up to the highest speed once you don’t see any more dry patches of powdered sugar. Beat for a total of about 4 minutes.
Use a fine-mesh sieve to sift in the flour, baking powder, and salt. Mix on low until everything is well combined.
Place the cookie dough onto a piece of plastic wrap, flatten it to a disk, wrap it, and refrigerate for about 1-2 hours.
Dust your work surface with a little bit of flour. Use a rolling pin to roll the chilled dough to 1/2 inch thick.
Cut the cookies out using a 2-inch round cookie cutter. Bake the cut-out cookies on a parchment-lined baking sheet at 350°F (175°C) for about 6-8 minutes. These cookies are meant to be soft, so avoid over-baking.
Add the caramels and heavy cream to a bowl or saucepan and melt slowly until it’s smooth and runny. This can be done over low heat on the stove or in a microwave in 20-second intervals with mixing in between.
Melt the chocolate chips in a microwave-safe bowl in 20-second intervals, stirring in between.
Spoon a dollop of the melted caramel over each cookie. Once the caramel has cooled, smother the tops of each cookie with the melted chocolate. Optionally, add a sprinkle of flakey sea salt while the chocolate is still warm.