Add the vanilla and salt and beat until incorporated, scraping down the bottom and sides of the bowl as needed. Add the flour and beat on medium-low until just combined and the dough starts to combine together and pull away from the sides of the bowl. Cover the bowl with plastic wrap and chill for 30 minutes in the refrigerator.

Line a large baking sheet with parchment paper. Lightly flour a clean work surface and roll the dough out into 1/4 inch thick. Use a floured round cookie cutter to cut out the cookies. Gather the scrapes and re-roll the dough until it’s all gone. Arrange the cookies 1 inch apart on the baking sheet and chill for another 15-30 minutes.

Preheat the oven to 350°F. Bake the cookies for 10-12 minutes, until the edges are set and just barely turning golden brown. Allow them to cool for 5 minutes then transfer to a wire rack.

While they’re cooling, melt the caramel. Add the unwrapped caramel to a glass bowl with the heavy cream and microwave for 45 seconds. Stir and repeat until it’s just melted and bubbling. Don’t overcook it or the caramel will become hard when it cools. Immediately spoon 1 teaspoon of caramel onto each cookie and nudge it to the edges the best you can with the back of the spoon.

Melt the milk chocolate in a small microwave safe bowl in 30-second increments until melted and smooth. Spoon on top of the caramel and top immediately with gold leaf and flaky sea salt if desired. Allow the cookies to cool so the caramel and chocolate set.s