Preheat oven to 350°F (175°C). Line baking sheets with parchment paper or silicone liners.
Cut each caramel in half and set side.
Whisk together the flour, cocoa, baking powder, and salt. Set aside.
Using an electric mixer on medium speed, beat the butter until light and fluffy. Add the sugars and mix well. Mix in the egg and egg yolk; then, add vanilla.
Reduce the mixer speed to low. Add the flour mixture and mix just until combined.
Form a tablespoon of dough into a circle. Place 2 caramel halves in the center of the circle. Fold the dough around the caramels, making sure to seal well. Place each cookie on the prepared pans, leaving about 2 inches between cookies.
Bake one pan at a time for 10 to 12 minutes or until the cookies are set.
Cool the cookies on the pans on wire racks for 5 minutes. Then transfer the cookies from the pans directly onto a wire rack to cool completely.
Notes
Recipe adapted from The Ultimate Chocolate Cookie Book.
Store chocolate caramel cookies in an airtight container at room temperature for 3 to 4 days. You can heat them in the microwave for a few seconds to make the middles gooey if you’d like.