Preheat the oven to 375°F. Line two cookie sheets with silicone baking mats.
In a medium bowl, beat together the butter, brown sugar, and granulated sugar until creamy, about 1 minute. Add the egg yolks and vanilla, and mix until combined.
In a separate small bowl, whisk together the flour, instant espresso, baking powder, and fine salt.
Add the dry ingredients to the wet ingredients and mix until just combined. Stir in the chocolate chips by hand.
Flatten the dough in the bowl, then divide it into quarters. Divide each quarter into 3 pieces, forming a total of 12 cookies. Roll each piece into a ball and place them on the prepared cookie sheets, leaving space between each cookie.
Cut each Werther’s Original Chewy Caramel into four pieces. Press 2 pieces into the center of each cookie dough ball, keeping them close together.
Use your fingers to pile the dough high on itself to help prevent spreading while baking.
Bake for 9 minutes. Remove from the oven and press additional caramel pieces and chocolate chips into each cookie. Sprinkle flaky salt over each cookie.
Allow the cookies to cool on the baking sheet for 2 minutes before transferring them to a wire rack to cool completely. Enjoy your delightful puddle cookies!