Caramel Brownie Thumbprint Cookies are rich, chocolatey cookies that are filled with a smooth and creamy caramel filling and topped with a simple chocolate drizzle. Delicious cookie recipe that tastes just like a brownie with caramel on top.
MAKE THE CHOCOLATE COOKIES: Line two large baking sheets with parchment paper or silicone baking mats and set aside.
Whisk together the flour, cocoa powder, salt, and baking powder in a medium size bowl. Set aside.
Cream together the butter and both sugars on medium-high speed until light and fluffy, about 2-3 minutes.
Add the egg yolk and the vanilla then beat again for about 2-3 minutes. Scrape down the sides of the bowl as necessary.
Turn the mixer speed to low, then slowly add the dry ingredients, mixing until just combined.
Using a small cookie scoop, drop mounds of cookie dough onto the prepared baking sheets until you have used up all of the dough.
Using a 1/4 or 1/2 teaspoon measuring spoon, gently press down on the tops of the dough balls to create an indent.
If the spoon is sticking to the dough, dip it in a little bit of cocoa powder.
Once all of the cookie dough balls have been indented, chill in the refrigerator for at least 1 hour.
Preheat the oven to 350ºF and then bake the cookies for 9 to 11 minutes until the edges are set.
Remove the cookies from the oven, then press down gently again with the measuring spoon to re-shape the wells while the cookies are still hot. Make sure not to press too hard!
Allow the cookies to cool for at least 5 minutes on the baking sheet before transferring to a cooling rack to cool completely before filling with caramel.
MAKE THE CARAMEL FILLING: In a small bowl with a spout (preferably a glass measuring cup with a spout), combine the unwrapped caramels, 2 teaspoons of milk, and salt.
Melt in the microwave on high for 30 seconds, stir, then continue to microwave in 15 second intervals, stirring after each, until you have a smooth, pourable mixture.
Add an additional ½ teaspoon of milk if you need to thin it out more.
FILL THE COOKIES: While the caramel is still very warm, slowly and carefully fill each chocolate cookie, taking care not to overfill the wells.
The caramel will spread to the edges, so only fill it about halfway before adding more to fill to the brim.
DRIZZLE WITH CHOCOLATE: Allow the caramel to set before drizzling with chocolate. Place the chocolate in a small microwaveable bowl and microwave for about 20 seconds. Stir and then microwave in 10 second intervals, stirring after each until the chocolate is completely melted and smooth. Drizzle over the set caramel.