Top Twelve Days of Christmas Cookies: Chocolate Caramel Thumbprint Cookies

Chocolate Caramel Thumbprints 1

DAY 12: Chocolate Caramel Thumbprint Cookies

Four of my five children voted this cookie as their favorite all-time Christmas cookie.

I like to make these cookies with a homemade caramel filling. With a candy thermometer, the caramel filling comes together quickly and turns a good cookie into a fabulous one!

You can also make the filling with melted packaged caramels. If you want to take the “easy” route and buy a bag of Kraft Caramels, that recipe can be found HERE.

Here is my tip for getting a good deep pocket for all of that amazing caramel: Use the back of a rounded measuring spoon and press it into the center of each cookie. I use a ½ teaspoon measuring spoon on the raw cookie dough before baking:

Chocolate Caramel Thumbprints 2

Then I use  a 1 teaspoon measuring spoon on the hot, baked cookie. (The cookies do spread a little when they are baked, leaving a larger opening). This is a good alternative to actually using (and burning) your thumbs.

Chocolate Caramel Thumbprints 3


      (2017): Chocolate Caramel Thumbprint Cookies with Homemade Caramel Filling

     (2009): Chocolate Caramel Thumbprint Cookies with Filling made from Packaged Caramels


Chocolate Caramel Thumbprint Cookies

Chocolate Caramel Thumbprints 1

1 cup butter, softened
1 1/3 cups sugar
2 eggs, separated
¼ cup milk
2 tsp vanilla extract
2 cups flour
2/3 cup cocoa powder
½ tsp salt
2 cups finely chopped pecans

Homemade Caramel Filling (recipe below)

1 cup bittersweet chocolate chips
2 Tbs butter
2 Tbs corn syrup

Prepare Cookies: Combine butter, sugar, egg yolks, milk, and vanilla in a mixing bowl. Beat until light and fluffy. Add flour, cocoa powder, and salt. Beat until well combined. Refrigerate dough for 1 hour.

Preheat oven to 350°F. Place egg whites in a small bowl. Place finely chopped pecans in a bowl. Set aside. Roll dough into balls. Dip balls into egg white and then into pecans. (I find this easier if I make a whole baking sheet worth of dough balls, then dip them in egg/pecans). Place on a parchment paper lined baking sheet. Make a small indentation in the center of each cookie with the back of measuring spoon (I use a ½ teaspoon) or your thumb.

Bake at 350°F for 12 minutes, or until cookies are set.

While cookies are still hot, press center again (use the back of a round 1 teaspoon measuring spoon). Cool.

Prepare Caramel Filling (recipe below).
Spoon small amount of warm caramel into centers of baked cookies. Carefully remove cookies to a wire rack to cool.

Prepare Chocolate Glaze: Combine bittersweet chips, butter, and corn syrup in a small bowl. Microwave for 30 seconds. Stir. Microwave for another 20-30 seconds if not melted. Let cool slightly. Pour chocolate into a small Ziploc freezer bag. Poke a hole in the corner of the bag (a bamboo skewer makes a perfect sized hole). Drizzle chocolate over the cooled cookies. Cool until set.

To store: refrigerate or freeze cookies in individual layers; then store between layers of waxed paper in the refrigerator or freezer. They can also be stored at room temperature, but if you stack them, they will stick together.

Homemade Caramel Filling

1 cup unsalted butter
1 can sweetened condensed milk
2 cups brown sugar (light or dark)
1 cup light corn syrup
2 Tbs heavy cream
2 tsp vanilla extract
½ tsp sea salt

Combine butter, sweetened condensed milk, brown sugar, corn syrup, and heavy cream in a large saucepan. Bring to a boil over medium heat. Place a candy thermometer on the side of the pan. Reduce heat to medium low, maintaining a low but continuous simmer, until caramel reaches 235°F (soft ball stage), stirring occasionally. This will take about 20 minutes. Remove from heat and stir in vanilla and salt.


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