Line a couple of baking sheets with parchment paper, or we prefer silpats.
In the bowl of a stand mixer or a regular mixing bowl, beat the butter until creamy, about 20 seconds.
¾ Cup Butter
Add the shortening and sugar and continue to beat for a couple minutes until light and fluffy. We always have to scrape down the sides of the bowl.
¼ Cup Shortening, 1 ½ Cups Sugar
Add the 2 eggs and vanilla and mix well.
2 Eggs, 1 teaspoon Vanilla Extract
In a separate bowl, whisk together the flour, cocoa, cream of tartar, baking soda, baking powder, cinnamon and salt.
2 ¾ Cups Flour, ½ Cup Unsweetened Cocoa Powder, 1 ½ teaspoons Cream of Tartar, 1 teaspoon Baking Soda, ½ teaspoon Baking Powder, ¼ teaspoon Cinnamon, ½ teaspoon Salt
Turn the mixer on low and slowly beat in the flour mixture. Mix until combined.
Using a cookie scoop, scoop out the dough into your hand and make a deep indentation in the dough. Using a teaspoon, place a dollop of dulce de leche in the middle and close the dough around the caramel.
½ Cup Dulce De Leche
Shape the dough into round balls and roll in the cinnamon sugar.
⅓ Cup Cinnamon Sugar for rolling
Do not freeze this dough with the caramel or it will melt into the cookie and not be noticeable.
Place the sugared dough on the prepared cookie sheets.
Bake at 350℉ for about 8-10 minutes, or until the edges are set.
Let rest on the baking sheet for about a minute so you don't burn your tongue on the caramel.
While they are cooling, sprinkle the tops with a little more cinnamon sugar.
Transfer the cookies to a wire rack to cool.
Best eaten while still warm!
Video
Notes
These cookies freeze well as dough balls, but you'd need to let them defrost and then fill with dulce de leche and roll in cinnamon sugar or the caramel melts into the cookie.