Chocolate Cookies with Salted Cinnamon Caramel

 They might not be the prettiest cookies on the block, but they definitely tasted awesome!  I know, because I brought them to work and they disappeared within an hour in the teachers' room.  (well, I guess it's possible that everyone tried them, but didn't like them.  I wasn't there to see reactions, but I assume they were positive! haha)

Lessons for next time:

1. Get a small scoop so that they could be a uniform size.  The only cookie scoop I had was too big, so I had to eyeball it
2. Get a round-ended spoon to make the indentations.  All I had was a squarish one, so I went with square cookies.  Circles would have looked a lot better
3. Roll the dough in your hands a bit to minimize the crackling. I thought they would even out while baking, but they looked exactly the same coming out as they did going in.
4. Make extra caramel- that stuff is amazing!!

For about 2 dozen cookies....

Ingredients:
1 ¼ cup all purpose flour
¼ cup Dutch processed cocoa powder, sifted
½ tsp kosher salt
1 stick (8 tbsp; 113g) unsalted butter, at room temperature
½ cup dark brown sugar, packed
1 tsp pure vanilla extract (I used vanilla bean paste)
2 tbsp milk, at room temperature
4 oz soft caramel (I used the Werther's brand soft caramels)
2 tbsp whipping cream
Cinnamon, to taste (I'm not sure how much I used, but I used a lot! I love cinnamon)
Salt (I used Maldon Sea Salt Flakes)

Directions:

1. Center an oven rack and preheat the oven to 325F.  Line cookie sheets with parchment paper or silicone mats. 
2. In a small bowl, whisk together the all-purpose flour, cocoa, and salt to combine. Set aside. 
3. In a medium bowl, using an electric mixer, beat the butter until fluffy. Gradually beat in the sugar and continue mixing until light and well combined. 
4. Add the vanilla, then milk. 
5. Add the dry ingredients and mix on the low speed just until the dough forms.
6. Roll the dough into 1-inch balls. Place them onto the prepared baking sheet and flatten very slightly with your hand. Using a handle of a wooden spoon, make an indentation in the center of each cookie; make it quite deep and about a penny in diameter. 
7. Chill the formed cookies for 20 minutes in the refrigerator, covered with parchment or plastic, before baking. 
8. Bake the cookies for 15 minutes, until the cookies appear set. Transfer the cookies on the sheet on a cooling rack and, using the same spoon handle, deepen the indentations made earlier; don’t poke through though, be gentle. You do want this extra space for a delicious filling. Let them cool completely
9. Put the caramel and the cream into a small microwave-safe bowl. Microwave on “medium” for about a minute, pausing the microwave and stirring a couple of times, until the caramel is melted and mixture is smooth. 
10. Transfer into a small plastic bag, seal to close. Snip a corner of the bag and fill the cookies. 
11. Top with salt. The cookies can be stored for up to a week in an airtight container.

 

Recipe adapted from Baking Obsession