Dark Chocolate Cookies Filled with Caramel

It has happened! We finally got some snow at the beginning of the week. And let’s be honest, nothing puts you into the Christmas mood more than the fluffy white stuff. With the flakes gently falling to the ground, I was basically drawn to the kitchen. And could I really have made anything besides cookies? Not just any old cookie would do – oh no, no, no! It had to be one of the best. A cookie that is chocolaty, rich and rolled in sprinkles. Lots and lots of sprinkles. It’s gonna be delicious!

Dark Chocolate Cookies Filled with Caramel by Deliciously Yum!

If you’re looking for another cookie to bake this Christmas season, look no further. Even if you think you have no time to bake this year, you should definitely reconsider and spread some Christmas cheer with these cookies. You will have no regrets. Nada. None. Whatsoever.

Caramel Chocolate Cookies by Deliciously Yum!

This is an all-time favorite recipe. A family classic. Last Sunday morning (as the snow started to fall), I mixed up the dough for these cookies and planned on taking it to my in-law’s house since we were gathering there to watch the Packers win their first game in a very long time! Upon arrival, I walked straight into the kitchen to finish baking these cookies. And who was standing at the counter unwrapping Rolos, which make up the caramel filling in the middle? My husband’s dad – helping his wife prepare a batch of these Chocolate Cookies. LOL! It’s a Christmas staple for sure!

Caramel Stuffed Chocolate Cookies by deliciouslyyum.com

There’s just nothing like a slightly crispy and chewy cookie that holds a surprise inside. I’m a huge fan of dark chocolate and always use special dark cocoa powder in my recipes; if you happen to like regular cocoa powder better or simply have it on hand, feel free to use it. It’ll work just fine.

Dark Chocolate Cookies Filled with Caramel more at deliciouslyyum.com

Did I mention that these are one of Santa’s favorites? You might as well bake a cookie that Santa will thoroughly enjoy with a tall glass of milk. It’s obvious why he adores these cookies – the festive sprinkles may or may not have catapulted these to the very top of his list, ha! I’ve also heard that parents and kids alike are huge fans of these sweet treats.

Caramel Filled Dark Chocolate Cookies by Deliciously Yum!

The man in the red suit has impeccable taste. I have a suspicion that we would get along very well. And I’m guessing so would you! Thinking of you and of everyone who reads my blog, brings a huge smile to my face. I wish I could stop by your house with a plate full of cookies and goodies and deliver them to you. You deserve a huge thank you. Thanks for sweeten my journey and making it so much fun. Have a marvelous Wednesday!

Dark Chocolate Cookies Filled with Caramel
Yields 48
Dark Chocolate Cookies wrapped around caramel chocolate candies. The perfect addition to your cookie jar!
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  1. 1 cup white sugar
  2. 1 cup brown sugar
  3. 1/2 cup unsalted butter, softened
  4. 1/2 cup shortening
  5. 2 eggs
  6. 2 teaspoons vanilla
  7. 3/4 cup cocoa (Hershey's special dark)
  8. 1 teaspoon baking soda
  9. 2 1/2 cups flour
  10. 1 bag Rolos (chocolate covered caramel candies)
  11. green and red sprinkles, mixed together
  1. Preheat oven to 350 degrees F and line two cookie sheets with parchment paper. Unwrap 48 Rolo candies and set aside. Mix sprinkles in a small bowl and set aside as well.
  2. 1. Cream together the white sugar, brown sugar, butter, shortening, eggs and vanilla. Stir in 3/4 cup cocoa until thoroughly combined. Finally add baking soda and flour (one cup at-a-time). Mix well.
  3. 2. Flatten 1 rounded tablespoon of dough around a "Rolo" candy. Roll ball in sprinkles and place cookie ball on a prepared sheet. Bake for 10-11 minutes. Let cookies cool on the cookie sheet for at least 10 minutes before moving them to cooling racks to finish cooling.
  1. Cookies will keep up to 5 days in an airtight container. They also freeze very well - keep in an airtight container or ziploc bag in the freezer for up to 2 months.
Deliciously Yum! http://deliciouslyyum.com/

6 thoughts on “Dark Chocolate Cookies Filled with Caramel

  1. Wow – just finished the long wait while they cooled properly and tasted the first one, these are even more delicious than they look! Plus they were fast & easy to make, perfect for my cookie exchange. Thanks for sharing, great recipe!

  2. They sound delicious, but I have a few questions:
    1. Here in the Nlds you can only buy Rolos in a roll, like mentos. How much is a bag of Rolos in weight?
    2. When you say “two teaspoons of vanilla”, do you mean vanilla essence, vanilla flavour, or vanilla sugar?

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