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Everyone’s favorite…Crinkly Caramel Stuffed Brownie Cookies…for your Tuesday night pre-holiday cookie baking. Homemade crinkly brownie cookies, made with sweet milk chocolate, a touch of coffee, stuffed with gooey chocolate-covered caramels, then baked to perfection. Each cookie is finished with flaky sea salt for a cookie that’s salty, sweet, and dangerously delicious. Each bite is crisp and crinkly on the top, but soft and gooey in the center. There’s nothing not to love about these sweet crinkly caramel stuffed brownie cookies.

overhead photo of Crinkly Caramel Stuffed Brownie Cookies | halfbakedharvest.com

Happy Tuesday everyone!! I thought we’d brighten up the day with some of my favorite cookies. These are truly that melt in your mouth cookie that we could all use today.

These cookies, plus a warm mug of hot chocolate, or maybe a pumpkin latte. Yes, sounds like the perfect way to de-stress. Whether it’s today, tomorrow, or throughout this busy end of the year holiday season, these should be your go-to. They’re sweet, perfectly hinted with coffee, and stuffed with delicious milk chocolate caramel chunks.

prep photo of Caramel Stuffed Brownie Cookie before baking

One of my favorite cookies – and my family’s too. Already excited to include these in my 2020 holiday cookie box in just a few short weeks! I know it’s only November 3rd, but I’m officially kicking the holiday baking season off with these cookies. They’re decadent in all the best ways. And yes, you do need to make them, preferably several times over the next few weeks! As I’ve already said, this year needs all the holiday cheer we can give it, so why not start a little early. Right?!

And with that, let’s get to the details!

prep photo of Caramel Stuffed Brownie Cookies before baking

Everything you need to know about baking these cookies.

First things first, start with the chocolate. You need a lot of it. I used a mix of milk chocolate, semi-sweet chocolate, and even some cocoa powder. I really wanted these cookies to resemble my favorite crinkle top brownies, so I used a very similar set of ingredients for the dough.

Simply melt together salted butter (my baking secret) with both of the chocolates. It’s going to seem like a lot of chocolate, but trust me it’s all going to turn out great.

Once the chocolate is melted, beat the eggs until they’re light and creamy. This step is KEY if you want a crinkly cookie, so don’t skip it. Once you see the eggs turn pale in color, add in that melted chocolate, then all of the dry ingredients.

overhead photo of Crinkly Caramel Stuffed Brownie Cookies

Mix and done, that’s your brownie-cookie dough.

So simple. But here’s the hard part, we need to chill the dough to help it stiffen up before rolling it out. To speed up the process, I just stash the dough in the freezer for thirty minutes until it’s firmed up.

Once the dough is chilled, roll it out, and stuff each dough ball with a sweet milk chocolate caramel, then bake!

side angled close up photo of Crinkly Caramel Stuffed Brownie Cookies

What I love about these cookies is that they’re easy to make, but yet they feel fancy. Everyone thinks they likely took hours to make, when they’re actually super simple.

But my favorite part? These are just perfectly crinkly on top, but also soft and gooey in the center, with caramel melting out. The best kind of cookie…decadent. But it’s what we need today. Perfect for Tuesday baking, our Thanksgiving table, holiday cookies boxes, and Christmas baking.

So, what do you think? Tuesday night baking?

Then take the leftovers to work and make everyone’s day. You should do this. It is the season of giving!

overhead close up photo of Crinkly Caramel Stuffed Brownie Cookies

Looking for other Thanksgiving cookie recipes? Here are my favorites: 

Chai Spiced Maple Sugar Cookies with Browned Butter Frosting

Slice n’ Bake Salted Chocolate Butter Pecan Cookies

Pecan Pie Cookies with Butter Pecan Frosting

Lastly, if you make this Crinkly Caramel Stuffed Brownie Cookies, be sure to leave a comment and/or give this recipe a rating! Above all, I love to hear from you guys and always do my best to respond to each and every comment. And of course, if you do make this recipe, don’t forget to tag me on Instagram! Looking through the photos of recipes you all have made is my favorite!

Crinkly Caramel Stuffed Brownie Cookies

Prep Time 20 minutes
Cook Time 10 minutes
Total Time 1 hour 30 minutes
Servings: 24 cookies
Calories Per Serving: 456 kcal

Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.

Ingredients

Instructions

  • 1. In a microwave-safe bowl or glass measuring cup, melt together the butter, milk chocolate, and chocolate chips until melted and smooth. Let cool completely. *This can also be done on the stove.
    2. In a large mixing bowl, beat together the eggs and sugar, beating on high until pale in color, about 3 minutes. Add in vanilla extract, instant coffee (if using), and the melted chocolate/butter, beating until combined. Add the flour, cocoa powder, baking soda, and salt, mix until just combined. The batter with be very loose. Divide the dough in half. Cover each ball of dough and chill 1-2 hours in the fridge or overnight, until firm. Preheat the oven to 350° F. Line a baking sheet with parchment paper. 
    3. Working with 1 dough ball at a time (leave the other in the fridge), roll the dough into tablespoon size balls. Flatten the dough slightly into a round and add the chocolate covered caramel. Scoop another tablespoon of dough out and flatten it slightly. Place the dough over the caramel, sealing the edges together. Place 3 inches apart on the prepared baking sheet. If the dough softens, stick it in the freezer for a few minutes to re-chill it.
    4. Bake for 10-14 minutes, until just set on the edges, but puffed in the center. Let the cookies cool on the baking sheet. They will continue to cook slightly as they sit on the baking sheet. Sprinkle with flaky salt (if desired). Eat warm (highly recommended) or let cool and store in an airtight container for up to 4 days. 

Notes

Caramels: I use Dove milk chocolate caramels
Freezing: the cookie dough balls can be frozen for up to 3 months. Thaw, then bake as directed. 
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Comments

  1. Hello! I followed the recipe, but after cooking the first one I’ve ended up with really cakey cookies sadly instead of chewy! Is there anyway to fix the dough I have already made so they will come out chewy?

    1. Hi Samantha,
      While the cookies are baking, try pulling them from the oven and tapping the baking sheet on the counter. That should help! I hope you love them! xx

    1. Hey Marissa,
      Wonderful!! I love to hear that this recipe turned out well for you and thanks so much for trying it out! Yes, an equal amount of gluten free flour will work well for you! xx

  2. Hi Teighan, excited to make these for Christmas! Would you recommend freezing the chocolate caramels prior to baking?

    1. Hey Heather,
      Nope, no need to freeze the caramels:) Please let me know if you give this recipe a try, I hope you love it! xT

    1. Hey Mackenzie,
      Happy Holidays!! I love to hear that this recipe was enjoyed and appreciate you giving it a try! 🎄❄️

  3. 5 stars
    These turned out so delicious! And they are so easy to make! I was a little skeptical with the dough before I chilled it because it was so sticky!! But it worked great for wrapping around the chocolates and rolling up after it was chilled. And the finished cookies with a little sea salt are incredible!!

    1. Hey Christie,
      Happy Holidays!! I love to hear that this recipe was enjoyed and appreciate you giving it a try! 🎄❄️

    1. Hey Ginger,
      Happy Wednesday!!❄️ So glad to hear that this recipe was enjoyed, thanks so much for making it and sharing your feedback! xT

    1. Hey Nancy,
      Sure, that will work well for you! Please let me know if you have any other questions, I hope you love this recipe! xx

  4. Hi! Why are both chocolate and chocolate chips used? What are the advantages to this and could I sub the chocolate chips for regular chocolate? Thanks in advance! 🙂

    1. Hi Noor,
      I like the balance from the semi sweet chocolate and the milk chocolate:) You could use all chips but I would give a combo of flavors here. Please let me know if you give this recipe a try! xx

  5. 5 stars
    I loved these cookies! I don’t know why but mine appeared to be more of a cake texture and didn’t flatten or have the crinkly top. That said A+ for taste even if this baker failed on the aesthetic.

    1. Hey Gabriella,
      Happy Monday!!☃️ I truly appreciate you making this recipe and sharing your review, so glad it was enjoyed! xT

    1. Hi Ileen,
      So sorry, I haven’t, I would recommend following the recipe as written for best results. Please let me know if you have any other questions! xT

      1. Hi Tieghan, I made my cookie dough over the weekend and placed it in the fridge until I’m ready to bake them. After you have placed the second flatten tablespoon of dough over the caramel chocolate do you roll your dough back into a ball prior to baking? Thanks so much, I’m excited to bring these to Christmas this weekend. Happy Holidays. Ileen

        1. Hey Ileen,
          I guess they never go back into a true ball, you kind of form the second layer of dough around the caramel if that makes sense! I hope you love this recipe, please let me know if you give this recipe a try! xx

    1. Hey Beth,
      So sorry, I haven’t, but I don’t see why that wouldn’t work for you! Let me know if you give this recipe a try, I hope you love it! xx

    1. Hi Althea,
      Yes, 1/2 cup of flour is correct. Please let me know if you give this recipe a try, I hope you love it! xx

  6. Hi Tieghan,
    I love all your recipes. I was hoping to make these and found a similar recipe in your cookbook, except it calls for unsalted butter and 4oz of bittersweet chocolate chopped, not milk or semi, which do you prefer? Do these make a big difference? Thanks!

    1. Hey Lori,
      These are 2 different recipes:) So you can really choose whichever sounds better for you! Chocolate is definitely a personal preference based on taste! Let me know if you give the recipe a try, I hope you love it! xT

  7. 5 stars
    Made these tonight, and it’s going to be a challenge to have them last two more days until Thanksgiving. They afraid delicious. I ended up making about 20 cookies (mine must have been extra large). Cooked for about 15 mins-perfection. Thanks, Tieghan!

    1. Hey Nancy,
      Wonderful!! Thanks so much for making this recipe, I love to hear that it was enjoyed!! Happy Thanksgiving! 🦃

  8. I’ve made cookies with a caramel center in the past, and once cooled, the caramel became very hard and less appealing. Are these still good at room temp?

    1. Hey Ashley,
      They should be just fine and not turn hard for you:) Please let me know if you have any other questions, I hope you love this recipe! xx

      1. 4 stars
        Update! I made these last night for an ornament exchange, and I got some high praise! I really liked them, but they were almost too sweet for me (not something I say very often). I didn’t add coffee because I don’t like the taste (and if I purchased some, I’d never make it through the whole bag), but I wonder if that would’ve cut the sweetness without giving much coffee flavor. What do you think?

        1. Hey Ashley,
          Happy Friday!!🌟 Love to hear that this recipe was tasty for you, thanks so much for trying it out! The coffee really enhances the chocolate flavor:) xT