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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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This post was originally published on November 3, 2020
3.99 from 564 votes (475 ratings without comment)

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Comments

  1. 5 stars
    Followed the recipe exactly as written and they turned out amazing!! I baked a small batch and froze the rest so I can keep enjoying fresh out the oven cookies:)

  2. I am making these cookies, as I make so many of your recipes but the recipe says 1/2 cup plus 2 Tbs flour. My mix is like batter, not dough. I am thinking maybe it should be
    1 1/2 cups flour plus 2 tbs. typo?

    1. Hey Nan,
      No typo, just be sure to freeze the batter and you should be good to go! I hope you love the recipe, please let me know if you have any other questions! xTieghan

  3. 3 stars
    I would have to agree with the others that commented on this. I tried out this recipe and rather than it becoming a dough, it was more like a brownie batter. Ended up adding about 2 more cups of flour. After altering the recipe a little bit, the cookies ended up turning out really well & they tasted super good.

  4. I wish I would have just stuck to the recipe! I got worried when the batter was brownie like and the recipe read to separate in to two balls, totally impossible… so I read the reviews that commented to increase the flour, which I did and totally ruined the batter. It seemed to be going okay until I baked the cookies which tasted super dense and hard. They didn’t melt down or crackle. I will definitely just freeze the batter in the bowl next time and then roll in to balls from there.

  5. These were amazing! I made them for my daughter’s birthday and they were a big hit! I sprayed my hands with some cooking spray before working with the cool dough and didn’t get any dough stuck to my hands!

  6. The batter looked too loose like a brownie batter. So I added 2 cups of flour like someone else recommended and I wish I didn’t. They came out thick and cakey, not fudgy or crinkly like I imagine they are supposed to be. Next time, I’ll follow the recipe and see what happens! Sorry I doubted you!

    1. Hi Marcel! I am really sorry about that! I hope this turns out better for you the next time! Please let me know if there is anything I can help with! xTieghan

  7. 4 stars
    Delicious cookies but the dough as written in the original recipe was a bit too runny. While less flour should be required for a crinkle style cookie, I did need to add approx. 1/2 C of flour to feel confident the dough would actually be workable after refrigeration. I think the larger quantities of additional flour others have suggested may make the cookies more doughy than intended. That slight modification resulted in great results! i would have given 5 stars if not for the concern on the flour measurement.

  8. Echoing the rest. Once the batter was mixed i actually looked up comments because i thought, “this can’t be right!”…however i would not recommend adding 2 cups of flour. Must be a sweet spot in there. I tried adding flour to equal 2 cups and they came out great BUT not like the photo or what I think would be the ideal consistency….good, super tasty, but less flour than i did, more than the recommendation. Next time i will try with just one cup total.

    1. Hi Amy! I am sorry you had trouble with this one! I hope one cup turns out perfectly for you the next time. I would love to help with any questions you have! xTieghan

  9. 5 stars
    These are so delicious. I left the salt off and didn’t use the instant coffee but they still taste so good. It was a bit confusing when my cookie dough turned out icing like but I think it’s because I didn’t cool the chocolate enough before mixing it all. I left the bowl of dough in the fridge overnight and it was workable the next day.

  10. 5 stars
    A little tricky to work with as it was very sticky. But I’m glad I worked through it because it as delicious in the end.

  11. 5 stars
    These are some of the very best cookies that I have ever had the pleasure of making. They taste as good as they look. I will be making these as a bring along dish for the holidays.

  12. I made these a week ago. Seriously so so yummy! The recipe was easy to follow and did not take a long time. I will be making these again soon! Maybe for Thanksgiving! Thanks!

  13. 5 stars
    My second batch turned out perfect! For those who said they had to add more flour, don’t! I did that on my first try and the cookies were terrible. Follow the recipe to the T and freeze it for an hour to help firm up.

    Thanks, Tiegen!