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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. Hey Marylea,
      The oven temp is listed in step 2, 350 degrees:) I hope you love the recipe, please let me know if you have any other questions. Happy Holidays! xTieghan

    1. Hey Melissa,
      That is listed in step 2, 350 degrees. I hope you love the recipe, please let me know if you have any other questions. Happy Holidays! xTieghan

  1. 5 stars
    I wanted to comment and give some feedback on the ingredient question. I made these cookies the other day and at first, I thought something might be wrong with the recipe. The batter had almost a frosting-like consistency and I double-checked my measurements a few times just to make sure I wasn’t missing anything. Then I chilled the batter as the recipe says. When I tried to roll them into the balls, add the caramels, etc. it was a mess. It was hard to work with and the warmer the batter got the harder it was to roll them. It covered my hands and stuck to everything as I tried to quickly make a bunch of cookie balls. I popped them into the oven and while I waited I looked at the comment section to see if anyone else had this experience and they did. I was bummed thinking I should have added flour because there must have been a typo.

    I am here to say the recipe is perfect as is with the ½ cup and 2 tablespoons of flour! My cookies came out PERFECT! They are perfectly gooey with a brownie-like taste. My boyfriend said they are his favorite cookies now. So, despite the pain they were to work with I will be making them again and I will follow the exact ingredient list above!

    *Next time I may even split the batter into 3 or 4 parts and work in smaller batches so it’s as close to chilled before I work with it.

  2. The recipe as written is perfect. Don’t add any more flour than it calls for. 1/2 cup plus 2 tablespoons. The magic happens when you put the batter in the refrigerator. It turns into a dough. I was skeptical at first just like a lot of other commenters…but it really does turn into a dough. So yummy!

  3. I am in the middle of making these and my dough did not form a ball at all! It looks like I should be pouring it into a pan to make brownies.. help!!

    1. Hey Sadie,
      Yes, you need to chill the batter until solid. I hope you love the recipe, please let me know if you have any other questions. Happy Holidays! xTieghan

  4. My comment is that this recipe is amazing IF you follow the ingredient proportions to a T! It is very confusing where the recipe says “divide the dough in half” because when first mixed it will be much closer to brownie batter than dough. Once chilled, the dough becomes totally workable. I made the mistake of following some reviewers suggestions to add more flour and that was a huge mistake. They will not come out crinkly and cookie-like if you do that. I re-did the recipe without making alterations, let chill, and voila the cookies came out perfectly!!! My only question is there a way to get them looking darker brown like pictured? My cookies were much lighter in color. Thank you!

    1. Hey Vivian,
      Thanks for giving the recipe a try, I am glad you enjoyed. Try using a different brand of chocolate for a darker look. Please let me know if you have any other questions! Happy Holidays! xTieghan

  5. 5 stars
    These cookies were even better than expected! They are so rich and chocolatey! I love the gooey caramel center and the salt on top. It’s honestly everything I’ve ever wanted in a cookie. They definitely take patience to make, but I think it’s worth the time and effort.

  6. 5 stars
    Hi! I just popped six of these into the oven and they are absolutely INCREDIBLE!!! So beyond delicious and decadent! I followed the recipe to a T, chilled overnight in the fridge, and they look great! I did have a question though! Since the dough needs to be rechilled after every few cookies, and I only have two people in my house, how long do you think they dough would last in the fridge? I would love to be able to pop a few in the oven each night for dessert!

    1. Hey Mary,
      Thanks so much for giving the recipe a try! I would say no more than 1 week in the fridge, but you could certainly freeze them. Please let me know if you have any other questions. Happy Holidays! xTieghan

  7. 3 stars
    I made these today but ran into issues with the consistency of the dough. It was way too runny to form into balls before chilling and looked more like cake batter. After reading other comments on here that some had trouble with their cookies spreading out all over the baking sheets, even after chilling, I decided to add more flour to the dough instead of only 1/2 cup + 2 tbsp like it says, was this a typo? I ended up adding almost 2 more cups of flour to make it thicker and then I added an extra 1/4 tsp of baking soda since there was more flour. I didn’t need to chill the dough as long after adding more flour and was able to cover a chocolate covered caramel with only one tbsp of dough vs. two. With the extra flour in the dough I still baked the cookies for 10 minutes and they turned out great! The insides were a little gooey but the cookies puffed up very nicely! All in all, this is a good recipe but I just wonder about the correct amount of flour. I’m a big fan of HBH and love your recipes! Thank you! 🙂

    1. Hi Bailee! I am really glad these turned out well for you. Yes, that is the amount of flour that I used and works for me. Please let me know if there are any other questions I can help with! xTieghan

  8. 4 stars
    I really like these cookies, but the caramel melted through the bottom even though the dough completely enclosed them. Do you have any suggestions for this? Thanks!

    1. Hey Becca,
      Thanks for giving the recipe a try, that is just part of the cookie:) I hope you love the recipe, please let me know if you have any other questions. Happy Holidays! xTieghan

  9. 5 stars
    These are so delicious. I did have a hard time working with the dough. It was kind of crumbly and sticky. But worth it.

  10. 3 stars
    The recipe is good, although there is a typo in the recipe when it comes to amount of flour. I’ve read through the comments and went with 2,5 cups of flour instead of 0,5 cup and it worked fine, but left my cookies rather cake-y. Still good 🙂

  11. 3 stars
    While the cookies had good flavor, I had the same issue as many below – the dough had an icing-like consistency and was difficult to roll into balls without making a huge mess. After trying two separate times (one sitting overnight in the fridge and one sitting in the freezer for 30 mins), I agree it must be something with the recipe!

    1. Hey Hannah,
      Thanks so much for giving the recipe a try, I am sorry you had issues with the batter. I would pop it in the freezer so it is easier to roll. I hope this helps for next time! xTieghan

  12. Pretty sure something is wrong in the recipe. The dough turned into a solid chunk of chocolate, which probably means it needs more flour. I would not recommend the recipe as written.