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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. 4 stars
    These were delicious but very large. Could I cut the caramels in half and use half a tablespoon of dough?
    Thanks!

    1. Hey Frances,
      Thanks so much for giving the recipe a try, I am thrilled that it worked out for you! Yes, you could do that. Happy Holidays! xTieghan

  2. 5 stars
    I will adit I was nervous to make these based on others comments about them turning into puddles. While these were not the easiest cookies I have ever made. I chilled the dough as recommended and yes while the dough does warm up quickly when rolling and making the cookies and it was tedious – these turned out perfectly and were DELICIOUS. I made these for friends for cookie tins for the holidays and everyone LOVED them. Even though they were messy when rolling the dough, I would highly suggest that you give these guys a try. I had to keep an eye on them and bake longer then suggested but they did set up even more after removing from oven as noted in the recipe. While I claimed while making I would not make again, I seriously rethought that after tasting them. I did not get 24 cookies out of my batch, so I would not suggest unwrapping all the chocolates before you start as I have now have a bowl of chocolates in my fridge (which will of course get eaten :)).

    1. Hey Megan,
      Thanks so much for giving the recipe a try, I am thrilled that it worked out for you! Happy Holidays! xTieghan

  3. 4 stars
    Important note! I read the comments about the recipe being off (not enough flour). Do not add more flour! I too had a very “brownie batter” consistency, got nervous, and added an additional 1/2c flour. This was not necessary. After 2 hours in the fridge, the dough rolled just fine – and I assume would have without the extra flour. The cookies still turned out well, but I wish I would have just trusted the process. Figured I’d comment to help anyone else with this concern!

  4. Hello All,
    I figured it was a typo and added an additional cup of flour. I had
    the consistency of icing sugar, no way to form into 2 balls!

    1. Hey Nili,
      Sorry about this, like stated previously, there is no typo in the recipe, you should follow the ingredient list as is. I hope you love the recipe, please let me know if you have any other questions! Happy Holidays! xTieghan

  5. 5 stars
    Great recipe! Definitely a fave! I didn’t have the same problems as others, in that it was too runny. I went ahead and chilled in the freezer for 1 hour like some suggested, and that did it (I probably could have chilled for 30 minutes in the freezer)! I also melted the chocolate and butter on the stove, and used Ghirardelli chocolate and Lindt chocolate. No need for extra flour! Hope this helps others!

    1. Hey Shirley,
      I would freeze the dough and then thaw slightly to roll the balls. I hope you love the recipe, please let me know if you have any other questions! Happy Holidays! xTieghan

    1. Hey Linda,
      So sorry you had issues with the dough, my guess is it needed to chill longer:) I hope this helps for next time! xTieghan

  6. So before reading the comments, i noticed that the liquid to flour ratio seemed way out of wack. I basically cut the melted chocolate in half (reserved half the chocolate chips to just use as a mix in) and chilled the dough in the fridge for about 2 hrs. Perfect consistency and a great bake after about 10 mins at 350 and 2 mins with the oven off. I did two batches. the second batch was harder as i left the dough out while the first batch baked so about 15 mins total. It became a little more liquidy and then when baking the cookies certainly spread more! So chilling is crucial to this recipe as is cutting down the liquid. otherwise, delicious – i used andys candy instead of caramel because my husband loves mint 🙂

    1. Hey Alexandra,
      Thanks so much for giving the recipe a try, I am glad you enjoyed the cookies! Happy Holidays! xTieghan

  7. These cookies are next level AH-MAZING!!! I made them with the Ghirardelli mini squares and I liked the way they fit in the cookie better than the Dove chocolates. I also made some with the peppermint bark squares (omit salt on top) and that was an excellent festive spin on them as well!

  8. 5 stars
    Definitely need to add 2 Cups of flour…not 1/2 Cup flour or else it’s more of a runny consistency! By adding 2 cups of flour it actually formed into a ball! Can’t wait to taste them!

    1. Hey Carla,
      Hope these turned out okay for you…but it is only 1/2 cup of flour:) I hope you loved the recipe! Happy Holidays! xTieghan

  9. 5 stars
    These cookies are every bit as delicious as described! Mmmmm. they have just the right mix of sweet and salty to satisfy that sweet tooth.

  10. My batter on these cookies came out very soft and runny and I thought I had made a mistake, but once I chilled the dough thoroughly the cookies turned out beautifully and delicious!

  11. Hi,
    I think the recipe is perfect, although as a German I am used to weigh ingredients and I also recommend doing it here. I used 115g butter, 100g milk chocolate, 300g semi-sweet chocolate, 100g brown sugar, 3 eggs, vanilla, 90g flour, a pinch of salt for the dough. I am using a less chocolate here than in the original recipe and I forgot the coffee granules and the cocoa. The dough was messy, but I put it in the freezer for about an hour before working with it. My hands were full of chocolate when working with it an I only made about 6 – 8 cookies at once, then put the dough and the cookies back into the freezer. They turned out great and did not spread! The only thing I will change next time is to add the coffee and to use square caramels. I did use rectangle ones and the cookies turned more oval than round. I did get 31 cookies with my recipe.

    1. Hi! Thank you so much for trying this recipe, I am glad the cookies turned out well for you! If there is anything I can help with, please let me know! xTieghan