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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. 5 stars
    These are INCREDIBLE! Totally addicting and real easy to make. My kids helped me make these for Santa’s visit, though most were eaten before he arrived 🙂 I’ll definitely be making these again.

  2. 5 stars
    I followed the recipe to a t and they came out perfectly! My local stores were out of doves so I subbed with a slightly bigger chocolate bar, and used more dough to cover them, so I only got 16 cookies. If you bake these right, you honestly don’t even the caramels, in my opinion. Very rich and delicious – perfect for our Christmas Eve bake.

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

  3. I printed out the recipe when it first showed up and tried baking this with like so many others found it way to soft and batter-like. Wasn’t firm enough to ball up so I froze it for 2 hours and just scooped it out to stuff. The cookies spread all over and flattened with a little bump in the middle where the Dove Kiss was. Very sad. And it just tasted like flat brownie. I came back here to see if I missed something and see that you have revised the recipe a little but no mention of it. I would recommend that if you change a recipe and it’s different or revised, you should date the changes so people will know if the one they use is the best. I’ve seen where someone may even update a recipe months or years later for the better and make note of it so visitors will know.

    1. Hey Dominique,
      So sorry you had issues with the recipe, I hope you give them a try again! Happy Holidays! xTieghan

  4. 5 stars
    These are so good!! After reading all of the reviews, I froze the dough in the mixing bowl for an hour, then separated it into two balls, covered them with wax paper and put them back in the freezer overnight. This worked perfectly! My cookies turned out quite large, I would suggest for a smaller cookie, when making the cookies roll them into balls smaller than a tablespoon.

    1. Hey Clare,
      Thank you so much for trying these cookies, I am thrilled that they worked out for you! Happy Holidays! xTieghan

  5. 1 star
    I usually love your recipes, but this one went sideways! The butter to chocolate ratio in the first step seems off – I tried it three different times and the chocolate seized up and hardened each time. On the third try, I put the chocolate in the mixture anyhow, but at the end I was left with a soupy batter with chocolate chunks in it. As others noted, there seems to be too little flour.
    Could you revise the recipe??
    Thanks!

    1. Hey Joely,
      So sorry this recipe did not workout for you. The recipe is correct as is, so there is no need for revision. I would recommend trying a different brand of chocolate, I really like Chocolove, it melts well for me in the microwave. The batter will look runny, but once it has the chance to chill, the cookies should be able to form. I hope this helps for next time! Please let me know if I can help in any other way. Happy Holidays! xTieghan

  6. 4 stars
    These turned out great! Not sure what everything else was talking about with the dough — froze mine for just over an hour and it was the perfect texture! I will admit while I was making it it seemed too liquid-y and it was hard to separate it into two “balls” to chill haha but after that I had no issues. The texture of these cookies is insane – soft on the inside and slightly crinkly on the outside, I loved them! Caramel inside is a great touch too. Only thing I would say is that they are REALLY sweet for my liking. I used dark chocolate instead of milk but I think next time I will try to use dark chocolate chips as well, and not add the sugar. All in all, these are great and I’ll probably make them again! 🙂

    1. Hey Gabriela,
      Thank you so much for giving these cookies a try, I am thrilled that they worked out for you! Happy Holidays! xTieghan

  7. 3 stars
    This recipe was really finicky for me. I tried it three times and couldn’t get the consistency right. The first time I followed the directions exactly, and it came out very soupy. The second time I added more flour and it was far too stiff. The third time I was able to get the consistency to be more like a traditional cookie dough, and it worked well enough but the cookies were cake-like instead of crinkly and gooey. Don’t get me wrong – they taste delicious but I’m not quite sure where I went wrong! The images on this post look so delicious!

    1. Hey Hannah,
      I am so glad you finally got the recipe to work, thanks so much for giving it a try! Happy Holidays! xTieghan

  8. These cookies are phenomenal! I followed the instructions exactly and they are everything advertised: soft, chewy, fudgey goodness.

    But please for the love of all things good FOLLOW THE DIRECTIONS. Does it seem like too little flour? Maybe if you don’t chill it. This recipe is amazingly well written and you have to follow it if you want great results. If you chill it you can definitely scoop and shape these! It will be a little bit messy as your hands melt the chocolate, so try to work quickly. I also sprayed my hands lightly with Pam, which helped.

  9. 3 stars
    I agree with the others in the comments — it seems like there may be a typo in the recipe! I made this with the appropriate amount of flour and my “dough” resembled brownie batter. I added more 1/4 cup at a time until I was able to form little dough balls. In the end I added 1 1/2 cups to the initial 1/2 cup + 2T, so I used 2 cups + 2 T of flour in total. The cookies came out good, but I think I wound up adding a bit too much. I’d love to know the accurate amount! I love the idea of these and know they’d only taste even better 😉

    1. Hey Melyssa,
      Thanks so much for giving the recipe a try! There is no typo in the recipe:) If you follow the measurements as is and chill the batter, you should have great cookies! Happy Holidays! xTieghan

  10. PLEASE UPDATE THE RECIPE! I really wanted to love these cookies, but like many I panicked when I saw the batter that would never become 2 balls. I sadly added 1/1/2 more cups of flour (IF YOU ARE READING THIS, DO NOT ADD EXTRA FLOUR!) and now I have cookies that taste like a mouthful of flour. Please update the recipe to say, ‘Don’t worry, batter can be very wet. Split the batter into 2 wax paper lined bowls, and refrigerate overnight’ as it sounds like most people are doing the same thing I did – which ruins what is probably a great cookie! I love your HBH recipes, but I am SO sad that the instructions didn’t lead me to a better result!

    1. Hey Kathy, if you read the blog post I do mention this, but I will add it to the recipe now. Sorry you had trouble. Please let me know if you have any other questions. I hope you give the cookies another try. Thank you! And Happy Holidays!! xTieghan ?

  11. 5 stars
    I made these again because they were so tasty! Last time I did not get as many, this time I got 30. Left the dough in the fridge overnight but it was still very sticky and my hands were covered. How did you manage not to get it all over you?! I can’t wait to give them out in my Christmas cookie box.

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

  12. 5 stars
    I’m giving this 5 stars because these cookies are AMAZING! But, I do want to share a couple of tips. As the other comments mention this “dough” is really more of a brownie batter. The blog and the recipe both mention chilling the batter but do not specify when this needs to happen. You need to chill the batter before you can even attempt to separate it or roll it out. After adding all the ingredients, I chilled the batter for 2 hours and then separated it into 2 balls and then chilled again for an hour before rolling out. It worked perfectly and they turned out beautifully! These are a keeper!

    Do not panic when you see the “dough” before chilling. As mentioned above it is really more of a batter. Do not add more flour! I tried this on my first batch and the cookies are dense and nothing like this recipe! Trust the chilling process and you won’t regret it!

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

  13. Is this recipe supposed to have more flour? I have double and triple checked the recipe and what I put in and everything is exactly as the recipe calls for but it looks more like a batter than a dough. There’s no way I can divide it in half into to balls.

    1. Hey Danielle,
      The recipe measurements are correct. You need to let the dough chill so you can form the balls. I hope you love the recipe, please let me know if you have any other questions! Happy Holidays! xTieghan